Synthesis of substituted 3-iodopyrroles by electrophilic cyclization of propargylic aziridines

被引：20
作者：
Yoshida, Masahiro [1 ]
Al-Amin, Mohammad [1 ]
Shishido, Kozo [1 ]
机构：
[1] Univ Tokushima, Grad Sch Pharmaceut Sci, Tokushima 7708505, Japan
来源：
TETRAHEDRON LETTERS | 2009年 / 50卷 / 46期
基金：
日本学术振兴会;
关键词：
STEREOSELECTIVE-SYNTHESIS; ISOQUINOLINES; DERIVATIVES; PYRROLE; FURANS; ALKYNES;
D O I：
10.1016/j.tetlet.2009.09.004
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The electrophilic cyclization of propargylic aziridines is described. 3-Iodopyrroles having a variety of substituents were conveniently synthesized by the reaction of propargylic aziridines with iodine. The resulting substituted 3-iodopyrrole was further functionalized to the tri-substituted pyrroles with high efficiency. (C) 2009 Elsevier Ltd. All rights reserved.
引用
收藏
页码：6268 / 6270
页数：3
相关论文
共 34 条
  • [1] Electrophilic cyclization of o-acetoxy- and o-benzyloxyalkynylpyridines:: An easy entry into 2,3-disubstituted furopyridines
    Arcadi, A
    Cacchi, S
    Di Giuseppe, S
    Fabrizi, G
    Marinelli, F
    [J]. ORGANIC LETTERS, 2002, 4 (14) : 2409 - 2412
  • [2] Functionalized acetylenes as versatile building-blocks for the multicomponent assembling of polysubstituted furans and pyrroles
    Balme, Genevieve
    Bouyssi, Didier
    Monteiro, Nuno
    [J]. HETEROCYCLES, 2007, 73 (01) : 87 - +
  • [3] Intramolecular iodoarylation reaction of alkynes:: easy access to derivatives of benzofused heterocycles
    Barluenga, J
    Trincado, M
    Marco-Arias, M
    Ballesteros, A
    Rubio, E
    González, JM
    [J]. CHEMICAL COMMUNICATIONS, 2005, (15) : 2008 - 2010
  • [4] Synthesis and biological activity of pyrrole, pyrroline and pyrrolidine derivatives with two aryl groups on adjacent positions
    Bellina, Fabio
    Rossi, Renzo
    [J]. TETRAHEDRON, 2006, 62 (31) : 7213 - 7256
  • [5] Highly regio- and stereoselective synthesis of indene derivatives via electrophilic cyclization
    Bi, Hai-Peng
    Guo, Li-Na
    Duan, Xin-Hua
    Gou, Fa-Rong
    Huang, Shu-Hao
    Liu, Xue-Yuan
    Liang, Yong-Min
    [J]. ORGANIC LETTERS, 2007, 9 (03) : 397 - 400
  • [6] CHEN DD, TETRAHEDRON IN PRESS, DOI DOI 10.1016/J.TETLET.2009.05.091
  • [7] Efficient Regio- and Stereoselective Synthesis of 5-Alkyl(aryl)idene- and 5-[Iodoalkyl(aryl)idene]-1H-pyrrol-2(5H)-ones via Electrophilic Cyclization
    Cherry, Khalil
    Duchene, Alain
    Thibonnet, Jerome
    Parrain, Jean-Luc
    Anselmi, Elsa
    Abarbri, Mohamed
    [J]. SYNTHESIS-STUTTGART, 2009, (02): : 257 - 270
  • [8] Counterion Effects in a Gold-Catalyzed Synthesis of Pyrroles from Alkynyl Aziridines
    Davies, Paul W.
    Martin, Nicolas
    [J]. ORGANIC LETTERS, 2009, 11 (11) : 2293 - 2296
  • [9] Highly efficient electrophilic cyclization of N′-(2-alkynylbenzylidene)hydrazides
    Ding, Qiuping
    Chen, Zhiyuan
    Yu, Xingxin
    Peng, Yiyuan
    Wu, Jie
    [J]. TETRAHEDRON LETTERS, 2009, 50 (03) : 340 - 342
  • [10] TRANSITION-METAL CATALYZED-REACTIONS OF ORGANOZINC REAGENTS
    ERDIK, E
    [J]. TETRAHEDRON, 1992, 48 (44) : 9577 - 9648
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