D. T. T. Nguyen, H. H. Truong, N. T. Dao, V. T. T. Tran, O. S. Gorchakova, A. T. Le, “Unexpected hydrazine- and hydroxylamine-induced transformations of aza-14-crown-4 incorporating 4-oxopiperidine-3-carboxylate moiety”, Mendeleev Commun., 2023, Volume 33, Issue 5,Pages <nobr>708

This article is cited in 1 paper

Communications

Unexpected hydrazine- and hydroxylamine-induced transformations of aza-14-crown-4 incorporating 4-oxopiperidine-3-carboxylate moiety

D. T. T. Nguyen^a, H. H. Truong^b, N. T. Dao^a, V. T. T. Tran^a, O. S. Gorchakova^c, A. T. Le^a

^a Faculty of Chemistry, University of Science, Vietnam National University, Hanoi, Hoan Kiem, Hanoi, Vietnam
^b Peoples Friendship University of Russia (RUDN University), Moscow, Russian Federation
^c 'Sanofi-aventis group' Representative office in Russia, Moscow, Russian Federation

Abstract: Reactions of aza-14-crown-4 incorporating 4-oxopiperidine-3-carboxylate moiety with hydrazine and hydroxylamine proceed at the functional groups. One unexpected product, cyclopenteno-13-crown-3 ether derivative, is formed when hydrazine hydrochloride is used, its formation occurring via deamination of the piperidine followed by the Nazarov reaction of the intermediate hydrazono diene. According to the QSAR through ADMET calculation, the synthesized compounds may show high potential for biological studies.

Keywords: azacrown ether, piperidone, Nazarov reaction, hydrazone, cyclopenteno-13-crown-3 ether.

Language: English

DOI: 10.1016/j.mencom.2023.09.037

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