DK1723156T3 - Fremgangsmåde til fremstilling af pyridinderivater - Google Patents

Fremgangsmåde til fremstilling af pyridinderivater Download PDF

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Publication number
DK1723156T3
DK1723156T3 DK04804186.7T DK04804186T DK1723156T3 DK 1723156 T3 DK1723156 T3 DK 1723156T3 DK 04804186 T DK04804186 T DK 04804186T DK 1723156 T3 DK1723156 T3 DK 1723156T3
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propyl
substituted
alkyl
amino
aryl
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DK04804186.7T
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English (en)
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Joachim Gebhardt
Norbert Götz
Hagen Jaedicke
Guido Mayer
Michael Rack
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Dow Agrosciences Llc
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
    • C07C323/50—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton
    • C07C323/51—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton
    • C07C323/60—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and carboxyl groups bound to the same carbon skeleton having the sulfur atoms of the thio groups bound to acyclic carbon atoms of the carbon skeleton with the carbon atom of at least one of the carboxyl groups bound to nitrogen 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
    • C07D213/60—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
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/63—One oxygen atom
    • C07D213/64—One oxygen atom attached in position 2 or 6
    • 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
    • C07D213/62—Oxygen or sulfur atoms
    • C07D213/70—Sulfur atoms
    • C07D213/71—Sulfur atoms to which a second hetero atom is attached
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/40—Esters thereof
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
    • C07F9/02—Phosphorus compounds
    • C07F9/28—Phosphorus compounds with one or more P—C bonds
    • C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
    • C07F9/40—Esters thereof
    • C07F9/4003—Esters thereof the acid moiety containing a substituent or a structure which is considered as characteristic
    • C07F9/4006—Esters of acyclic acids which can have further substituents on alkyl

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Biochemistry (AREA)
  • General Health & Medical Sciences (AREA)
  • Molecular Biology (AREA)
  • Pyridine Compounds (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
  • Indole Compounds (AREA)

Claims (8)

