WO2001014314A1 - Derives de benzene a substituants aromatiques et procedes de preparation de ceux-ci - Google Patents

Derives de benzene a substituants aromatiques et procedes de preparation de ceux-ci Download PDF

Info

Publication number
WO2001014314A1
WO2001014314A1 PCT/JP2000/005532 JP0005532W WO0114314A1 WO 2001014314 A1 WO2001014314 A1 WO 2001014314A1 JP 0005532 W JP0005532 W JP 0005532W WO 0114314 A1 WO0114314 A1 WO 0114314A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
substituted
general formula
same
formula
Prior art date
Application number
PCT/JP2000/005532
Other languages
English (en)
Japanese (ja)
Inventor
Tetsuya Toya
Original Assignee
Nippon Kayaku Kabushiki Kaisha
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
Priority claimed from JP2000009682A external-priority patent/JP2001199934A/ja
Priority claimed from JP2000009700A external-priority patent/JP2001199932A/ja
Application filed by Nippon Kayaku Kabushiki Kaisha filed Critical Nippon Kayaku Kabushiki Kaisha
Publication of WO2001014314A1 publication Critical patent/WO2001014314A1/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C227/00—Preparation of compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C227/04—Formation of amino groups in compounds containing carboxyl groups
    • C07C227/06—Formation of amino groups in compounds containing carboxyl groups by addition or substitution reactions, without increasing the number of carbon atoms in the carbon skeleton of the acid

Definitions

  • biphenyl derivatives have been produced by the following methods: 1) Ullman reaction (Japanese Patent Laid-Open No. 4-2575764), 2) Organometallic compound and halogenated aryl Of copper compounds in the presence of a catalyst such as a Pd complex (Japanese Patent Application Laid-Open No. 5-978113, Japanese Patent Application Laid-Open No. Hei 6-234690), 3) Norolog Method for cupping an aryl compound in the presence of a Ni catalyst and metal powder (Japanese Patent Application Laid-Open No.
  • the present invention provides a novel method for producing a highly selective aromatic ring-substituted benzene derivative using inexpensive raw materials under mild reaction conditions.
  • S0 3 is a R 6 main preparative key cis Le off O group, e preparative key sheet scan Le full O two group, propoxide cis Ruch O group, blanking preparative key Thistle off O group, base down Jiruo key Thistle off O group, etc.
  • the compounds represented by are, for example, alkali metal salts such as sodium salt and potassium salt; alkaline compounds such as magnesium salt and calcium salt. Earth metal salts; transition metal salts such as copper salts and iron salts; and salts which form salts with salts such as organic base salts such as pyridin salts and amine salts. is there . These are also included in the present invention, and they can be provided as salts or as an intermediate by neutralizing a base.
  • the compounds shown may include optical isomers, geometric isomers and tautomers, in which case the invention is directed to one isomer and any proportion of several isomers Mixtures are also included.
  • K0H and NaOH as any alkali metal hydroxide
  • alkali metal hydrides such as NaH
  • organic compounds such as pyridin and triethylamine
  • the amount used is usually from 0.1 to 10 equivalents, preferably from 0.5 to 5 equivalents.
  • Solvents used in the above reaction include, for example, aliphatic alcohols such as methanol, ethanol, aromatic hydrocarbons such as toluene methene, and ethylene. Glycol dimethyl ether triethylene Ether hydrocarbons such as glycol methyl ether, dichloromethanone, 1,2-dichloroethane, etc. Examples include organic chlorine-based hydrocarbons, aliphatic hydrocarbons such as n-hexane, organic acids such as acetic acid, acetonitrile, water, and mixtures thereof. Preferable examples include aliphatic alcohols, aromatic hydrocarbons, aliphatic hydrocarbons, ether hydrocarbons, organic acids, water, and mixtures thereof. This reaction can also be carried out without a solvent.
  • aliphatic alcohols such as methanol, ethanol, aromatic hydrocarbons such as toluene methene, and ethylene.
  • Glycol dimethyl ether triethylene Ether hydrocarbons such as glycol methyl ether, dichlor
  • the reaction temperature is usually from 120 ° C to the reflux temperature of the solvent, and preferably from 0 ° C to the reflux temperature of the solvent.
  • Examples of the acid include organic acids such as acetic acid and p-toluenesulfonic acid.
  • the simple group of the platinum group elements or their salts such as hydrochloric acid are activated carbon, graphite, etc. Ait, silica, aluminum, silica- Even if it is in the form of a suitable simple substance such as aluminum, zeolite, titania, magnesium, zirconia, diatomaceous earth, barium sulfate, etc. Okay.
  • the amount used is usually 0.001 to 20 equivalents, preferably 0.05 to 10 equivalents.
  • oxidation reactions can be carried out in the coexistence of oxygen.
  • purification method examples include recrystallization, distillation, and chromatographic chromatography using silica gel. Purification can be performed using commonly used methods such as
  • halogenating agents such as thionyl chloride, oxylin chloride, and boron tribromide
  • sulfonation such as p-toluenesulfonyl chloride and methansulfonyl chloride
  • Agents such as acetyl chloride Dehydration can also be carried out by the presence reaction of a base such as pyridin or triethylamine. Its usage is usually from 0.5 to 10 equivalents, preferably from 0.8 to 5 equivalents.
  • a purification method it can be purified by a commonly used method such as recrystallization, distillation and chromatography using silica gel.
  • Example 3 4 Preparation of acetylamine 2 — Preparation of ethyl ester of biphenylcarboxylic acid
  • an aromatic-substituted benzene derivative that is useful as an intermediate for pharmaceuticals and agrochemicals, liquid crystals, heat-resistant polymers, liquid crystalline high molecules, and the like can be efficiently produced.
  • This synthesis method uses an inexpensive raw material and does not require special equipment and reaction conditions, and is an efficient industrial method for producing aromatic-substituted benzene derivatives.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne un nouveau procédé de préparation de dérivés de benzène à substituants aromatiques, représentés par la formule générale (4), à partir de matières premières bon marché dans des conditions de réaction modérées et à haut rendement. Dans la formule, X est un noyau benzène éventuellement substitué, un noyau naphtalène éventuellement substitué, un hétérocycle à cinq ou six chaînons éventuellement substitué contenant au moins un élément du groupe comprenant N, O et S, ou un noyau de benzène condensé éventuellement substitué dérivé de ceux-ci; Y représente CO2R6, CN, NO¿2?, SO3R?6, SO¿2NR?4R5, SOR6¿ ou SO¿2?R?6; et R8¿ représente H, COR9 ou CO¿2R?9.
PCT/JP2000/005532 1999-08-20 2000-08-18 Derives de benzene a substituants aromatiques et procedes de preparation de ceux-ci WO2001014314A1 (fr)

