Synthesis of Dibenzo [b, f] cycloprop [d] azepine Derivatives. I. Introduction of a Cyclopropane Ring by the Use of Simmons-Smith Reagent

Abstract

The Simmons-Smith reaction of 5H-dibenz [b, f] azepine (4) and 5-methyl-5H-dibenz-[b, f] azepine (5) yielded 1, 1a, 6, 10b-tetrahydro-6-methyldibenzo [b, f] cycloprop [d] azepine (6), which represents synthesis of a novel condensed ring system. 6 was demethylated via the formamide derivative 7 to give 1, 1a, 6, 10b-tetrahydrodibenzo [b, f] cycloprop [d]-azepine (8), which was converted into pharmacologically active 6-dialkylaminoalkyl (9) and 6-carbamoyl (17) derivatives. Cyclopropanation of 5-(3-halopropyl)-5H-dibenz [b, f] azepines (11) with the Simmons-Smith reagent, however, led to additional reactions in the side chain to yield 12, 13, 14, and 15.