1
1. Fremgangsmåde til fremstilling af substituerede pyridinderivater med formlen (I)
i hvilken R1, R2, der uafhængigt er ens eller forskellige, er H; Ci.2o-alkyl (forgrenet eller li-gekædet eller cyklisk); C6-2o-aryl - hvor hver af disse kan være substitueret med én eller flere af de følgende substituenter: F, Cl, Br, I, Ci-20-alkoxy, C6-2o-aryloxy, amino; F; Cl; Br; I; R3 = CN, N02, C^o-alkyl (forgrenet eller ligekædet eller cyklisk); C6-2o-aryl -hvor hver af disse kan være substitueret med én eller flere af de følgende substituenter: F, Cl, Br, I, Ci-20-alkoxy, C6-2o-aryloxy, amino; F; Cl; Br; I; R4 = EnR6m, hvori hvis n = m =1, er E = S, og R6 = Ci_2o-alkyl (forgrenet eller ligekædet eller cyklisk); C6-2o-aryl - hvor hver af disse kan være substitueret med én eller flere af de følgende substituenter: F, Cl, Br, I, Ci-20-alkoxy, C6-2o-aryloxy, amino; F, Cl, Br, I; hvis n = 0, og m = 1, er R6 = H, Ci_2o-alkyl (forgrenet eller ligekædet eller cyklisk); C6-2o-aryl - hvor hver af disse kan være substitueret med én eller flere af de følgende substituenter: F, Cl, Br, I, Ci-20-alkoxy, C6-2o-aryloxy, amino; F, Cl, Br, I; E1 = O, N; R6= H; n=1 for E1 = O og 2 for E1 = N; omfattende omsætning af en α-β-umættet carbonylforbindelse med formlen (II) R3-C(0)-C(R1)=C(R2)-G (II) 2 i hvilken R1, R2 og R3 har den ovenfor definerede betydning; G = -NH2 eller en fraspaltelig gruppe, —m -< li-----------tu ^mmons-reagens med formlen (Illb2) i hvilken
R' er ens eller forskellig og uafhængigt betyder Ci_20 alkyl, forgrenet eller lige-kædet eller cyklisk, eller C6-2o aryl; EnR6m er således, at hvis n = m = 1, er E = S, og R6 = Ci_2o-alkyl (forgrenet eller ligekædet eller cyklisk); C6-2o-aryl - hvor hver af disse kan være substitueret med én eller flere af de følgende substituenter: F, Cl, Br, I, Ci.2o-alkoxy, C6-2o-aryloxy, amino; F; Cl; Br; I; hvis n = 0, og m = 1, er R6 = H, Ci_2o-alkyl (forgrenet eller ligekædet eller cyklisk); C6-2o-aryl hvor hver af disse kan være substitueret med én eller flere af de følgende substituenter: F, Cl, Br, I, Ci.20-alkoxy, C6-2o-aryloxy, amino; F; Cl; Br; I; Y = -CN; -C(0)NH2; -C(0)0R7 med R7 som defineret for R1 above, undtagen H, i nærvær af en base, og såfremt i) Y = -CN eller C(0)NH2, G = en fraspaltelig gruppe, og basen er et alkoholat, efterfølgende surt katalyseret, med zeoliter katalyseret eller basisk katalyseret ringslutning; ii) Y = -C(0)-0R7, G = en fraspaltelig gruppe, og basen er et alkoholat, efterfølgende basisk ringslutning i nærvær af ammoniak.
2. Fremgangsmåde ifølge krav 1, hvor R1 = R2 = H, og R3 = en elektronfjernende gruppe.
3. Fremgangsmåde ifølge krav 1 til 2, hvor R1 = R2 = H, og R3 er en delvis eller fuldstændigt fluoreret Ci-e-alkylgruppe. 3
4. Fremgangsmåde ifølge krav 1 til 3, hvor R3 = -CF3.
5. Fremgangsmåde ifølge krav 1 til 4 til fremstilling af 4-trifluormethyl-2-pyridi-
hvilken fremgangsmåde omfatter:
kontakt mellem en 4-amino-1,1,1-trifluorbut-3-en-2-on med formlen med et trialkylphosphonoacetat med formlen:
i hvilken R' er som tidligere defineret, og R7 betyder C1-20 alkyl, i nærvær af en base.
6. Phosphorforbindelser med formlen (Illb2)
i hvilken R' er ens eller forskellig og uafhængigt betyder methyl, ethyl, n-propyl, i-propyl, n-butyl, phenyl, tolyl eller benzyl, EnR6m er således, at n = m = 1, E = S, og R6 = methyl, ethyl, propyl, i-propyl, benzyl eller phenyl; 4 Y = -CN; -C(0)NH2; -C(0)0R7 med R7 = methyl.
7. Forbindelser med formlen IV-1 til IV-4
I hvilke de variable har de følgende betydninger: EnR6m er således, at hvis n = m = 1, er E = S, og R6 = methyl, ethyl, propyl, i-propyl, benzyl eller phenyl, hvis η = 0, og m = 1, er R6 = H, methyl, ethyl, propyl, i-propyl, benzyl eller phenyl; Y = -CN; -C(0)NH2; -C(0)0R7 med R7 = methyl, R' er ens eller forskellig og uafhængigt betyder methyl, ethyl, n-propyl, i-propyl, n-butyl, phenyl, tolyl eller benzyl; R3 = trifluormethyl, pentafluorethyl, heptafluorpropyl, heptafluorisopropyl eller pentafluorphenyl; G = -NH2, -NHR1, -N(R1)2j -OR1, F, Cl, Br eller I, hvor R1 er ens eller forskellig og uafhængigt betyder methyl, ethyl, n-propyl, i-propyl, n-butyl, sek.-butyl, tert.-butyl, cyclohexyl, phenyl, tolyl eller benzyl.
8. Forbindelser ifølge krav 6 eller 7 som mellemprodukter ved syntesen af pyrid inderivater.
DK04804186.7T 2003-12-23 2004-12-22 Fremgangsmåde til fremstilling af pyridinderivater DK1723156T3 (da)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
US53161403P 2003-12-23 2003-12-23
EP03029730 2003-12-23
PCT/EP2004/014590 WO2005063780A1 (en) 2003-12-23 2004-12-22 Process for the preparation of pyridine derivatives

Publications (1)

Publication Number Publication Date
DK1723156T3 true DK1723156T3 (da) 2015-04-27

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ID=34923925

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Application Number Title Priority Date Filing Date
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Country Status (16)

