Studies on the chemistry of thieno-anellated O,N- and S,N-containing heterocycles. 2. Synthesis of thieno[2,3-b]diazepine derivatives with potential CNS activity

Thieno-anellated compounds analogous to Clobazam (1) [2] and the nootropic drugs 2 and 3 [3] were synthesized. Thus, nucleophilic substitution on halogenated nitrothiophene derivatives with aniline and reaction with ethyl malonyl chloride gave after cyclisation the thieno[2,3-b]diazepinedione derivatives 7 and 14 . These compounds were methylated to give the thieno-anellated heterocycles 8 and 9 .