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Synthesis 2012(6): 865-874  
DOI: 10.1055/s-0031-1289720
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Construction of Novel Tricyclic Fused-Ring Systems by the Multicomponent Reactions of Imidazo[1,5-a]pyridine Carbenes with Aromatic ortho-Dialde­hydes and Electron-Deficient Alkynes

Cai-Xia Yan, Zhong-Xin Sun, Ying Cheng*
College of Chemistry, Beijing Normal University, Beijing 100875, P. R. of China
Fax: +86(10)58805558; e-Mail: ycheng2@bnu.edu.cn;
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Publication History

Received 4 November 2011
Publication Date:
17 February 2012 (online)

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Abstract

The multicomponent reactions of imidazo[1,5-a]pyridine carbenes with heterocyclic ortho-dialdehydes and electron-deficient­ alkynes were studied. While imidazo[1,5-a]pyridin-3-ylidenes reacted with furan-3,4-dicarbaldehyde and dimethyl acetylenedicarboxylate or dibenzoylacetylene to produce multifunctional difuro[3,2-b:3′,4′-d]azepines, the reaction of imidazo[1,5-a]pyridin-3-ylidenes with thiophene-3,4-dicarbaldehyde and activated alkynes afforded furo[3,2-b]thieno[3,4-d]azepine derivatives. This work not only provides two new types of tricyclic fused azepines, but also extends the applications of multicomponent reactions of N-heterocyclic carbenes in the construction of complicated fused-ring systems.

Key words

multicomponent reactions - carbenes - fused-ring systems - difuro[3,2-b:3′,4′-d]azepines - furo[3,2-b]thieno[3,4-d]azepines

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CCDC 861017 (8a) contains the supplementary crystallographic data for this paper. Copies of these data can be obtained, free of charge, from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.