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Synfacts 2009(3): 0263-0263
DOI: 10.1055/s-0028-1087788
DOI: 10.1055/s-0028-1087788
Synthesis of Heterocycles
© Georg Thieme Verlag
Stuttgart ˙ New York
Three-Component Synthesis of Pyrido[2,1-a]isoindoles
C. Xie, Y. Zhang*, P. Xu
Hangzhou Normal University, P. R. of China
Further Information
Publication History
Publication Date:
19 February 2009 (online)
Significance
Reported is the synthesis of pyrido[2,1-a]isoindoles involving a three-component reaction of 2-bromoacetophenones, pyridines (or isoindoles) and 2-(trimethylsilyl)phenyltriflates. A plausible mechanism is proposed, whereby the pyridine and bromoacetophenone undergo reaction to form a stabilized 1,3-dipole which then undergoes a [3+2] cycloaddition with the in situ formed benzyne to give the heterocyclic product.