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Synfacts 2009(3): 0263-0263  
DOI: 10.1055/s-0028-1087788
Synthesis of Heterocycles
© Georg Thieme Verlag Stuttgart ˙ New York

Three-Component Synthesis of Pyrido[2,1-a]isoindoles

Contributor(s): Victor Snieckus, Johnathan Board
C. Xie, Y. Zhang*, P. Xu
Hangzhou Normal University, P. R. of China
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Publikationsverlauf

Publikationsdatum:
19. Februar 2009 (online)

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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.