[3+2] Cycloaddition reactions of 1-substituted 3,3,3-trifluoropropenes with isonitriles – synthesis of pyrroles and pyrrolines

被引：0
|
作者：
Yuriy N. Markitanov
Vadim M. Timoshenko
Eduard B. Rusanov
Yuriy G. Shermolovich
机构：
[1] Institute of Organic Chemistry,
[2] National Academy of Sciences of Ukraine,undefined
来源：
Chemistry of Heterocyclic Compounds | 2021年 / 57卷
关键词：
ethyl isocyanoacetate; pyrrole; pyrrolidine; pyrroline; sulfamide; sulfone; sulfoximine; tosylmethyl isocyanide; trifluoromethyl group; cycloaddition;
D O I：
暂无
中图分类号：
学科分类号：
摘要：
Cycloaddition reactions of 3,3,3-trifluoropropene derivatives containing an alkoxycarbonyl, sulfonyl, sulfoximine, or sulfamide substituent in position 1 with ethyl isocyanoacetate proceed with the formation of 3-(trifluoromethyl)-2,3-dihydro-1H-pyrroles, whereas their reactions with tosylmethyl isocyanide lead to the formation of 4-(trifluoromethyl)-1H-pyrroles.
引用
收藏
页码：253 / 260
页数：7
相关论文
共 50 条
  • [21] Access to thiazoles via [3+2] cycloaddition of 1,2,3-thiadiazoles with isonitriles
    An, Qiaoyu
    Liu, Lei
    Tang, Zongyuan
    Luo, Han
    Li, You
    Xu, Mingchuan
    Li, Baosheng
    ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (12) : 2909 - 2913
  • [22] Synthesis of stereochemically diverse 2-pyrrolines through a novel Ag catalyzed [3+2] cycloaddition
    Bishop, Joshua A.
    Schaus, Scott E.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2010, 240
  • [23] AN EFFICIENT SYNTHESIS OF 1,2,3,4-TETRASUBSTITUTED PYRROLES VIA INTRAMOLECULAR AZOMETHINE YLIDE [3+2]-DIPOLAR CYCLOADDITION
    TOYOTA, M
    NISHIKAWA, Y
    FUKUMOTO, K
    HETEROCYCLES, 1994, 39 (01) : 39 - 42
  • [24] Synthesis of substituted alkylsilylacetonitriles and their application in a novel [3+2] cycloaddition.
    McGaulley, P
    Hall, J
    Anna, LJ
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2002, 223 : U292 - U292
  • [25] Synthesis of substituted imidazolines via [3+2]-cycloaddition of aziridines with nitriles
    Prasad, BAB
    Pandey, G
    Singh, VK
    TETRAHEDRON LETTERS, 2004, 45 (06) : 1137 - 1141
  • [26] Synthesis of 3-pyrrolines, annulated 3-pyrrolines, and pyrroles from α-Amino allenes
    Dieter, RK
    Yu, H
    ORGANIC LETTERS, 2001, 3 (24) : 3855 - 3858
  • [27] (3+2)-Cycloaddition Reactions of Oxyallyl Cations
    Wu, Jimmy
    SYNTHESIS-STUTTGART, 2015, 47 (01): : 22 - 33
  • [28] Dearomative Indole (3+2) Cycloaddition Reactions
    Li, Hui
    Hughes, Russell P.
    Wu, Jimmy
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (17) : 6288 - 6296
  • [29] [3+2]CYCLOADDITION REACTIONS OF NITRONES WITH ISOTHIOCYANATES
    ZINNER, G
    EGHTESSAD, E
    ARCHIV DER PHARMAZIE, 1979, 312 (11) : 907 - 913
  • [30] Theoretical studies of [3+2]-cycloaddition reactions
    Kuznetsov, M. L.
    USPEKHI KHIMII, 2006, 75 (11) : 1045 - 1073
12345