KR830006186A - 알릴아민 유도체의 제조방법 - Google Patents

알릴아민 유도체의 제조방법 Download PDF

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KR830006186A
KR830006186A KR1019810002699A KR810002699A KR830006186A KR 830006186 A KR830006186 A KR 830006186A KR 1019810002699 A KR1019810002699 A KR 1019810002699A KR 810002699 A KR810002699 A KR 810002699A KR 830006186 A KR830006186 A KR 830006186A
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methyl
alkyl
hydrogen
methoxycarbonylethyl
halogen
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KR840002290B1 (ko
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후벨레 아돌프
엑크하르트 볼프강
리블리 페테르
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아놀드 자일러, 에른스트 알테르
시바-가이기 에이지
에른스트 알테르
시바-가이기에이지
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Abstract

내용 없음

Description

알릴아민 유도체의 제조방법
본 내용은 요부공개 건이므로 전문내용을 수록하지 않았음

Claims (14)

  1. 0°내지 180℃에서 구조식 Ⅱ의 N-알킬화아릴아미노 유도체와
    구조식 Ⅱ의 카르복실산의 N-아실화
    또는 산할로겐화물, 산무수물, 에스테르와의 N-아실화, 또는 구조식 Ⅳ의 N-아실화 아릴아미노 유도체와
    부틸리튬, 소디움 하이드라이드 또는 알킬리 카보네이트의 활성화 그리고 상기 화합물과 구조식 Y 화합물
    의 N-알킬화로 이루어지는 하기 구조식의 화합물의 제조방법.
    상기 식에서
    R은 수소 또는 메틸,
    Ar은 방향족기
    중에서 선택한 기이고 여기서 R1은 C1-C3알콕시 또는 할로겐, R2은 NO2또는 NH2, R3은 수소, C1-C3알킬, C1-C3알콕시 또는 할로겐, R4는 수소 또는 C1-C3알킬, R5는 수소 또는 C1-C3알킬과, R6은 수소, C1-C3알킬, C1-C3알콕시 또는 할로겐 : W는 시아노, -COOR8, -C(R9)=C(R10)(R11) 또는 -C=C-R2, 여기에서 R8은 C1-C3알킬, R9, R10, R11,R12는 각각 수소, C1-C3알킬 또는 할로겐;B는 C3-C4알킬 C2-C4알케닐, 시클로프로필, 2-푸릴, 2-테트라하이드로푸릴, β-(C1-C3알콕시)에틸 또는 CH2Z그룹, 여기에서, Z는 1H-1,2,4-트리아졸릴, 메틸설포닐, X-R13, OSO2-R14또는 -N(R15)(R6), 여기에서 X는 산소 또는 황, R13은 알킬, 알케닐 또는 알키닐기, 각각은 탄소수 4함유, R14는 C1-C3알킬 또는 NH( C1-C3알킬), 과 R12및 R16은 각각 다르다.
  2. 비활성 유기용제에서 반응을 조절하는 제1항에 따른 방법,
  3. 0°내지 150℃에서 반응시키는 제1항에 따른 방법.
  4. 산할로겐화물로서 구조식 Ⅲ의 산염화물 또는 산브롬화물을 사용하는 제1항에 따른 방법.
  5. 구조식 Ⅳ의 치환체 Y가 벤질설포닐옥시, 파라-브로모벤젠 설포닐옥시, 파라-토실옥시, 트리플루오로 아세틸옥시, 저급알킬설포닐옥시, 할로겐으로서 제1항에 따른 방법.
  6. R이 수소 또는 메틸이고, Ar이
    이고, R1이 메틸, 에틸, 메톡시, 에톡시 또는 할로겐; R2가 니트로 또는 아미노;R3와 R6가 각각 수소, 메틸, 에틸, 메톡시, 에톡시, 할로겐; R4와 R5가 각각 수소, 메틸 또는 에틸 W가 CN, COOR8, -C(R6)=C(R10)(R11) 또는 -C≡C-R2, 여기에서 R8은 C1-C3알킬, R9, R10, R11,R12는 각각 수소, 메틸, 염소, 브롬; B가 C1-C3알킬, C2-C4알케닐, 시클로프로필, 2-푸릴, 2-테트라하이드로푸릴, CH2O(C1-C2알킬), 1H-1,2,4-트리아졸릴메틸, CH2SO2CH3, CH2OSO2CH3, CH2OCH2CH=CH2, CH2OCH2C≡CH2, CH2OCH2CH=CH, CH2OCO2NHCH3, CH2N(CH3)2, CH2N(C2H5)2또는 CH2N(C3H7-n)로서 구조식 Ⅰ화합물 제조를 위해서 제1항 내지 제5항의 어느 하나에 따른 방법.
  7. R가 메틸, R1이 메틸, 메톡시, 염소 또는 브롬;R3와 R6가 각각 수소, 메틸, 염소 또는 브롬; R4와 R5가 각각 수소, 메틸 또는 에틸 W가 CN, COOR8, -C(R6)=C(R10)(R11) 또는 -C≡C-R2, 여기에서 R8은 C1-C3알킬, R9, R10, R11,R12는 각각 수소, 메틸 염소, ; B는 2-푸릴, 2-테트라하이드로푸릴, CH2O(C1-C2알킬), 1H-1,2,4-트리아졸릴메틸, CH2SO2CH3, CH2OSO2CH3, CH2OCH2CH=CH2, CH2OCH2C≡CH2, CH2OCO2NHCH3, CH2N(CH3)2, CH2N(C2H5)2또는 CH2N(C3H7-n)로서 구조식 Ⅰ화합물 제조를 위한 제6항에 따른 방법.
