WO2009001942A1 - ３－ヒドロキシプロパン－１－オン化合物、２－プロペン－１－オン化合物およびイソキサゾリン化合物の製造方法 - Google Patents

３－ヒドロキシプロパン－１－オン化合物、２－プロペン－１－オン化合物およびイソキサゾリン化合物の製造方法 Download PDF

Info

Publication number
WO2009001942A1
WO2009001942A1 PCT/JP2008/061771 JP2008061771W WO2009001942A1 WO 2009001942 A1 WO2009001942 A1 WO 2009001942A1 JP 2008061771 W JP2008061771 W JP 2008061771W WO 2009001942 A1 WO2009001942 A1 WO 2009001942A1
Authority
WO
WIPO (PCT)
Prior art keywords
compound
formula
substituted
compound represented
production
Prior art date
Application number
PCT/JP2008/061771
Other languages
English (en)
French (fr)
Inventor
Manabu Yaosaka
Tomohisa Utsunomiya
Yuji Moriyama
Tomohiro Matsumoto
Kazutaka Matoba
Original Assignee
Nissan Chemical Industries, Ltd.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Nissan Chemical Industries, Ltd. filed Critical Nissan Chemical Industries, Ltd.
Priority to JP2009520654A priority Critical patent/JP5349303B2/ja
Priority to US12/452,347 priority patent/US8952175B2/en
Priority to EP08777683A priority patent/EP2172462A4/en
Publication of WO2009001942A1 publication Critical patent/WO2009001942A1/ja
Priority to US14/584,642 priority patent/US9676692B2/en
Priority to US15/586,913 priority patent/US9751821B1/en

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C231/00—Preparation of carboxylic acid amides
    • C07C231/12—Preparation of carboxylic acid amides by reactions not involving the formation of carboxamide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C253/00—Preparation of carboxylic acid nitriles
    • C07C253/30—Preparation of carboxylic acid nitriles by reactions not involving the formation of cyano groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
    • C07C319/14—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides
    • C07C319/20—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of sulfides by reactions not involving the formation of sulfide groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/65—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups
    • C07C45/66—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by splitting-off hydrogen atoms or functional groups; by hydrogenolysis of functional groups by dehydration
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/61—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups
    • C07C45/67—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton
    • C07C45/68—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C45/72—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups
    • C07C45/74—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by reactions not involving the formation of >C = O groups by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by reaction of compounds containing >C = O groups with the same or other compounds containing >C = O groups combined with dehydration
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/82—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups
    • C07C49/83—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups polycyclic
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C49/00—Ketones; Ketenes; Dimeric ketenes; Ketonic chelates
    • C07C49/76—Ketones containing a keto group bound to a six-membered aromatic ring
    • C07C49/82—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups
    • C07C49/835—Ketones containing a keto group bound to a six-membered aromatic ring containing hydroxy groups having unsaturation outside an aromatic ring
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
    • C07C51/353—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by isomerisation; by change of size of the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
    • C07C51/367—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of functional groups containing oxygen only in singly bound form
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
    • C07C51/377—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C65/00—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups
    • C07C65/32—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing keto groups
    • C07C65/40—Compounds having carboxyl groups bound to carbon atoms of six—membered aromatic rings and containing any of the groups OH, O—metal, —CHO, keto, ether, groups, groups, or groups containing keto groups containing singly bound oxygen-containing groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/317—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups
    • C07C67/327—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by splitting-off hydrogen or functional groups; by hydrogenolysis of functional groups by elimination of functional groups containing oxygen only in singly bound form
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
    • C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C67/00—Preparation of carboxylic acid esters
    • C07C67/30—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group
    • C07C67/333—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton
    • C07C67/343—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms
    • C07C67/347—Preparation of carboxylic acid esters by modifying the acid moiety of the ester, such modification not being an introduction of an ester group by isomerisation; by change of size of the carbon skeleton by increase in the number of carbon atoms by addition to unsaturated carbon-to-carbon bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/62—Halogen-containing esters
    • C07C69/65—Halogen-containing esters of unsaturated acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/28—Radicals substituted by singly-bound oxygen or sulphur atoms
    • C07D213/30—Oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/44—Radicals substituted by doubly-bound oxygen, sulfur, or nitrogen atoms, or by two such atoms singly-bound to the same carbon atom
    • C07D213/46—Oxygen atoms
    • C07D213/50—Ketonic radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
    • C07D213/61—Halogen atoms or nitro radicals
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/06—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
    • C07D233/08—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms with alkyl radicals, containing more than four carbon atoms, directly attached to ring carbon atoms
    • C07D233/12—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms with alkyl radicals, containing more than four carbon atoms, directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D233/14—Radicals substituted by oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
    • C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
    • C07D233/60—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms with hydrocarbon radicals, substituted by oxygen or sulfur atoms, attached to ring nitrogen atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
    • C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
    • C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
    • C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
    • C07D261/04—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
    • C07D413/12—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
    • C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Pyridine Compounds (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

