Abstract Attempting some new approaches to 5, 11-dihyro-6H-pyrido [2, 3-b][1, 4] benzodiazepin-6-one (6), compounds 8, 10 and 11 were prepared. Ring enlargement of 4 into 6 failed, as well as condensation of 10 and 11 into ID, which is the potential precursor of pirenzepin (11-[2′-(4 ″-methylpiperazin-1 ″-yl)] acetyl derivative of 6) via an envisaged intramolecular Diels-Alder reaction. Model compounds 5 and 13 were prepared and their ...