  8. Ar가
    이고, R1이 C1-C3알킬, C1-C3알콕시 또는 할로겐, R2가 NO2또는 NH2, R3가 수소, C1-C3알킬, C1-C3알콕시 또는 할로겐, R4가 수소, C1-C3알킬, R5가 수소, C1-C3알킬, R이 수소 또는 메틸로서 항상 오르소 위치에 먼저 치환되고, W는 COOR8, R8은 C1-C3알킬 ; B는 2-푸릴, 2-테트라하이드로푸릴, β-(C1-C2알콕시)에틸 또는 CH2Z, 여기에 Z는 1H-1,2,4-트리아졸릴메틸, 메틸설포닐, X-R13또는 OSO2-R14, 여기에서 X는 산소 또는 황, R13은 알킬, 알케닐 또는 알키닐로서 각각 탄소원자 4함유, 그리고 R14는 C1-C3알킬 또는 NH(C1-C3) 알킬로서 구조식 Ⅰ화합물의 제조를 위한 제1항 내지 제5항의 어느 하나에 따른 방법.
  9. R1이 메틸, 메톡시 또는 할로겐 ; R2는 NO2또는 NH2; R3는 수소, 메틸, 메톡시 또는 할로겐; R4, R5, R은 각각 수소 또는 메틸 ; W는 COOR8, 여기서 R8는 C1-C3알킬 B는 2-푸릴, 2-테트라하이드로푸릴, CH2O(C1-C3)알킬, CH2CH2OCH3, 1H-1,2,4-트리아졸릴메틸, CH2SO2CH3, CH2OSO2CH3, CH2OCH2CH=CH2, CH2OCH2C≡CH2, CH2OCO2NHCH3, 또는 CH2OCH2C≡CH로서 구조식 Ⅰ화합물 제조를 위한 제8항에 따른 방법.
  10. R1이 메틸, R2가 NO2또는 NH2R3가 수소, 메틸, 염소 또는 브롬, R4, R5, R가 각각 수소 또는 메틸, 그리고 R8이 메틸 또는 이소프로필로서, 구조식 Ⅰ화합물의 제조를 위한 제9항에 따른 방법.
  11. Ar가
    이고, R2는 NO2또는 NH2, R3는 수소, C1-C3알킬, C1-C3알콕시 또는 할로겐, R6는 수소, 알킬 또는 할로겐으로서 β-위치에 먼저 치환되고 R는 수소 또는 메틸
    W는 COOR8, R8은 C1-C3알킬 ; B는 2-푸릴, 2-테트라하이드로푸릴, β-(C1-C2알콕시)에틸 또는 CH2Z, 여기에 Z는 1H-1,2,4-트리아졸릴메틸, 설포닐메틸, X-R13또는 OSO2-R14, 여기서 X는 산소 또는 황, R13은 알킬, 알케닐 또는 알키닐로서 각각 탄소원자 4개함유하고, R14는 C1-C3알킬 또는 NH(C1-C3) 알킬로서 구조식 Ⅰ화합물의 제조를 위한 제1항 내지 제5항의 어느 하나에 따른 방법.
  12. R2가 NO2또는 NH2R3가 수소, 메틸, 메톡시, 할로겐 ;R3가 수소, 메틸 또는 할로겐; R가 메틸 또는 수소 ; W가 여기서 R8는 C1-C3알킬 ; 그리고 B는 2-푸릴, 2-테트라하이드로푸릴, CH2O(C1-C3)알킬, CH2CH2OCH3, 1H-1,2,4-트리아졸릴메틸, CH2SO2CH3, CH2OSO2CH3, CH2OCH2CH=CH2, CH2OCH2C≡CH2, CH2OCO2NHCH3, 또는 CH2OCH2C≡CH로서 구조식 Ⅰ화합물 제조를 위한 제11항에 따른 방법.
  13. R가 NO2또는 NH2: R3가 수소, 메틸, 메톡시, 염소 또는 브롬 ; R6가 수소, 메틸, 염소 또는 브롬 R8가 메틸 또는 이소프로필로서, 구조식 Ⅰ화합물의 제조를 위한 제12항에 따른 방법.
  14. 하기의 그룹에서 선택한 화합물의 제조를 위해 제1항 내지 제5항의 어느하나에 따른 방법.
    N-(1´-메톡시카르보닐에틸)-N-메톡시아세틸-2-메틸-6-아미노아닐린,
    N-(1´-메톡시카르보닐에틸)-N-메톡시아세틸-2-메틸-6-니트로아릴린,
    N-(1´-메톡시카르보닐에틸)-N-메톡시아세틸-2,6-디메틸-3-니트로아릴린,
    N-(1´-메톡시카르보닐에틸)-N-에톡시아세틸-2,6-디메틸-3-니트로아릴린,
    N-(1´-이소프로필옥시카르보닐에틸)-N-메톡시아세틸-2,6-디메틸-3-니트로아릴린,
    N-(1´-메톡시카르보닐에틸)-N-메톡시아세틸-2,6-디메틸-3-아미노아닐린,
    N-(1´-메톡시카르보닐에틸)-N-메톡시아세틸-2,3-디메틸-6-아미노아닐린,
    N-(1´-메톡시카르보닐에틸)-N-메톡시아세틸-2,6-디메틸-6-니트로아릴린,
    N-(1´-메톡시카르보닐에틸)-N-(2-푸릴)-2-메틸-6-니트로아릴린,
    N-(1´-메톡시카르보닐에틸)-N-(2-테트라하이드로푸릴)-2-메틸-6-니트로아릴린,
    N-(1´-메톡시카르보닐에틸)-1N-메톡시아세틸-1,2-디아미노나프탈렌,
    N-(1´-메톡시카르보닐에틸)-N-메톡시아세틸아미노-2-니트로나프탈렌,
    N-(1´-메톡시카르보닐에틸)-N-메톡시아세틸아미노-2-메틸-3-니트로나프탈렌.
    N-(1´-메톡시카르보닐에틸)-N-에톡시아세틸아미노-2-메틸-3-니트로나프탈렌.
    N-(1´-이소프로필옥시카르보닐에틸)-N-메톡시아세틸아미노-2-메틸-3-니트로나프탈렌.
    N-(1´-메톡시카르보닐에틸)-N-메톡시아세틸-2-메틸-1,3-디아미노나프탈렌,
    N-(1´-메톡시카르보닐에틸)-1N-메톡시아세틸-3-메틸-1,2-디아미노나프탈렌,
    N-(1´-메톡시카르보닐에틸)-N-메톡시아세틸아미노-3-메틸-3-메틸-2-니트로나프탈렌,
    N-(1´-메톡시카르보닐에틸)-N-(2-푸릴)아미노-2-니트로나프탈렌과
    N-(1´-메톡시카르보닐에틸)-N-(2-테트라하이드로푸릴)아미노-2-니트로나프탈렌,
    ※ 참고사항 : 최초출원 내용에 의하여 공개하는 것임.
KR1019810002699A 1980-07-25 1981-07-25 N-알킬-n-아실아릴아민 유도체의 제조방법 KR840002290B1 (ko)