Applications Claiming Priority (8)

Application Number Priority Date Filing Date Title
JP11/234693 1999-08-20
JP23469399 1999-08-20
JP36476599 1999-12-22
JP11/364765 1999-12-22
JP2000/9682 2000-01-19
JP2000009682A JP2001199934A (ja) 2000-01-19 2000-01-19 フェノール誘導体、及びその製造法
JP2000009700A JP2001199932A (ja) 2000-01-19 2000-01-19 ベンゼン誘導体、その中間体及びそれらの製造法
JP2000/9700 2000-01-19

Publications (1)

Publication Number Publication Date
WO2001014314A1 true WO2001014314A1 (fr) 2001-03-01

Family

ID=27477591

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2000/005532 WO2001014314A1 (fr) 1999-08-20 2000-08-18 Derives de benzene a substituants aromatiques et procedes de preparation de ceux-ci

Country Status (1)

Country Link
WO (1) WO2001014314A1 (fr)

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2009514867A (ja) * 2005-11-03 2009-04-09 ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング 置換アニシジンの調製方法
US9241942B2 (en) 2007-06-08 2016-01-26 Mannkind Corporation IRE-1α inhibitors

Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2041915A (en) * 1979-01-17 1980-09-17 Mosley A The preparation of bromo-p- terphenyl derivatives
WO1991013616A1 (fr) * 1990-03-08 1991-09-19 Rorer International (Overseas) Inc. NOUVEAUX INHIBITEURS DE HMG-CoA REDUCTASE
JPH07252183A (ja) * 1994-03-12 1995-10-03 Fujirebio Inc フェノール誘導体の製造方法
WO1998050030A1 (fr) * 1997-05-07 1998-11-12 University Of Pittsburgh Inhibiteurs de proteines isoprenyle transferases
JPH1149721A (ja) * 1997-08-01 1999-02-23 Nippon Kayaku Co Ltd ビフェニル誘導体の製造法
JPH1149722A (ja) * 1997-08-01 1999-02-23 Nippon Kayaku Co Ltd ビフェニル誘導体の製造法
WO1999020612A1 (fr) * 1997-10-22 1999-04-29 Astrazeneca Uk Limited Derives imidazoles et leur utilisation comme inhibiteurs de la farnesyle-transferase
WO1999020611A1 (fr) * 1997-10-22 1999-04-29 Zeneca Limited Derives d'imidazole et leur utilisation comme inhibiteurs de la farnesyle-proteine transferase
WO1999041235A1 (fr) * 1998-02-10 1999-08-19 Astrazeneca Uk Limited Inhibiteurs de la farnesyle transferase

Patent Citations (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2041915A (en) * 1979-01-17 1980-09-17 Mosley A The preparation of bromo-p- terphenyl derivatives
WO1991013616A1 (fr) * 1990-03-08 1991-09-19 Rorer International (Overseas) Inc. NOUVEAUX INHIBITEURS DE HMG-CoA REDUCTASE
JPH07252183A (ja) * 1994-03-12 1995-10-03 Fujirebio Inc フェノール誘導体の製造方法
WO1998050030A1 (fr) * 1997-05-07 1998-11-12 University Of Pittsburgh Inhibiteurs de proteines isoprenyle transferases
JPH1149721A (ja) * 1997-08-01 1999-02-23 Nippon Kayaku Co Ltd ビフェニル誘導体の製造法