Country Link
US (1) US7687632B2 (da)
EP (1) EP1723156B1 (da)
JP (3) JP5160092B2 (da)
KR (1) KR101164694B1 (da)
CN (1) CN1898255B (da)
AR (1) AR046775A1 (da)
AU (1) AU2004309054B2 (da)
BR (1) BRPI0418047B8 (da)
CA (1) CA2550693C (da)
DK (1) DK1723156T3 (da)
ES (1) ES2528716T3 (da)
IL (1) IL176472A (da)
IN (2) IN2012DN02545A (da)
PL (1) PL1723156T3 (da)
WO (1) WO2005063780A1 (da)
ZA (1) ZA200605471B (da)

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MXPA06011589A (es) * 2004-04-08 2006-12-20 Dow Agrosciences Llc Sulfoximinas n-sustituidas insecticidas.
WO2006012320A1 (en) * 2004-06-25 2006-02-02 Dow Agrosciences Llc Process for the preparation of 4-trifluoromethyl-2(1h)-pyridinone
TWI398433B (zh) 2006-02-10 2013-06-11 Dow Agrosciences Llc 殺蟲性之ｎ-取代（６-鹵烷基吡啶-３-基）烷基磺醯亞胺
TWI381811B (zh) * 2006-06-23 2013-01-11 Dow Agrosciences Llc 用以防治可抵抗一般殺蟲劑之昆蟲的方法
BRPI0719053B1 (pt) * 2006-09-01 2016-09-27 Dow Agrosciences Llc inseticidas alquil sulfoximinas (1,3-tiazol 2-substituido) n-substituídas, bem como composição e método para controle de insetos
TWI387585B (zh) * 2006-09-01 2013-03-01 Dow Agrosciences Llc 殺蟲性之ｎ-取代（雜芳基）烷基烴基硫亞胺
TWI395737B (zh) * 2006-11-08 2013-05-11 Dow Agrosciences Llc 作為殺蟲劑之雜芳基（取代的）烷基ｎ-取代的磺醯亞胺
US7709648B2 (en) * 2007-02-09 2010-05-04 Dow Agrosciences Llc Process for the preparation of 2-substituted-5-(1-alkylthio)alkylpyridines
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CN102875548A (zh) * 2011-07-14 2013-01-16 中国科学院大连化学物理研究所 一类基于肟的通过[2+2+2]环加成合成吡啶衍生物的方法
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HUE058180T2 (hu) * 2016-12-01 2022-07-28 Syngenta Participations Ag Eljárás kéntartalmú szubsztituenseket tartalmazó peszticid hatású heterociklusos származékok köztitermékének elõállítására
JP7551622B2 (ja) 2018-12-27 2024-09-17 コルテバ アグリサイエンス エルエルシー スルホンアミド除草剤プロセス中間生成物の調製
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Publication number Publication date
CA2550693C (en) 2013-07-30
PL1723156T3 (pl) 2015-07-31
AU2004309054A1 (en) 2005-07-14
US7687632B2 (en) 2010-03-30
IL176472A (en) 2010-11-30
US20070249837A1 (en) 2007-10-25
EP1723156A1 (en) 2006-11-22
IN2012DN02546A (da) 2015-08-28
KR20060128896A (ko) 2006-12-14
JP2013047245A (ja) 2013-03-07
KR101164694B1 (ko) 2012-07-11
CN1898255A (zh) 2007-01-17
CN1898255B (zh) 2010-06-09
BRPI0418047A (pt) 2007-04-17
AU2004309054B2 (en) 2010-07-08
WO2005063780A1 (en) 2005-07-14
CA2550693A1 (en) 2005-07-14
ZA200605471B (en) 2007-11-28
JP2007519625A (ja) 2007-07-19
IL176472A0 (en) 2006-10-05
ES2528716T3 (es) 2015-02-12
IN2012DN02545A (da) 2015-07-17
EP1723156B1 (en) 2015-01-21
BRPI0418047B1 (pt) 2013-12-31
JP5160092B2 (ja) 2013-03-13
BRPI0418047B8 (pt) 2022-06-28
AR046775A1 (es) 2005-12-21
JP2012214487A (ja) 2012-11-08

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