3-ACYL-1,5-BENZODIAZEPINES IN THE REACTIONS OF 5,5-DIMETHYL-2-FORMYLCYCLOHEXANE-1,3-DIONE WITH CERTAIN 1,2-DIAMINOBENZENES

Abstract

Reaction of 5,5-dimethyl-2-formylcyclohexane-1,3-dione with 4-methyl-, 4-benzoyl-, and 4-nitro-1,2-diaminobenzenes gave the corresponding 2-(2-amino-4-methylphenylaminomethylene)-, 2-(2-amino-5-benzoylphenylaminomethylene)-, and 2-(2-amino-5-nitrophenylaminomethylene)-5,5-dimethylcyclohexane-1,3-diones. When treated with hydrochloric acid, they cyclize to 7-methyl-, 8-benzoyl-, and 8-nitro-3,3-dimethyl-2,3,4,5-tetrahydro-1H-dibenzo[b,e][1,4]diazepinone hydrochlorides. Under hydrolytic conditions the salts of 3,3,7-trimethyl-2,3,4,5-tetrahydro-1H-dibenzo[b,e][1,4]diazepinone and 3,3-dimethyl-2,3,4,5-tetrahydro-1H-dibenzo[b,e][1,4]diazepinone undergo the C11–N10 bond cleavage to give N-(2-aminophenyl)- and N-(2-amino-5-methylphenyl)-substituted 3-amino-2-formyl-5,5-dimethylcyclohex-2-enones. Ring opening of the hydrochlorides of 8-benzoyl-, and 3,3-dimethyl-8-nitro-2,3,4,5-tetrahydro-1H-dibenzo[b,e]-[1,4]diazepinones occurs at the C–N5 bond and gives the starting enamines.

Authors: A. I. Gurkovskii, N. N. Tonkikh, M. V. Petrova, and A. Ya. Strakov.

English Translation in Chemistry of Heterocyclic Compounds, 1999, 35 (5), pp 625-629

http://link.springer.com/article/10.1007/BF02324651