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Synthesis of thieno[2,3‐c]pyridines and related heterocyclic systems

1993; Wiley; Volume: 57; Issue: 1 Linguagem: Inglês

10.1002/jctb.280570104

1097-4660

Hussein El‐Kashef, Ahmed A. Geies, Adel M. Kamal El‐Dean, A. A. ABDEL‐HAFEZ,

Synthesis and biological activity

Abstract 1‐Isopropyl‐4‐piperidone (1) reacts with sulphur and active methylene nitriles to give thienopyridines (2a‐c). Compounds 2a, b react with CS 2 in pyridine to produce pyridothienopyrimidines (3a, b) which upon methylation with MeI give S‐methylated derivatives (4a, b). Dibenzylidene compound (5) reacts with hydrazine hydrate, phenyl hydrazine, thiourea malononitrile or cyanoacetamide to give compounds 6–9 respectively. Piperidylidene malononitrile (10) reacts with benzaldehyde to give derivative 11 which undergoes an addition reaction with malononitrile to give 12 which is also obtained by reacting 1 with one mole of benzaldehyde and two moles of malononitrile.