Synthesis of dipyrazolo[3,4-b : 4′,3′-f]azepines and dithieno[2,3-b : 3′,2′f]azepines from 1-substituted 2,7-dichloro-4,5-dihydro-1H-azepine-3,6-dicarbaldehydes

Abstract

Syntheses of the title compounds (7) and (8) are described. These new bis-heterocyclic analogues of dibenzo[b,f]azepines (4) were readily obtained from the di-β-chlorovinyl aldehydes (3), the latter prepared by formylation of the azepines (5). The thiophene analogue (10) of the antidepressant ‘imipramine’ was then synthesized by debenzylation of the dithienoazepine (8a) followed by condensation with an appropriate halide.