A NEW SYNTHETIC APPROACH TO AZULENO[2,1-b]PYRIDIN-4(1H)-ONES

[摘要]：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 beta-enaminone 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.

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