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US4448773A (en) * 1981-04-29 1984-05-15 Ciba-Geigy Corporation Microbicidal N-alkoxycarbonyl-alkyl-N-substituted acetyl-anilines and -naphthylamines
FR2513993A1 (fr) * 1981-10-06 1983-04-08 Rhone Poulenc Agrochimie Nouveaux fongicides homologues des n-phenyl alaninates et leur procede de preparation et leur application
DE3206235A1 (de) * 1982-02-20 1983-09-01 Bayer Ag, 5090 Leverkusen Substituierte oximinoacetanilide, verfahren zu ihrer herstellung sowie ihre verwendung als schaedlingsbekaempfungsmittel
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FR2667864B2 (fr) * 1990-03-07 1994-08-05 Rhone Poulenc Sante Derives de n-phenyl glycinamides, leur preparation et les medicaments les contenant.
DE4038356A1 (de) * 1990-12-01 1992-06-04 Bayer Ag Verfahren zur racemisierung von optisch aktiven l-aryl-alkylaminen
HU208806B (en) * 1992-03-27 1994-01-28 Nitrokemia Ipartelepek Improved method for producing n-phenyl-n-methoxi-acetyl-d1-alanine-methylesther derivatives
CA2189036A1 (en) * 1994-04-29 1995-11-09 Roland E. Dolle Halomethyl amides as il-1.beta. protease inhibitors
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US4438125A (en) 1984-03-20
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PT73423A (en) 1981-08-01
PL235835A1 (ko) 1982-11-08
DK331781A (da) 1982-01-26
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CA1167044A (en) 1984-05-08
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