KR940005574A - 2,5-이치환된 피리딘의 제조방법 - Google Patents

2,5-이치환된 피리딘의 제조방법 Download PDF

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KR940005574A
KR940005574A KR1019930013014A KR930013014A KR940005574A KR 940005574 A KR940005574 A KR 940005574A KR 1019930013014 A KR1019930013014 A KR 1019930013014A KR 930013014 A KR930013014 A KR 930013014A KR 940005574 A KR940005574 A KR 940005574A
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alkyl
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KR1019930013014A
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KR100293858B1 (ko
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크라우스 헬무트
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만프레트 조벨·요아힘 그렘
바이엘 아크티엔게젤샤프트
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    • 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
    • C07D213/61—Halogen atoms or nitro radicals

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

Abstract

본 발명은 일반식(Ⅱ)의 엔아민을 일반식(Ⅲ)의 β-아미노-아크릴로니트릴과 반응시키고, 4-R1-5-아미노-펜타-2,4-디에노니트릴을 나타내는 개쇄 중간체를 양자산 또는 암모니아로 처리하여 일반식(I)의 2,5-이 치환된 피리딘을 제조하는 방법에 관한 것이다.

Description

2,5-이치환된 피리딘의 제조방법
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (9)

  1. -70℃ 내지 +50℃ 바람직하게는 -40℃내지 +25℃의 온도범위에서, 액상중, 0.7 내지 20당량, 바람직하게는 1내지 10당량의 C1-C8-카복실산의 존재하에, 0.2내지 5몰, 바람직하게는 0.4내지 3몰, 특히 바람직하게는 0.7 내지 1.5몰의 일반식 (Ⅱ)의 엔아민을 1몰의 일반식(Ⅲ)의 β-아미노-아크릴로니트릴과 반응시켜 개쇄 중간체를 수득한 후, C1-C8-카복실산, 할로겐화된 탄화수소, 알콜, 아미드 또는 이들의 혼합물로 이루어진 반응 매질중에서, 0.7내지 12당량, 바람직하게는 1 내지 6당량의 양자산 또는 암모니아로 폐환반응시킴을 특징으로 하여, 일반식(I)의 2.5-이치환된 피리딘을 제조하는 방법.
    상기 식에서, R1, R2, R3, R4및 R5는 서로 독립적으로 직쇄 또는 측쇄 C1-C8-알킬, C2-C8알케닐, C2-C8알콕시알킬, C3-C8-알콕시알케닐, C3-C8-사이클로알킬, C6-C12-아릴, C7-C10-아르알킬 또는 포화 또는 불포화된 5- 내지 8-원 헤테로사이클릭 환(이의 헤테로원자는 N, 0 및 5로 이루어진 그룹중에서 선택된 1또는 2개이다)이고, 추가로 R2와 R3또는 R4와 R5는 각각의 경우에 서로 독립적으로 이들이 치환하는 N원자와 함께, N, O및 S로 이루어진 그룹중의 헤테로원자를 추가로 포함할 수 있는 5- 내지 8-원 환을 형성할 수 있으며. X는 염소, 브롬, 하이드록실 또는 아미노이다.
  2. 제1항에 있어서, 직쇄 또는 측쇄된 C1-C8-알킬, 사이클로프로필, 사이클로펜틸, 사이클로헥실, 페닐 또는 벤질을 나타내는 치환체 R11이 R1의 위치를 가짐을 특징으로 하는 방법.
  3. 제2항에 있어서. 직쇄 또는 측쇄된 C1-C4-알킬을 나타내는 치환체 R21이 R11의 위치를 가짐을 특징으로 하는 방법.
  4. 제1항에 있어서. R2, R3, R4및 R5의 위치를 서로 독립적으로 직쇄 또는 측쇄된 C1-C8-알킬, 사이클로프로필, 사이클로펜틸, 사이클로헥실, 페닐 또는 벤질을 나타내는 치환체 R12, R13, R14및 R15가 차지하고, 추가로 R12와 R13또는 R14와 R15가 각각의 경우에 서로 독립적으로 이들이 치환하는 N원자와 함께 N, 0 및 S로 이루어진 그룹으로부터의 추가의 헤테로원자를 포함할 수 있는 5- 내지 8-원 환을 형성함을 특징으로 하는 방법.
  5. 제5항에 있어서, R12, R13, R14및 R15의 위치를 서로 독립적으로 직쇄 또는 측쇄된 C1-C4-알킬을 나타내는 치환체 R22, R23, R24및 R25가 차지하고, 추가로 R22와 R23또는 R24와 R25가 각각의 경우에 서로 독립적으로 이들이 치환하는 N원자와 함께 C1-C4-알킬 또는 하이드록시-C1-C4-알킬에 의해 치환될 수 있는 모르폴리노, 피롤리딘, 또는 피페리딘을 나타냄을 특징으로 하는 방법.
  6. 제1항에 있어서, 개쇄 중간체를 수득하기 위한 반응에 카복실산으로서 아세트산 또는 프로피온산, 바람직하게는 아세트산을 사용하는 방법.
  7. 제1항에 있어서, 할로겐화된 탄화수소, 케톤, 니트릴, 아미드, 에스테르 및 에테르로 이루어진 그룹으로부터의 용매 또는 이들 다수의 혼할물을 개쇄 중간체 수득 반응을 위한 액상조절에 사용하는 방법.
  8. 제7항에 있어서. 하나 이상의 할로겐화된 탄화수소를 사용하는 방법.
  9. 제1항에 있어서, 폐환 반응을 카복실산과 할로겐화된 탄화수소의 혼합물중에서 수행하는 방법.
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019930013014A 1992-07-13 1993-07-12 2,5-이치환된피리딘의제조방법 KR100293858B1 (ko)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE4223013A DE4223013A1 (de) 1992-07-13 1992-07-13 Verfahren zur Herstellung von 2,5-disubstituierten Pyridinen
DEP4223013.6 1992-07-13