Abstract

【課題】　有害生物防除剤の新規な製造中間体を提供する。 【解決手段】 式（４）で表される芳香族ケトン化合物と式（５）で表される置換アセトフェノン化合物を出発原料として、有機溶媒中又は水中で添加物の存在下又は非存在下、塩基存在下、懸濁状態で反応を行うことによる式（３）で表される１，３－ビス（置換フェニル）－３－置換－３－ヒドロキシプロパン－１－オン化合物の製造方法、式（３）で表される化合物の脱水による式（２）で表される１，３－ビス（置換フェニル）－３－置換－２－プロペン－１－オン化合物の製造方法、および、（４）と（５）とから（３）を経由して（２）を１工程で製造する方法。および、（２）とヒドロキシルアミンとを、ハロゲン原子で置換されていてもよい脂肪族又は芳香族炭化水素溶媒中、塩基及び水の存在下で相間移動触媒、C1～C6アルコールおよび非プロトン性極性溶媒から選ばれる添加物を加えて反応させることによる式（１）で表されるイソキサゾリン化合物の製造方法。
PCT/JP2008/061771 2007-06-27 2008-06-27 ３－ヒドロキシプロパン－１－オン化合物、２－プロペン－１－オン化合物およびイソキサゾリン化合物の製造方法 WO2009001942A1 (ja)

Priority Applications (5)

Application Number Priority Date Filing Date Title
JP2009520654A JP5349303B2 (ja) 2007-06-27 2008-06-27 ３−ヒドロキシプロパン−１−オン化合物、２−プロペン−１−オン化合物およびイソキサゾリン化合物の製造方法
US12/452,347 US8952175B2 (en) 2007-06-27 2008-06-27 Method for production of 3-hydroxypropan-1-one compound, method for production of 2-propen-1-one compound and method for production of isoxazoline compound
EP08777683A EP2172462A4 (en) 2007-06-27 2008-06-27 METHOD FOR PRODUCING A 3-HYDROXYPROPAN-1-ON COMPOUND, METHOD FOR PRODUCING A 2-PROPENE-1-ON COMPOUND, AND METHOD FOR PRODUCING AN ISOXAZOLINE COMPOUND
US14/584,642 US9676692B2 (en) 2007-06-27 2014-12-29 Method for production of 3-hydroxypropan-1-one compound, method for production of 2-propen-1-one compound and method for production of isoxazoline compound
US15/586,913 US9751821B1 (en) 2007-06-27 2017-05-04 Method for production of 3-hydroxypropan-1-one compound, method for production of 2-propen-1-one compound and method for production of isoxazoline compound

Applications Claiming Priority (6)

Application Number Priority Date Filing Date Title
JP2007-169151 2007-06-27
JP2007169151 2007-06-27
JP2007-225992 2007-08-31
JP2007225992 2007-08-31
JP2007-293175 2007-11-12
JP2007293175 2007-11-12

Related Child Applications (2)

Application Number Title Priority Date Filing Date
US12/452,347 A-371-Of-International US8952175B2 (en) 2007-06-27 2008-06-27 Method for production of 3-hydroxypropan-1-one compound, method for production of 2-propen-1-one compound and method for production of isoxazoline compound
US14/584,642 Division US9676692B2 (en) 2007-06-27 2014-12-29 Method for production of 3-hydroxypropan-1-one compound, method for production of 2-propen-1-one compound and method for production of isoxazoline compound

Publications (1)

Publication Number Publication Date
WO2009001942A1 true WO2009001942A1 (ja) 2008-12-31

Family

ID=40185751

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2008/061771 WO2009001942A1 (ja) 2007-06-27 2008-06-27 ３－ヒドロキシプロパン－１－オン化合物、２－プロペン－１－オン化合物およびイソキサゾリン化合物の製造方法

Country Status (4)

Country Link
US (3) US8952175B2 (ja)
EP (1) EP2172462A4 (ja)
JP (2) JP5349303B2 (ja)
WO (1) WO2009001942A1 (ja)

