DOI: https://doi.org/10.15421/081304
Cover Image

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

Aleksandr A. Gaponov

Abstract


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.  

Keywords


1,5-dihydrobenzodiazepinone-2; alkylation; quaternization

References


Andronati, S. A. Meditsinskaya himiya. Struktura, svoystva, molekulyarnyie mehanizmyi deystviya biologicheski aktivnyih veschestv, Odessa: Astroprint, 2006, 132 p.

Bogatskiy, A.V., Andronati, S.A., Golovenko, N.Ya. Trankvilizatoryi. 1,4-Benzodiazepinyi i rodstvennyie strukturyi, Kiev, 1980, 280 p.

Gaponov, A. A. Reaction of 2,3-dihydro-1H-1,5-2-benzodiazepinonov with alkylating agents. Visn. Dnipropetr. Univ.: Khim., 2010, no. 16, p. 99-104.

Vernin, D., Domloi, H., Siv, C., Metzger, J., Archavlis, A., Llinas, J. R. Alkylation en catalyse par transfert de phase de dihydro-1,3-(2H)benzo[2,3-b]diazepines-1,5-ones-2. Chem. Scripta, 1980, no. 16, p. 157-162.

Bellami, L. Infrakrasnyie spectryi slognuch molekul, Moscow: IL, 1963, 592 p.

Nakanisi, K. Infrakrasnyie spectryi i stroenie organicheskich soedinenij, Moscow: Mir, 1965, 216 p.


Comments on this article

View all comments




Creative Commons License
This work is licensed under a Creative Commons Attribution 4.0 International License.

______________________________________________________
Journal of Chemistry and Technologies
eISSN: | pISSN:
Address of founder:chem.dnu@gmail.com
The journal publishes scientific works on conditions: Creative Commons Attribution 4.0 International License
Founder: Oles Honchar Dnipro National University