Publications (2)

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KR940005574A true KR940005574A (ko) 1994-03-21
KR100293858B1 KR100293858B1 (ko) 2001-09-17

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US (1) US5466800A (ko)
EP (1) EP0584491B1 (ko)
JP (1) JP3243072B2 (ko)
KR (1) KR100293858B1 (ko)
DE (2) DE4223013A1 (ko)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5508410A (en) * 1993-11-30 1996-04-16 Reilly Industries, Inc. Process for preparing 2-halo-5-substituted pyridines
ES2221696T3 (es) * 1997-08-19 2005-01-01 F. Hoffmann-La Roche Ag Procedimiento para la preparacion de piridinas 2,5.disustituidas.
CN111393387B (zh) * 2020-04-17 2022-12-30 江苏扬农化工集团有限公司 一种微通道反应器合成吡虫啉中间体吗啉基丙烯的方法
CN114790173B (zh) * 2022-04-29 2023-08-01 浙江南郊化学有限公司 1-甲基-3-二氟甲基吡唑-4-甲酸绿色合成工艺

Family Cites Families (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE240010C (ko) *
US4348396A (en) * 1978-01-23 1982-09-07 Hoffmann-La Roche Inc. Substituted 11-oxo-11H-pyrido[2,1-b]quinazolines and method of inhibiting allergic reactions with them
US4319024A (en) * 1979-03-29 1982-03-09 Dynamit Nobel Aktiengesellschaft Method of preparing β-alkoxyacrlonitriles
EP0018473B1 (de) * 1979-03-29 1982-12-29 Hüls Troisdorf Aktiengesellschaft Verfahren zur Herstellung von beta-Alkoxy-acrylnitrilen, 3-Amino-acrylnitrilen und 2-Cyano-vinylestern
FI820573L (fi) * 1981-03-03 1982-09-04 Lilly Co Eli 1-bentsoyl-3-(arylpyridyl)ureafoereningar beroerande eller till dessa hoerande foerbaettringar
US4405552A (en) * 1981-03-03 1983-09-20 Eli Lilly And Company 1-Benzoyl-3-(arylphyridyl)urea compounds
US4473696A (en) * 1982-10-07 1984-09-25 Ici Americas Inc. Synthesis of 2-substituted-5-methyl-pyridines
AU571683B2 (en) * 1984-05-23 1988-04-21 Zeneca Ag Products Inc. 2-substituted-5-methylpyridines from methylcyclobutane- carbonitrile, valeronitrile and pentenonitrile intermediates
DD240010A1 (de) * 1985-03-22 1986-10-15 Univ Berlin Humboldt Verfahren zur herstellung von substituierten 2-imino-1h-pyridin-1-aminen
JPH0717621B2 (ja) * 1986-03-07 1995-03-01 日本バイエルアグロケム株式会社 新規ヘテロ環式化合物

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DE59300178D1 (de) 1995-06-08
EP0584491A1 (de) 1994-03-02
EP0584491B1 (de) 1995-05-03
JPH07291933A (ja) 1995-11-07
JP3243072B2 (ja) 2002-01-07
US5466800A (en) 1995-11-14
DE4223013A1 (de) 1994-01-20
KR100293858B1 (ko) 2001-09-17

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