Synthesis of tricyclic and tetracyclic thieno[3,2-f]-1,4-thiazepines

Article abstract of DOI:10.1002/jhet.5570340332

Treatment of 5-methylthio-2,3-dihydrothieno[3,2-f]-1,4-thiazepine (9) with acylhydrazines gave 5,6-dihydrothieno[3,2-f]-1,2,4-triazolo[4,3- d][1,4]thiazepines 10, 11, and that of 9 with ethyl anthranilate gave 5,6- dihydrothieno[3',2':6,7][1,4]thiazepino[5,4-b]quinazolin-8-one (14). Reaction of 9 with hydrazinc hydrate or 4-chlorophenylhydrazine afforded 5-hydrazino compounds 12, 15, which were subsequently cyclized to ethyl 5,6- dihydrothieno[3,2-f]-1,2,4-triazolo[4,3-d][1,4]thiazepine-3-carboxylate (13), 2-(4-chlorophenyl)-5,6-dihydrothieno[3,2-f]-1,2,4-triazolo[4,3- d][1,4]thiazepin-3(2H)-one (16) and 2-(4-chlorophenyl)-6,7-dihydro-2H- thieno[3,2-f][1,2,4]triazino[4,3-d][1,4]thiazepine-3,4-dione (17). New thieno-anellated heterocycles were prepared with the aim of studying their affinity for the benzodiazepine receptors.