Cited By (28)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009025983A2 (en) * 2007-08-17 2009-02-26 E. I. Du Pont De Nemours And Company Method for preparing 5-haloalkyl-4,5-dihydroisoxazole derivatives
WO2010086225A1 (en) 2009-01-29 2010-08-05 Syngenta Participations Ag Insecticidal compounds
JP2011051977A (ja) * 2009-08-03 2011-03-17 Nissan Chem Ind Ltd ジヒドロイソキサゾール置換安息香酸化合物の光学活性体とジアステレオマー塩及びその製造方法
WO2011067272A1 (en) 2009-12-01 2011-06-09 Syngenta Participations Ag Insecticidal compounds based on isoxazoline derivatives
WO2011075591A1 (en) 2009-12-17 2011-06-23 Merial Limited Anti parasitic dihydroazole compounds and compositions comprising same
JP2011519827A (ja) * 2008-04-09 2011-07-14 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー ３−トリフルオロメチルカルコンの調製方法
WO2012007426A1 (en) 2010-07-13 2012-01-19 Basf Se Azoline substituted isoxazoline benzamide compounds for combating animal pests
WO2012060232A1 (ja) * 2010-11-02 2012-05-10 住友化学株式会社 ５－トリフルオロメチル－４－ニトロ－２－イソキサゾリン化合物およびその製造方法
US8231888B2 (en) 2005-12-30 2012-07-31 E.I. Du Pont De Nemours And Company Isoxazolines for controlling invertebrate pests
US8367584B2 (en) 2007-10-03 2013-02-05 E.I. Du Pont De Nemours And Company Naphthalene isoxazoline compounds for control of invertebrate pests
WO2013021949A1 (ja) * 2011-08-05 2013-02-14 日産化学工業株式会社 置換４，４－ジフルオロ－２－ブテン－１－オン化合物及び置換イソキサゾリン化合物の製造方法
US8410153B2 (en) 2007-06-26 2013-04-02 E.I. Du Pont De Nemours And Company Naphthalene isoxazoline invertebrate pest control agents
US8598087B2 (en) 2010-05-27 2013-12-03 E. I. Du Pont De Nemours And Company Crystalline form of 4-[5-[3-chloro-5-(trifluoromethyl)phenyl]-4, 5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-[2-0X0-2-[(2,2,2-trifluoroethyl)amino]ethyl]-1- naph-thalenecarboxamide
US8623875B2 (en) 2007-06-13 2014-01-07 E.I. Du Pont De Nemours And Company Isoxazoline insecticides
JP2014517837A (ja) * 2011-05-18 2014-07-24 シンジェンタ パーティシペーションズ アクチェンゲゼルシャフト アリールチオアセトアミド誘導体をベースとする殺虫化合物
US8853410B2 (en) 2009-04-30 2014-10-07 Basf Se Process for preparing substituted isoxazoline compounds and their precursors
US9006447B2 (en) 2010-11-03 2015-04-14 Basf Se Method for preparing substituted isoxazoline compounds and their precursors 4-chloro, 4-bromo- or 4-iodobenzaldehyde oximes
WO2015066277A1 (en) 2013-11-01 2015-05-07 Merial Limited Antiparisitic and pesticidal isoxazoline compounds
US9073910B2 (en) 2005-12-16 2015-07-07 E.I. Du Pont De Nemours And Company 5-aryl isoxazolines for controlling invertebrate pests
US9085541B2 (en) 2010-06-23 2015-07-21 Basf Se Process for producing imine compounds for combating invertebrate pests
US9126995B2 (en) 2011-11-08 2015-09-08 Nissan Chemical Industries, Ltd. Method for catalytic asymmetric synthesis of optically active isoxazoline compound and optically active isoxazoline compound
US10045969B2 (en) 2004-03-05 2018-08-14 Nissan Chemical Industries, Inc. Isoxazoline-substituted benzamide compound and pesticide
CN109553528A (zh) * 2018-12-21 2019-04-02 荆门医药工业技术研究院 一种2-甲基-4-乙酰基苯甲酸甲酯的合成方法
WO2021038501A1 (en) 2019-08-29 2021-03-04 Pi Industries Ltd. Isoxazoline compounds and their use as pest control agents
US11278533B2 (en) 2007-06-27 2022-03-22 E.I. Du Pont De Nemours And Company Animal pest control method
WO2022123502A1 (en) 2020-12-11 2022-06-16 Pi Industries Ltd. Isoxazoline compounds and their use as pest control agents
CN116178295A (zh) * 2023-01-28 2023-05-30 山东亿盛实业股份有限公司 一种苯唑草酮代谢物t283的制备方法
CN118047728A (zh) * 2024-04-15 2024-05-17 南京道尔医药研究院有限公司 一种氟雷拉纳的制备方法