JPH1149722A (ja) * 1997-08-01 1999-02-23 Nippon Kayaku Co Ltd ビフェニル誘導体の製造法
WO1999020612A1 (fr) * 1997-10-22 1999-04-29 Astrazeneca Uk Limited Derives imidazoles et leur utilisation comme inhibiteurs de la farnesyle-transferase
WO1999020611A1 (fr) * 1997-10-22 1999-04-29 Zeneca Limited Derives d'imidazole et leur utilisation comme inhibiteurs de la farnesyle-proteine transferase
WO1999041235A1 (fr) * 1998-02-10 1999-08-19 Astrazeneca Uk Limited Inhibiteurs de la farnesyle transferase

Non-Patent Citations (8)

* Cited by examiner, † Cited by third party
Title
AUGERI DAVID J. ET AL.: "Potent and orally bioavailable noncysteine-containing inhibitors of protein farnesyltransferase", BIOORG. MED. CHEM. LETT., vol. 9, no. 8, 1999, pages 1069 - 1074, XP002933236 *
BEZBORODOV V.S. ET AL.: "Reduction of 6-acetyl-3-aryl-2-cyclohexanones by sodium borohydride", ZH. ORG. KHIM., vol. 28, no. 7, 1992, pages 1544 - 1545, XP002933231 *
HARRISON ERNEST A. JR.: "Benzodioxole chemistry. 3. (1a)Preparation and selected reactions of 3a,4,7,7a-tetrahydro-4,7-methano-1,3-benzodioxole-2,8-diones. (1b)Novel hydroxide ion induced aromatization of carbonyl-bridged cyclic carbonates", J. ORG. CHEM., vol. 44, no. 11, 1979, pages 1807 - 1811, XP002933232 *
KATRITZKY ALAN R. ET AL.: "Improved syntheses of 3,5-diaryl-substituted phenols", J. ORG. CHEM., vol. 62, no. 23, 1997, pages 8215 - 8217, XP002933230 *
KELLY T. ROSS ET AL.: "A chiral catechol with C2 symmetry", J. ORG. CHEM., vol. 54, no. 4, 1989, pages 980 - 983, XP002933229 *
SAMBAIAH THOTA ET AL.: "Highly regio- and stereoselective cocyclotrimerization and linear cotrimerization of alpha, beta-unsaturated carbonyl compounds with alkynes catalyzed by nickel complexes", J. ORG. CHEM., vol. 64, no. 10, 1999, pages 3663 - 3670, XP002933233 *
SHEN WANG ET AL.: "Potent inhibitors of protein farnesyltransferase: heteroarenes as cysteine replacements", BIOORG. MED. CHEM. LETT., vol. 9, no. 5, 1999, pages 703 - 708, XP002933234 *
YAMAMOTO YOSHIHIKO ET AL.: "Synthesis of phenolic biaryls and p-terphenyls and their heteroaromatic analogs via a cycloaddition route using 4-aryl-2-silyloxybuta-1,3-dienes and electron-deficient alkynes", SYNTHESIS, vol. 8, 1996, pages 949 - 995, XP002933235 *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2009514867A (ja) * 2005-11-03 2009-04-09 ベーリンガー インゲルハイム インターナショナル ゲゼルシャフト ミット ベシュレンクテル ハフツング 置換アニシジンの調製方法
US9241942B2 (en) 2007-06-08 2016-01-26 Mannkind Corporation IRE-1α inhibitors
US9546149B2 (en) 2007-06-08 2017-01-17 Mannkind Corporation IRE-1α inhibitors
US9981901B2 (en) 2007-06-08 2018-05-29 Fosun Orinove Pharmatech, Inc. IRE-1α inhibitors

