Synthesis of N,N-disubstituted 1-cyanocyclopropanecarboxamides

被引:5
|
作者
Yamagata, K [1 ]
Okabe, F [1 ]
Tagawa, Y [1 ]
机构
[1] Fukuoka Univ, Fac Pharmaceut Sci, Fukuoka 8140180, Japan
关键词
acetyl chloride; cyclization; cyclopropanes; furans; ring opening;
D O I
10.1002/ejoc.200200516
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
2-(Disubstituted amino) -4,5-dihydro-3-furancarbonitriles 1a-i reacted with acetyl chloride to yield the corresponding ring-opening products 2a-i The cyclization of compounds 2a-i with bases gave the corresponding N,N-disubstituted 1-cyanocyclopropanecarboxamides 3a-c and (E)-1-cyano-2-phenylcyclopropanecarboxamides MA The same compounds 3d-f were also obtained by treatment of compounds 2g-i with sodium methoxide. ((C) Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003).
引用
收藏
页码:2383 / 2387
页数:5
相关论文
共 50 条
  • [1] SYNTHESIS OF ISOMERIC S,N-DISUBSTITUTED AND N,N-DISUBSTITUTED DIPHENYLPHOSPHINOTHIOIMIDOESTER AND DIPHENYLPHOSPHINOTHIOFORMAMIDE
    ANTONIADIS, A
    BRUNS, A
    KUNZE, U
    PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, 1983, 15 (03): : 317 - 319
  • [2] SYNTHESIS OF N,N-DISUBSTITUTED DITHIOOXAMIDES
    ZIELKE, R
    MAGERLEIN, H
    SYNTHESIS-STUTTGART, 1975, (01): : 47 - 48
  • [3] SYNTHESIS OF N,N-DISUBSTITUTED AMINOACETOPHENONES
    TERPUGOVA, MP
    AMOSOV, YI
    KOTLYAREVSKII, IL
    MYASNIKOVA, RN
    BULLETIN OF THE ACADEMY OF SCIENCES OF THE USSR DIVISION OF CHEMICAL SCIENCE, 1976, 25 (03): : 650 - 651
  • [4] Synthesis of N,N-disubstituted aminomethylenediphosphonates and their derivatives
    A. A. Prishchenko
    M. V. Livantsov
    O. P. Novikova
    L. I. Livantsova
    I. S. Ershov
    V. S. Petrosyan
    Russian Journal of General Chemistry, 2012, 82 : 1593 - 1595
  • [5] SYNTHESIS OF N,N-DISUBSTITUTED THIOCARBAMOYL BROMIDES
    WALTER, W
    BECKER, RF
    ANNALEN DER CHEMIE-JUSTUS LIEBIG, 1970, 733 : 195 - &
  • [6] NOVEL SYNTHESIS OF N,N-DISUBSTITUTED THIONOCARBAMATES
    DAMICO, JJ
    BOLLINGE.FG
    SULLIVAN, AB
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 1973, (AUG26): : 36 - 36
  • [7] Synthesis of N,N-disubstituted (meth)acrylamides
    Kazakov, SA
    Kazantsev, OA
    Shirshin, KV
    Danov, SM
    Igolkin, AV
    Afon'shin, GN
    RUSSIAN JOURNAL OF APPLIED CHEMISTRY, 2000, 73 (05) : 912 - 913
  • [8] Synthesis of N,N-disubstituted aminomethylenediphosphonates and their derivatives
    Prishchenko, A. A.
    Livantsov, M. V.
    Novikova, O. P.
    Livantsova, L. I.
    Ershov, I. S.
    Petrosyan, V. S.
    RUSSIAN JOURNAL OF GENERAL CHEMISTRY, 2012, 82 (09) : 1593 - 1595
  • [9] SYNTHESIS AND REACTION OF 1-(N,N-DISUBSTITUTED AMINO)PYRAZOLES
    KISHIMOTO, S
    NOGUCHI, S
    MASUDA, K
    CHEMICAL & PHARMACEUTICAL BULLETIN, 1976, 24 (12) : 3001 - 3010
  • [10] A NEW SYNTHESIS OF N,N-DISUBSTITUTED AMIDE THIOKETALS
    OKECHA, SA
    CHEMISTRY & INDUSTRY, 1983, (05) : 205 - 206