Families Citing this family (35)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
ES2434734T3 (es) 2008-08-22 2013-12-17 Syngenta Participations Ag Compuestos insecticidas
EP2331515B1 (en) 2008-08-22 2013-07-10 Syngenta Participations AG Insceticidal compounds
EP2331535B1 (en) 2008-09-04 2015-07-22 Syngenta Participations AG Insecticidal compounds
JP2013010740A (ja) * 2011-06-03 2013-01-17 Sumitomo Chemical Co Ltd イソキサゾリン化合物を製造する方法
US9732051B2 (en) 2011-12-23 2017-08-15 Basf Se Isothiazoline compounds for combating invertebrate pests
WO2013119442A1 (en) 2012-02-06 2013-08-15 Merial Limited Parasiticidal oral veterinary compositions comprising systemically-acting active agents, methods and uses thereof
JO3626B1 (ar) 2012-02-23 2020-08-27 Merial Inc تركيبات موضعية تحتوي على فيبرونيل و بيرميثرين و طرق استخدامها
BR112015011441A2 (pt) 2012-11-20 2017-07-11 Merial Inc composições e compostos antihelmínticos e métodos de usos dos mesmos
MX2016013573A (es) 2014-04-17 2017-02-13 Merial Inc Uso de compuestos de malononitrilo para proteger animales de parasitos.
BR112016025076B1 (pt) * 2014-04-30 2022-03-03 Syngenta Participations Ag Processo para a preparação de ciclosserinas substituídas e seus compostos
AU2015264336B2 (en) 2014-05-19 2018-08-30 Boehringer Ingelheim Animal Health USA Inc. Anthelmintic compounds
WO2016069983A1 (en) 2014-10-31 2016-05-06 Merial, Inc. Parasiticidal composition comprising fipronil
UY36570A (es) 2015-02-26 2016-10-31 Merial Inc Formulaciones inyectables de acción prolongada que comprenden un agente activo isoxazolina, métodos y usos de las mismas
JP7045191B2 (ja) 2015-05-20 2022-03-31 ベーリンガー インゲルハイム アニマル ヘルス ユーエスエイ インコーポレイテッド 駆虫性デプシペプチド化合物
HUE056909T2 (hu) 2016-04-06 2022-04-28 Boehringer Ingelheim Animal Health Usa Inc Eljárás enantiomerben dúsított izoxazolinvegyületek elõállítására -(S)-afoxolaner kristályos toluolszolvátja
CN109415280A (zh) 2016-07-07 2019-03-01 巴斯夫欧洲公司 用于制备杀虫环戊烯类化合物的Oxy-Cope重排
JP2019535655A (ja) 2016-10-14 2019-12-12 ベーリンガー インゲルハイム アニマル ヘルス ユーエスエイ インコーポレイテッド 殺虫性及び殺寄生虫性ビニルイソオキサゾリン化合物
JP2020504710A (ja) 2016-11-16 2020-02-13 ベーリンガー インゲルハイム アニマル ヘルス ユーエスエイ インコーポレイテッド 駆虫性デプシペプチド化合物
CN106674143A (zh) * 2016-11-30 2017-05-17 南京林业大学 一种合成3’‑苯甲酰基‑3,3‑二甲基螺{二环[2.2.1]庚‑2,5’‑异噁唑啉}的方法
WO2018166855A1 (en) 2017-03-16 2018-09-20 Basf Se Heterobicyclic substituted dihydroisoxazoles
CN106866447A (zh) * 2017-03-30 2017-06-20 成都绿林科技有限公司 一种合成对乙酰基苯甲酰胺的方法
EP3668866B1 (en) 2017-08-14 2023-01-18 Boehringer Ingelheim Animal Health USA Inc. Pesticidal and parasiticidal pyrazole-isoxazoline compounds
CN107629029A (zh) * 2017-09-19 2018-01-26 安徽省诚联医药科技有限公司 维帕他韦中间体的制备方法
EP3820870A1 (en) 2018-07-09 2021-05-19 Boehringer Ingelheim Animal Health USA Inc. Anthelminthic heterocyclic compounds
CN113260419A (zh) 2018-11-20 2021-08-13 勃林格殷格翰动物保健美国公司 吲唑基氰基乙基氨基化合物、其组合物、其制备方法和其使用方法
CA3133100A1 (en) 2019-03-19 2020-09-24 Boehringer Ingelheim Animal Health USA Inc. Anthelmintic aza-benzothiophene and aza-benzofuran compounds
JP2023528822A (ja) 2020-05-29 2023-07-06 ベーリンガー インゲルハイム アニマル ヘルス ユーエスエイ インコーポレイテッド 駆虫性複素環式化合物
US12065414B2 (en) * 2020-09-03 2024-08-20 Zydus Lifesciences Limited Process for preparation of isoxazoline substituted benzamide compound
US20240116854A1 (en) 2021-01-27 2024-04-11 Intervet Inc. Cyclopropylamide compounds against parasites in fish
CN117355217A (zh) 2021-01-27 2024-01-05 英特威国际有限公司荷兰疫苗厂 对抗鱼类中寄生虫的环丙基酰胺化合物
CN113512007A (zh) * 2021-08-20 2021-10-19 江苏君若药业有限公司 氟雷拉纳的合成
CN113896690B (zh) * 2021-11-22 2023-04-21 常州齐晖药业有限公司 一种异噁唑啉类驱虫药氟雷拉纳的制备方法
CN114315748A (zh) * 2021-12-29 2022-04-12 江苏天和制药有限公司 一种氟雷拉纳的合成方法
CN118715163A (zh) 2022-02-17 2024-09-27 勃林格殷格翰动物保健有限公司 用于提供流体制品邮寄封的方法和系统
CN115477577B (zh) * 2022-10-25 2024-03-15 台州臻挚生物科技有限公司 一种制备2-甲基-4-乙酰基苯甲酸及其衍生物的新方法

Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5514816A (en) 1988-03-18 1996-05-07 Ciba-Geigy Corporation Process for the preparation of substituted difluorobenzo-1,3-dioxoles
WO1996019477A1 (en) 1994-12-22 1996-06-27 Smithkline Beecham Plc Tetracyclic spiro compounds, process for their preparation and their use as 5ht1d receptor antagonists
DE19727042A1 (de) 1996-06-28 1998-01-02 Nippon Mektron Kk Neue Vinyletherverbindung, deren Zwischenprodukte und Verfahren zu deren Herstellung
WO2005085216A1 (ja) 2004-03-05 2005-09-15 Nissan Chemical Industries, Ltd. イソキサゾリン置換ベンズアミド化合物及び有害生物防除剤
JP2007106756A (ja) * 2005-09-14 2007-04-26 Nissan Chem Ind Ltd 置換イソキサゾリン化合物及び有害生物防除剤
WO2007070606A2 (en) * 2005-12-14 2007-06-21 E. I. Du Pont De Nemours And Company Isoxazolines for controlling invertebrate pests
WO2007074789A1 (ja) 2005-12-26 2007-07-05 Nissan Chemical Industries, Ltd. １，３－ビス（置換フェニル）－３－ヒドロキシプロパン－１－オンおよび２－プロペン－１－オン化合物およびその塩

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4215076A (en) * 1976-04-23 1980-07-29 Union Carbide Corporation Surfactant-promoted aldol reactions
US5300689A (en) * 1992-03-20 1994-04-05 Henkel Corporation Oximation process
US5939360A (en) * 1997-07-08 1999-08-17 Nippon Soda Co., Ltd. Compound and herbicidal composition for weed control
WO2000058290A1 (fr) * 1999-03-29 2000-10-05 Nippon Soda Co., Ltd. Procede de preparation de (e)-3-(1-propenyl)isoxazoline
JP2008260691A (ja) * 2007-04-10 2008-10-30 Bayer Cropscience Ag 殺虫性アリールイソオキサゾリン誘導体
TWI649303B (zh) * 2007-08-17 2019-02-01 杜邦股份有限公司 製備４-乙醯基-ｎ-〔２-側氧基-２-〔（２，２，２-三氟乙基）胺基〕乙基〕-１-萘甲醯胺之化合物及方法
TWI518076B (zh) 2008-04-09 2016-01-21 杜邦股份有限公司 製備雜環化合物之方法

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5514816A (en) 1988-03-18 1996-05-07 Ciba-Geigy Corporation Process for the preparation of substituted difluorobenzo-1,3-dioxoles
WO1996019477A1 (en) 1994-12-22 1996-06-27 Smithkline Beecham Plc Tetracyclic spiro compounds, process for their preparation and their use as 5ht1d receptor antagonists
DE19727042A1 (de) 1996-06-28 1998-01-02 Nippon Mektron Kk Neue Vinyletherverbindung, deren Zwischenprodukte und Verfahren zu deren Herstellung
WO2005085216A1 (ja) 2004-03-05 2005-09-15 Nissan Chemical Industries, Ltd. イソキサゾリン置換ベンズアミド化合物及び有害生物防除剤
JP2007106756A (ja) * 2005-09-14 2007-04-26 Nissan Chem Ind Ltd 置換イソキサゾリン化合物及び有害生物防除剤
WO2007070606A2 (en) * 2005-12-14 2007-06-21 E. I. Du Pont De Nemours And Company Isoxazolines for controlling invertebrate pests
WO2007074789A1 (ja) 2005-12-26 2007-07-05 Nissan Chemical Industries, Ltd. １，３－ビス（置換フェニル）－３－ヒドロキシプロパン－１－オンおよび２－プロペン－１－オン化合物およびその塩

Non-Patent Citations (29)

* Cited by examiner, † Cited by third party
Title
"Farmaco", 1971, EDIZIONE SCIENTIFICA, pages: 591 - 596
"Naturforschung, Teil B", ANORGANISCHE CHEMIE, ORGANISCHE CHEMIE, 1977, pages 443 - 446
ARCHIVES OF PHARMACAL RESEARCH, 2004, pages 885 - 892
BULLETIN DES SOCIETES CHIMIQUES BEIGES, 1987, pages 293 - 302
CHEMISTRY LETTERS, 1990, pages 783
CHINESE JOURNAL OF CHEMISTRY, vol. 23, 2005, pages 584 - 588
HETEROCYCLES, vol. 25, 1987, pages 211
JOURNAL OF FLUORINE CHEMISTRY, vol. 113, 2002, pages 105 - 109
JOURNAL OF FLUORINE CHEMISTRY, vol. 125, no. 1, 2004, pages 91 - 94
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1998, pages 989 - 990
JOURNAL OF MOLECULAR CATALYSIS A: CHEMICAL, vol. 181, 2002, pages 179 - 187
JOURNAL OF ORGANIC CHEMISTRY, vol. 71, 2006, pages 3822 - 3828
JOURNAL OF ORGANIC CHEMISTRY, vol. 71, no. 9, 2006, pages 3545 - 3555
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 77, 1980, pages 3657
ORGANIC LETTERS, vol. 7, no. 22, 2005, pages 5103 - 5105
ORGANIC PROCESS RESEARCH AND DEVELOPMENT, vol. 8, 2004, pages 18 - 21
See also references of EP2172462A4
SYNTHESIS, vol. 17, 2005, pages 2901 - 2905
SYNTHETIC COMMUNICATION, 1999, pages 3237 - 3250
SYNTHETIC COMMUNICATIONS, vol. 15, 1985, pages 1291
TETRAHEDRON LETTERS, vol. 21, 1991, pages 2129
TETRAHEDRON LETTERS, vol. 38, 1997, pages 8727 - 8730
TETRAHEDRON LETTERS, vol. 46, 2005, pages 8913 - 8915
TETRAHEDRON, vol. 58, 2002, pages 8263 - 8268
TETRAHEDRON, vol. 58, no. 39, 2002, pages 7775 - 7780
THE JOURNAL OF ORGANIC CHEMISTRY, vol. 56, 1991, pages 1963
THE JOURNAL OF ORGANIC CHEMISTRY, vol. 56, 1991, pages 984
THE JOURNAL OF ORGANIC CHEMISTRY, vol. 64, 1999, pages 2873
ZHURNAL ORGANICHESKOI KHIMII, vol. 26, no. 10, 1990, pages 2205 - 2208

