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Reactions of 2,3-dihydro-1,5-benzodiazepinones-2 derivatives quaternization

Aleksandr A. Gaponov


Alkylation of 1-alkyl-4-methyl-2,3-dihydro-1,5-benzodiazepinones-2 with alkyl halides is shown to result in the formation of quaternary salts. In contrast to 1,5-benzodiazepinones-2, unsubstituted at position 1, quaternization of 1-alkyl-derivatives requires larger excess of alkyl halide and prolonged (18-46 h) boiling in benzene. Quaternary salts are obtained in yields 45-77% as crystalline deposits or oils which crystallized upon grinding with ether or hexane. The yields depended on the nature of alkyl halide and the substituent at position 4. The yields obtained with ethyl iodide were notably lower compared to those with methyl iodide, and the reactions were significantly slower. At the same time, quaternization of 1-alkyl-4-phenyl-2,3-dihydro-1,5-benzodiazepinones-2 did not proceed even upon boiling in benzene with methyl iodide for 80 h.  


1,5-dihydrobenzodiazepinone-2; alkylation; quaternization


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