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Highly Efficient Synthesis of Functionalized Indolizines and Indolizinones by Copper-Catalyzed Cycloisomerizations of Propargylic Pyridines

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Bin Yan, Yebing Zhou, Hao Zhang, Jingjin Chen, and Yuanhong Liu*

State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, People's Republic of China yhliu@mail.sioc.ac.cn

J. Org. Chem., 2007, 72 (20), pp 7783–7786

DOI: 10.1021/jo070983j

Publication Date (Web): August 25, 2007

Section:

Heterocyclic Compounds (One Hetero Atom)

Abstract

The copper-catalyzed cycloisomerizations of 2-pyridyl-substituted propargylic acetates and its derivatives are described, which offer an efficient route to C-1 oxygenated indolizines with a wide range of substituents under mild reaction conditions. The presented method could be readily applied to the synthesis of indolizinones through a cyclization/1,2-migration of tertiary propargylic alcohols.

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This article has been cited by 17 ACS Journal articles (5 most recent appear below).

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Organic Letters2012 Article ASAP
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Synthesis of Pyrazoles via CuI-Mediated Electrophilic Cyclizations of α,β-Alkynic Hydrazones
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Synthesis of NP25302
Kiri Stevens, Andrew J. Tyrrell, Sarah Skerratt, and Jeremy Robertson
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  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
“One-Pot” Multicomponent Approach to Indolizines and Pyrido[1,2-a]indoles
Huajian Zhu, Joachim Stöckigt, Yongping Yu, and Hongbin Zou
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- “One-Pot” Multicomponent Approach to Indolizines and Pyrido[1,2-a]indoles
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  Organic Letters2011 13 (10), 2792-2794
  A new synthetic protocol for efficient and regiospecifc assembly of indolizines and pyrido[1,2-a]indoles by coupling of substituted methyl bromides and alkynes with corresponding pyrrole-2-carboxaldehyde and 1H-indole-2-carboxaldehyde has been developed. ...
  Abstract | Full Text HTML | Hi-Res PDF | PDF w/ Links
Experimental and Computational Exploration of Indolizinyl Carbene Generation. A Route to Biindolizines
Inmaculada R. Lahoz, Carlos Silva López, Armando Navarro-Vázquez, and María-Magdalena Cid
The Journal of Organic Chemistry2011 76 (9), 3266-3273
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  The Journal of Organic Chemistry2011 76 (9), 3266-3273
  In previous work, (E)-2-enynyl pyridines were reported to yield indolizinyl singlet carbenes through base-catalyzed E/Z isomerization followed by a 5-exo-dig pseudocoarctate cyclization. We report herein that in the presence of ethyl acrylate these ...
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