Cited By (60)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US10874645B2 (en) 2004-03-05 2020-12-29 Nissan Chemical Corporation Isoxazoline-substituted benzamide compound and pesticide
US10596157B2 (en) 2004-03-05 2020-03-24 Nissan Chemical Corporation Isoxazoline-substituted benzamide compound and pesticide
US10045969B2 (en) 2004-03-05 2018-08-14 Nissan Chemical Industries, Inc. Isoxazoline-substituted benzamide compound and pesticide
US9073910B2 (en) 2005-12-16 2015-07-07 E.I. Du Pont De Nemours And Company 5-aryl isoxazolines for controlling invertebrate pests
US8552218B2 (en) 2005-12-30 2013-10-08 E.I. Du Pont De Nemours And Company Isoxazolines for controlling invertebrate pests
US8871941B2 (en) 2005-12-30 2014-10-28 E.I. Du Pont De Nemours And Company 8-bromo-5-quinolinecarboxaldehyde oxime
US8231888B2 (en) 2005-12-30 2012-07-31 E.I. Du Pont De Nemours And Company Isoxazolines for controlling invertebrate pests
US8623875B2 (en) 2007-06-13 2014-01-07 E.I. Du Pont De Nemours And Company Isoxazoline insecticides
US9095138B2 (en) 2007-06-13 2015-08-04 E.I. Du Pont De Nemours And Company Isoxazoline insecticides
US8410153B2 (en) 2007-06-26 2013-04-02 E.I. Du Pont De Nemours And Company Naphthalene isoxazoline invertebrate pest control agents
US11278533B2 (en) 2007-06-27 2022-03-22 E.I. Du Pont De Nemours And Company Animal pest control method
WO2009025983A2 (en) * 2007-08-17 2009-02-26 E. I. Du Pont De Nemours And Company Method for preparing 5-haloalkyl-4,5-dihydroisoxazole derivatives
US8217180B2 (en) 2007-08-17 2012-07-10 E.I. Du Pont De Nemours And Company Method for preparing 5-haloalkyl-4,5-dihydroisoxazole derivatives
TWI600639B (zh) * 2007-08-17 2017-10-01 杜邦股份有限公司 製備５-鹵烷基-４，５-二氫異唑衍生物之化合物
JP2014221775A (ja) * 2007-08-17 2014-11-27 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニーＥ．Ｉ．Ｄｕ Ｐｏｎｔ Ｄｅ Ｎｅｍｏｕｒｓ Ａｎｄ Ｃｏｍｐａｎｙ ５−ハロアルキル−４，５−ジヒドロイソキサゾール誘導体を調製する方法
JP2010536767A (ja) * 2007-08-17 2010-12-02 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー ５−ハロアルキル−４，５−ジヒドロイソキサゾール誘導体を調製する方法
US8513431B2 (en) 2007-08-17 2013-08-20 E.I. Du Pont De Nemours And Company Method for preparing 5-haloalkyl-4, 5-dihydroisoxazole derivatives
WO2009025983A3 (en) * 2007-08-17 2009-05-07 Du Pont Method for preparing 5-haloalkyl-4,5-dihydroisoxazole derivatives
AU2008289321B2 (en) * 2007-08-17 2014-02-20 Corteva Agriscience Llc Method for preparing 5-haloalkyl-4,5-dihydroisoxazole derivatives
US8367584B2 (en) 2007-10-03 2013-02-05 E.I. Du Pont De Nemours And Company Naphthalene isoxazoline compounds for control of invertebrate pests
US9035101B2 (en) 2008-04-09 2015-05-19 E.I. Du Pont De Nemours And Company Method for preparing 3-trifluoromethyl chalcones
US9611231B2 (en) 2008-04-09 2017-04-04 E.I. Du Pont De Nemours And Company Method for preparing 3-trifluoromethyl chalcones
US10160731B2 (en) 2008-04-09 2018-12-25 E.I. Du Pont De Nemours And Company Method for preparing 3-trifluoromethyl chalcones
US9938248B2 (en) 2008-04-09 2018-04-10 E.I. Du Pont De Nemours And Company Method for preparing 3-trifluoromethyl chalcones
US9834523B2 (en) 2008-04-09 2017-12-05 E.I. Du Pont De Nemours And Company Method for preparing 3-trifluoromethyl chalcones
US8546618B2 (en) 2008-04-09 2013-10-01 E.I. Du Pont De Nemours And Company Method for preparing 3-trifluoromethyl chalcones
JP2011519827A (ja) * 2008-04-09 2011-07-14 イー・アイ・デュポン・ドウ・ヌムール・アンド・カンパニー ３−トリフルオロメチルカルコンの調製方法
US9527822B2 (en) 2008-04-09 2016-12-27 E.I. Du Pont De Nemours And Company Method for preparing 3-trifluoromethyl chalcones
US20150210654A1 (en) * 2008-04-09 2015-07-30 E.I. Du Pont De Nemours And Company Method for preparing 3-trifluoromethyl chalcones
