Michael Edward Derieg

The reaction of epoxides with 1,4-benzodiazepines, mechanism and structural assignments

Abstract The reaction of epoxides with the imine moiety of 1,3-dihydro-2 H -1,4-benzodiazepin-2-ones yields oxazolo[3.2-d][1.4]-benzodiazepin-6-(7 H )-ones. A SN-2 initiated two-step mechanism is proposed. The reaction of propylene oxide with 7-chloro-1,3-dihydro-5-phenyl-2 H -1,4-benzodiazepin-2-one affords a mixture of epimers which are resolved and to which structures are assigned.

Quinazolines and 1,4-benzodiazepines. Part XXXVIII. The reaction of hydrazines with 6-chloro-2-chloromethyl-4-phenylquinazoline 3-oxide

The reactions of hydrazines with 6-chloro-2-chloromethyl-4-phenylquinazoline 3-oxide have been investigated. In the case of hydrazine, a benzodiazepine was obtained, and some of its reactions with acetylating agents are discussed. When 1,1-dimethylhydrazine and methylhydrazine were used, quinazoline hydrazones were obtained. A mechanism is suggested.