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The reaction of cyanoacetanilide derivative  1  with some electrophiles was investigated. Treatment of compound  1  with 2-(2-oxoindol-3-ylidene)malononitrile ( 2a ) under reflux in ethanol in the presence of piperidine afforded the spiro[indoline-3,4′-pyridine] derivative  3 . Under similar conditions, condensation of compound  1  with the analog  2b  yielded a spiroindole  4 . Chromeno[3,4- c ]pyridine derivative  6  was obtained by cyclization of chromene derivative  5  with ethyl cyanoacetate. In a similar manner, condensation of compound  5  with cylcohexanone under reflux in ethanol in the presence of sodium acetate furnished chromeno[3,4- c ]quinoline derivative  7 . Compound  1  was condensed with 2-hydroxy-1-naphthaldehyde to yield the benzo[ f ]chromeno derivative  8 . Refluxing of benzochromene derivative  8  with ethyl cyanoacetate in ethanol in the presence of catalytic amount of piperidine produced benzo[ f ]chromeno[3,4- c ]pyridine derivative  9 . The structures of the newly synthesized compounds were confirmed on the basis of analytical and spectral data.

heterocyclic communications

Cyanoacetanilide intermediates in heterocyclic synthesis. Part 7: preparation of some spiro[indoline-3,4′-pyridine] and chromeno[3,4-c]pyridine derivatives