CN102300864A (zh) * 2009-01-29 2011-12-28 先正达参股股份有限公司 杀虫化合物
WO2010086225A1 (en) 2009-01-29 2010-08-05 Syngenta Participations Ag Insecticidal compounds
US8853410B2 (en) 2009-04-30 2014-10-07 Basf Se Process for preparing substituted isoxazoline compounds and their precursors
JP2011051977A (ja) * 2009-08-03 2011-03-17 Nissan Chem Ind Ltd ジヒドロイソキサゾール置換安息香酸化合物の光学活性体とジアステレオマー塩及びその製造方法
US10750745B2 (en) 2009-12-01 2020-08-25 Syngenta Crop Protection, Llc Insecticidal compounds based on isoxazoline derivatives
US10206400B2 (en) 2009-12-01 2019-02-19 Syngenta Participations Ag Insecticidal compounds based on isoxazoline derivatives
US11357231B2 (en) 2009-12-01 2022-06-14 Syngenta Crop Protection Llc Insecticidal compounds based on isoxazoline derivatives
US9609869B2 (en) 2009-12-01 2017-04-04 Syngenta Crop Protection, Llc Insecticidal compounds based on isoxazoline derivatives
WO2011067272A1 (en) 2009-12-01 2011-06-09 Syngenta Participations Ag Insecticidal compounds based on isoxazoline derivatives
EP3078664A1 (en) 2009-12-17 2016-10-12 Merial Inc. Antiparasitic dihydroazole compositions
US9376434B2 (en) 2009-12-17 2016-06-28 Merial Inc. Antiparisitic dihydroazole compounds and compositions comprising same
US9776999B2 (en) 2009-12-17 2017-10-03 Merial Inc. Antiparisitic dihydroazole compounds and compositions comprising same
US8618126B2 (en) 2009-12-17 2013-12-31 Merial Limited Antiparisitic dihydroazole compounds and compositions comprising same
EP3560923A1 (en) 2009-12-17 2019-10-30 Boehringer Ingelheim Animal Health USA Inc. Anti parasitic dihydroazole compounds and compositions comprising same
WO2011075591A1 (en) 2009-12-17 2011-06-23 Merial Limited Anti parasitic dihydroazole compounds and compositions comprising same
US8598087B2 (en) 2010-05-27 2013-12-03 E. I. Du Pont De Nemours And Company Crystalline form of 4-[5-[3-chloro-5-(trifluoromethyl)phenyl]-4, 5-dihydro-5-(trifluoromethyl)-3-isoxazolyl]-N-[2-0X0-2-[(2,2,2-trifluoroethyl)amino]ethyl]-1- naph-thalenecarboxamide
US9085541B2 (en) 2010-06-23 2015-07-21 Basf Se Process for producing imine compounds for combating invertebrate pests
WO2012007426A1 (en) 2010-07-13 2012-01-19 Basf Se Azoline substituted isoxazoline benzamide compounds for combating animal pests
WO2012060232A1 (ja) * 2010-11-02 2012-05-10 住友化学株式会社 ５－トリフルオロメチル－４－ニトロ－２－イソキサゾリン化合物およびその製造方法
US9006447B2 (en) 2010-11-03 2015-04-14 Basf Se Method for preparing substituted isoxazoline compounds and their precursors 4-chloro, 4-bromo- or 4-iodobenzaldehyde oximes
JP2014517837A (ja) * 2011-05-18 2014-07-24 シンジェンタ パーティシペーションズ アクチェンゲゼルシャフト アリールチオアセトアミド誘導体をベースとする殺虫化合物
JPWO2013021949A1 (ja) * 2011-08-05 2015-03-05 日産化学工業株式会社 置換４，４−ジフルオロ−２−ブテン−１−オン化合物及び置換イソキサゾリン化合物の製造方法
WO2013021949A1 (ja) * 2011-08-05 2013-02-14 日産化学工業株式会社 置換４，４－ジフルオロ－２－ブテン－１－オン化合物及び置換イソキサゾリン化合物の製造方法
US9126995B2 (en) 2011-11-08 2015-09-08 Nissan Chemical Industries, Ltd. Method for catalytic asymmetric synthesis of optically active isoxazoline compound and optically active isoxazoline compound
WO2015066277A1 (en) 2013-11-01 2015-05-07 Merial Limited Antiparisitic and pesticidal isoxazoline compounds
EP3733664A1 (en) 2013-11-01 2020-11-04 Boehringer Ingelheim Animal Health USA Inc. Antiparisitic and pesticidal isoxazoline compounds
CN109553528A (zh) * 2018-12-21 2019-04-02 荆门医药工业技术研究院 一种2-甲基-4-乙酰基苯甲酸甲酯的合成方法
WO2021038501A1 (en) 2019-08-29 2021-03-04 Pi Industries Ltd. Isoxazoline compounds and their use as pest control agents
WO2022123502A1 (en) 2020-12-11 2022-06-16 Pi Industries Ltd. Isoxazoline compounds and their use as pest control agents
CN116178295A (zh) * 2023-01-28 2023-05-30 山东亿盛实业股份有限公司 一种苯唑草酮代谢物t283的制备方法
CN118047728A (zh) * 2024-04-15 2024-05-17 南京道尔医药研究院有限公司 一种氟雷拉纳的制备方法

