Literature DB >> 19320503

Synthesis of pyrroles by consecutive multicomponent reaction/[4 + 1] cycloaddition of alpha-iminonitriles with isocyanides.

Patrice Fontaine1, Géraldine Masson, Jieping Zhu.   

Abstract

[4 + 1] Cycloaddition of alpha,beta-unsaturated imidoyl cyanide (2-cyano-1-azadienes) with isocyanides in the presence of a catalytic amount of AlCl(3) afforded polysubstituted 2-amino-5-cyanopyrroles in good to excellent yields. In combination with the IBX/TBAB-mediated oxidative Strecker reaction, this important heterocycle is readily synthesized in two steps from simple starting materials.

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Year:  2009        PMID: 19320503     DOI: 10.1021/ol9001619

Source DB:  PubMed          Journal:  Org Lett        ISSN: 1523-7052            Impact factor:   6.005


  6 in total

Review 1.  Comprehensive survey of chemical libraries for drug discovery and chemical biology: 2009.

Authors:  Roland E Dolle; Bertrand Le Bourdonnec; Karin Worm; Guillermo A Morales; Craig J Thomas; Wei Zhang
Journal:  J Comb Chem       Date:  2010-10-05

2.  One-pot multicomponent synthesis of diversely substituted 2-aminopyrroles. A short general synthesis of rigidins A, B, C, and D.

Authors:  Liliya V Frolova; Nikolai M Evdokimov; Kathryn Hayden; Indranil Malik; Snezna Rogelj; Alexander Kornienko; Igor V Magedov
Journal:  Org Lett       Date:  2011-01-26       Impact factor: 6.005

3.  One pot three component reaction for the rapid synthesis of pyrrolo[1,2-a]benzimidazoles.

Authors:  Wei-Shun Hsu; Vijaykumar Paike; Chung-Ming Sun
Journal:  Mol Divers       Date:  2013-03-26       Impact factor: 2.943

4.  Atom-economic generation of gold carbenes: gold-catalyzed formal [3+2] cycloaddition between ynamides and isoxazoles.

Authors:  Ai-Hua Zhou; Qiao He; Chao Shu; Yong-Fei Yu; Shuang Liu; Tian Zhao; Wei Zhang; Xin Lu; Long-Wu Ye
Journal:  Chem Sci       Date:  2014-11-12       Impact factor: 9.825

5.  From Isocyanides to Iminonitriles via Silver-mediated Sequential Insertion of C(sp3)-H Bond.

Authors:  Huiwen Chi; Hao Li; Bingxin Liu; Rongxuan Ye; Haoyang Wang; Yin-Long Guo; Qitao Tan; Bin Xu
Journal:  iScience       Date:  2019-11-01

6.  Direct synthesis of pentasubstituted pyrroles and hexasubstituted pyrrolines from propargyl sulfonylamides and allenamides.

Authors:  Changqing Ye; Yihang Jiao; Mong-Feng Chiou; Yajun Li; Hongli Bao
Journal:  Chem Sci       Date:  2021-06-08       Impact factor: 9.825

  6 in total

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