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

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, Email: yhliumail.sioc.ac.cn

B. Yan, Y. Zhou, H. Zhang, J. Chen, Y. Liu, J. Org. Chem., 2007, 72, 7783-7786.

DOI: 10.1021/jo070983j

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Abstract

A copper-catalyzed cycloisomerization of 2-pyridyl-substituted propargylic acetates and its derivatives offers 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.

see article for more examples

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Gold-Catalyzed Multicomponent Synthesis of Aminoindolizines from Aldehydes, Amines, and Alkynes under Solvent-Free Conditions or in Water

B. Yan, Y. Liu, Org. Lett., 2007, 9, 4323-4326.

General and Direct Synthesis of 3-Aminoindolizines and Their Analogues via Pd/Cu-Catalyzed Sequential Cross-Coupling/Cycloisomerization Reactions

Y. Liu, Z. Song, B. Yan, Org. Lett., 2007, 9, 409-412.

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Key Words

indolizines, indolizinones

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ID: J42-Y2007-3130