Also Published As

Publication number Publication date
EP2172462A4 (en) 2010-12-15
US20170233321A1 (en) 2017-08-17
JPWO2009001942A1 (ja) 2010-08-26
US20100137612A1 (en) 2010-06-03
JP5843075B2 (ja) 2016-01-13
US20150119576A1 (en) 2015-04-30
US9751821B1 (en) 2017-09-05
JP5349303B2 (ja) 2013-11-20
US9676692B2 (en) 2017-06-13
EP2172462A1 (en) 2010-04-07
US8952175B2 (en) 2015-02-10
JP2014028810A (ja) 2014-02-13

Similar Documents

Publication Publication Date Title
WO2009001942A1 (ja) ３－ヒドロキシプロパン－１－オン化合物、２－プロペン－１－オン化合物およびイソキサゾリン化合物の製造方法
Zeng et al. Facile synthesis of benzofurans via copper-catalyzed aerobic oxidative cyclization of phenols and alkynes
Liao et al. Palladium-catalyzed benzothieno [2, 3-b] indole formation via dehydrative–dehydrogenative double C–H sulfuration using sulfur powder, indoles and cyclohexanones
Wang et al. GAP chemistry for pyrrolyl coumarin derivatives: a highly efficient one-pot synthesis under catalyst-free conditions
Xie et al. Efficient and mild synthesis of functionalized 2, 3-dihydrofuran derivatives via domino reaction in water
Gu et al. A novel strategy for the construction of substituted benzoxazoles via a tandem oxidative process
WO2006114676A3 (en) A process for the preparation of rupatadine
NZ614088A (en) Process for preparing pyridinamines and novel polymorphs thereof
CN103232336B (zh) 一种取代酮的绿色合成方法
WO2007087175A3 (en) Production of polymers from waste cooking oil
WO2006040527A8 (en) Process for making phenoxy benzamide compounds
Dai et al. Selective oxidation of sulfides to sulfoxides catalysed by deep eutectic solvent with H2O2
WO2009066735A1 (ja) ２－アザアダマンタン類の製造方法
WO2008114506A1 (ja) ４－アミノメチル安息香酸の製造方法
DK2158243T3 (da) Fremgangsmåde til fremstilling af organiske xerogeler
WO2009028676A1 (ja) カルボニル化合物の製造方法およびカルボニル化合物の製造に用いる酸化促進剤
CN103214446B (zh) 一种色满酮衍生物的不对称合成方法
Wang et al. Rapid synthesis of aryl sulfides through metal-free C–S coupling of thioalcohols with diaryliodonium salts
CN106380440B (zh) 一种茚酮并吡咯类衍生物及其合成方法和应用
Sahnoun et al. Cs2CO3 in pyrrolidinone promoted hydration of functionalized (hetero) aryl nitriles under metal-free conditions
AU2016374914B2 (en) Method for producing benzoxazole compound
WO2009137322A3 (en) Processes for the preparation of biphenyl compounds
Zang et al. An efficient one‐pot synthesis of pyrazolone derivatives promoted by acidic ionic liquid
CN106749078B (zh) 一种2-亚胺基恶唑的合成方法
JP5212177B2 (ja) γ−ケトアセタール化合物及びピロール誘導体の製造方法

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 08777683

Country of ref document: EP

Kind code of ref document: A1

ENP Entry into the national phase

Ref document number: 2009520654

Country of ref document: JP

Kind code of ref document: A

NENP Non-entry into the national phase

Ref country code: DE

WWE Wipo information: entry into national phase

Ref document number: 12452347

Country of ref document: US

WWE Wipo information: entry into national phase

Ref document number: 2008777683

Country of ref document: EP

WWE Wipo information: entry into national phase

Ref document number: 451/DELNP/2010

Country of ref document: IN