Synfacts 2007(12): 1249-1249  
DOI: 10.1055/s-2007-991403
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

Copper-Catalyzed Heteroannulation of Propargylic Pyridines to Indolizines

Contributor(s): Victor Snieckus, Toni Rantanen
B. Yan, Y. Zhou, H. Zhang, J. Chen, Y. Liu*
Shanghai Institute of Organic Chemistry, P. R. of China
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Publication History

Publication Date:
22 November 2007 (online)


A variety of propargylic pyridines were converted into the corresponding functionalized indolizines or indolizinones under copper catalysis in good to excellent yields. The presence of a base significantly accelerates the rate of the reaction (2 h vs. 18 h with and without base, respectively). Propargylic secondary acetates lead to indolizines and propargylic tertiary alcohols to indolizinones, the latter reaction involving a cyclization-1,2-migration cascade. The substrate scope was well studied and two possible mechanisms were suggested, involving either copper-coordinated allenic or alkynyl intermediates. No evidence in favor of either of the proposed mechanisms was provided.