Interaction of 2,3-dihydro-1H-benzodiazepinone-2 with epichlorhydrine

Authors

  • Oleksandr O. Gaponov Oles Honchar Dnipropetrovsk National University, 72, Gagarin Ave., Dnipropetrovsk 49010, Ukraine
  • Igor N. Tarabara Oles Honchar Dnipropetrovsk National University, 72, Gagarin Ave., Dnipropetrovsk 49010, Ukraine

DOI:

https://doi.org/10.15421/081401

Keywords:

1, 5-dihydrobenzodiazepinone-2, epichlorhydrine, structure

Abstract

Derivatives of 1,5-benzodiazepines show various pharmacological activity. The presence of several reactive centers predetermines the possibility of reactions of 1,5-benzodiazepines both with electrophilic and nucleophilic reagents of various types. In addition, these compounds are suitable objects for the synthesis of new tricyclic systems containing a diazepinic cycle. In the article, the interaction of 4-phenyl- and 4-methyl-2,3-dihydro-1Н-1,5-benzodiazepine-2-ones with epichlorhydrin under various conditions is reported. It has been shown that under strongly basic conditions the reactions proceed at the nitrogen atom N1 and N1-glycidyl-1,5- benzodiazepine-2-ones are obtained. The yields of products were 71-79%. Under soft basic conditions the reactions either did not proceed at all or were accompanied by the formation of side-products.

Author Biographies

Oleksandr O. Gaponov, Oles Honchar Dnipropetrovsk National University, 72, Gagarin Ave., Dnipropetrovsk 49010

Senior Research Chemist, Organic Chemistry Department, PhD in Organic Chemistry

Igor N. Tarabara, Oles Honchar Dnipropetrovsk National University, 72, Gagarin Ave., Dnipropetrovsk 49010

Associate Professor, Organic Chemistry Department, PhD in Organic Chemistry

References

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Gaponov, A. A. Reaction of 2,3-dihydro-1H-1,5-2-benzodiazepinonov with alkylating agents. Visn. Dnipropetr. Univ.: Khim., 2010, vol. 18, no. 16, p. 99–104. [in Russian]

Kost, A. N., Scharbatyan, P. A., Terent′yev, P. B., Solomko, Z. F., Tkachenko, V. S., Gergel, L. G. Mass-spektryi 1,5-benzodiazepinone-2. Zh. Org. Khim, 1972, vol. 8, no. 10, p. 2113–2119. [in Russian]

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Published

2014-12-02

Issue

Vol. 22 No. 1 (2014): Bulletin of Dnipropetrovsk University. Series Chemistry

Section

Organic Chemistry

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Copyright (c) 2014 Oles Honchar Dnipropetrovsk National University

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