Synfacts 2007(9): 0922-0922  
DOI: 10.1055/s-2007-968913
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart · New York

Rhodium-Catalyzed Synthesis of Indolizines and Imidazopyridines

Contributor(s): Victor Snieckus, Yigang Zhao
S. Chuprakov, F. W. Hwang, V. Gevorgyan*
University of Illinois at Chicago, USA
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Publication History

Publication Date:
23 August 2007 (online)


A Rh-catalyzed synthesis of indol­izines and imidazopyridines is described which involves an interesting reaction of alkynes and nitriles with pyridotriazoles with overall loss of nitrogen. A proposed mechanism involves the initial equilibration of the closed 1 and open 2 isomers of the pyridotriazole, followed by formation of the Rh-carbenoid species 3 and direct nucleophilic attack of an alkyne or nitrile to finally afford the indolizine and imidazopyridine derivatives. C7-substitution in the pyridotriazoles is required to drive the equilibrium to the open-ring form 2.