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Short Paper | Regular issue | Vol 85, No. 3, 2012, pp.697-704
Published online, 10th February, 2012
DOI: 10.3987/COM-12-12422
A New Synthetic Approach to Azuleno[2,1-b]pyridin-4(1H)-ones

Dao-Lin Wang,* Qing-Tao Cui, Shan-Shan Feng, and Jia-Yi Yu

*Liaoning Key Laboratory of Synthesis and Application of Functional Compound, College of Chemistry & Chemical Engineering, Bohai University, Jinzhou 121001, China

Abstract

3-(Dimethylamino)-2-(2-methoxy-1-ethoxycarbonylazulen-3-oyl)acrylonitrile (4) as new synthons directed to heterocycle-fused azulene was obtained by the condensation of ethyl 1-cyanoacetyl-2-methoxyazulene-3-carboxylate (3) and N,N-dimethylformamide dimethyl acetal (DMFDMA). Reaction of this βenaminone with primary amines (5) in EtOH at fluxing then affords N-substituted 3-cyano-10-ethoxycarbonylazuleno[2,1-b]-pyridin-4(1H)-one derivatives (6) in good yields by a tandem addition-elimination-SNAr reaction. This reaction provides a new procedure for synthesis of pyridinone-fused azulenes.