Synthesis of thieno[2',3'(3',4' or 3',2'):5,6] azepino[2,1-alpha]isoindolediones from N-thienyl-2(3)-ylmethylphthalimides

Reduction of N-thienylmethylphthalimides 5a-e followed by the Wittig reaction gave the substituted acetic acids 8a-e. Their corresponding acyl chlorides where cyclized in the presence of aluminium trichloride to furnish the cyclic ketones 9a-e. Treatment of these ketones with bromine followed by triethylamine, or with selenium dioxide led to the thienoazepinoisoindolediones 1a-e.