A Direct Phosphine-Mediated Synthesis of Pyrroles from Acid Chlorides and α,β-Unsaturated Imines

被引:78
作者
Lu, Yingdong [1 ]
Arndtsen, Bruce A. [1 ]
机构
[1] McGill Univ, Dept Chem, Montreal, PQ H3A 2K6, Canada
关键词
HIGHLY SUBSTITUTED PYRROLES; ONE-POT; REGIOSELECTIVE SYNTHESIS; PROPARGYLIC ALCOHOLS; BIOLOGICAL-ACTIVITY; LAMELLARIN-O; LUKIANOL-A; CONDENSATION; ALKALOIDS; ALKYNES;
D O I
10.1021/ol900185n
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A one-step method to assemble pyrroles from alpha,beta-unsaturated imines and acid chlorides has been developed. This reaction is mediated by triphenylphosphine, which eliminates phosphine oxide to allow cyclization. This reaction has been employed to access a diverse range of pyrroles via modulation of the two building blocks and applied as well to the synthesis of lukianol A.
引用
收藏
页码:1369 / 1372
页数:4
相关论文
共 50 条
  • [1] A direct phosphine-mediated synthesis of polyfunctionalized pyrroles from arylglyoxals and β-enaminones
    Masoudi, Mozhgan
    Anary-Abbasinejad, Mohammad
    TETRAHEDRON LETTERS, 2016, 57 (01) : 103 - 104
  • [2] A New Method for the Synthesis of Multisubstituted Pyrroles of Biological Interest by Double Nucleophilic Addition to α,β-Unsaturated Imines
    Takahashi, Atsushi
    Kawai, Shiho
    Hachiya, Iwao
    Shimizu, Makoto
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (01) : 191 - 200
  • [3] Synthesis of Tetrasubstituted Pyrroles from Terminal Alkynes and Imines
    Hu, Yancheng
    Wang, Chunxiang
    Wang, Dongping
    Wu, Fan
    Wan, Boshun
    ORGANIC LETTERS, 2013, 15 (12) : 3146 - 3149
  • [4] BrØnsted acid-promoted synthesis of polysubstituted pyrroles from enamines/imines and diazopyruvates: A metal-free cascade approach
    Sajjad, Farrukh
    Xu, Ming-Hua
    GREEN SYNTHESIS AND CATALYSIS, 2025, 6 (01): : 86 - 90
  • [5] A Phosphine-Mediated Synthesis of 1,4-Oxazepine- and 1,5-Oxazocine-Based Sugar Hybrids from Deoxysugar Azides
    Kurhade, Suresh E.
    Salunkhe, Videsh T.
    Siddaiah, V.
    Bhuniya, Debnath
    Reddy, D. Srinivasa
    SYNTHESIS-STUTTGART, 2011, (21): : 3523 - 3529
  • [6] Phosphine-mediated cascade reaction of azides with MBH-acetates of acetylenic aldehydes to substituted pyrroles: a facile access to N-fused pyrrolo-heterocycles
    Reddy, Chada Raji
    Reddy, Motatipally Damoder
    Srikanth, Boinapally
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2012, 10 (21) : 4280 - 4288
  • [7] Direct synthesis of pentasubstituted pyrroles and hexasubstituted pyrrolines from propargyl sulfonylamides and allenamides
    Ye, Changqing
    Jiao, Yihang
    Chiou, Mong-Feng
    Li, Yajun
    Bao, Hongli
    CHEMICAL SCIENCE, 2021, 12 (26) : 9162 - 9167
  • [8] Efficient synthesis of fluorinated α- and β-amino nitriles from fluoroalkylated α,β-unsaturated imines
    Palacios, Francisco
    Ochoa de Retana, Ana M.
    Pascual, Sergio
    Fernandez de Troconiz, Guillermo
    TETRAHEDRON, 2011, 67 (08) : 1575 - 1579
  • [9] CO- and HCl-free synthesis of acid chlorides from unsaturated hydrocarbons via shuttle catalysis
    Fang, Xianjie
    Cacherat, Bastien
    Morandi, Bill
    NATURE CHEMISTRY, 2017, 9 (11) : 1105 - 1109
  • [10] Phosphine-Catalyzed [4+1] Annuiation between α,β-Unsaturated Imines and Allylic Carbonates: Synthesis of 2-Pyrroilines
    Tian, Junjun
    Zhou, Rong
    Sun, Haiyun
    Song, Haibin
    He, Zhengjie
    JOURNAL OF ORGANIC CHEMISTRY, 2011, 76 (07) : 2374 - 2378