Similar Documents

Publication Publication Date Title
Chikashita et al. 1, 3-Dimethyl-2-phenylbenzimidazoline as a novel and efficient reagent for mild reductive dehalogenation of. alpha.-halo carbonyl compounds and acid chlorides
CN101208288B (zh) 取代环戊酮的制造方法
WO2021031756A1 (fr) Procédé de synthèse de composés d'acide carboxylique ou de cétone à partir d'alcool ou d'aldéhyde à l'aide d'oxygène ou d'oxygène dans l'air en tant qu'oxydant
Li et al. Weinreb amide directed cross-coupling reaction between electron-deficient alkenes catalyzed by a rhodium catalyst
Bach Preparation of tertiary N, N-dimethylamines by the leuckart reaction
Haruta et al. An effective and selective conjugate propargylation reaction of stannylallenes to. alpha.,. beta.-unsaturated carbonyl compounds and. alpha.-nitro olefins
JPH0339498B2 (fr)
WO2001014314A1 (fr) Derives de benzene a substituants aromatiques et procedes de preparation de ceux-ci
Carpino et al. Benz [f] indene
KR101109942B1 (ko) 방향족 불포화 화합물의 제조 방법
JP2001131121A (ja) ビフェニル誘導体の製造法
WO2001014336A1 (fr) Derives benzeniques substitues par un cycle aromatique, et leur procede de production
JP4517650B2 (ja) テトラヒドロナフタレン及びナフタレン誘導体の製造方法及び製造中間体
JP2001240582A (ja) アニリン誘導体、その中間体及びその製造法
KR20060136357A (ko) 방향족 불포화 화합물의 제조 방법
JP2001199934A (ja) フェノール誘導体、及びその製造法
EP1044956A1 (fr) Procédé de préparation de dérivés de l'acide 2-(4-méthylphényl)benzoique
JP2001131114A (ja) ビフェニル誘導体の製造法
JP2006248952A (ja) ケトンの製造法
JP3008296B2 (ja) ジアリールグリコール酸の製造方法
CA1131253A (fr) Procede d'obtention de cis-bicyclooctylamines
CN106554266B (zh) 一种甲氧基苯乙酸、其中间体及其盐的制备方法
JPH07252183A (ja) フェノール誘導体の製造方法
Wenkert et al. Reaction of the anion of Meldrum's acid with an N-alkylpyridinium salt
JPH1149721A (ja) ビフェニル誘導体の製造法

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): CA CN IN KR US

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): AT BE CH CY DE DK ES FI FR GB GR IE IT LU MC NL PT SE

DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
121 Ep: the epo has been informed by wipo that ep was designated in this application
122 Ep: pct application non-entry in european phase