Issue 93, 2016, Issue in Progress

New method for in situ generation of enolate-iminium 1,4-dipoles for [4 + 2] and [4 + 1] dipolar heterocycloaddition reactions

Abstract

Generation of hydrazoylketenes by thermal decomposition of N-(diphenylenamino)pyrrolediones is accompanied by 5-exo-trig ring closure to furnish a zwitterionic dihydropyrazolone species. In contrast to Lisowskaya's earlier report, we established that in most cycloaddition reactions such dihydropyrazolones react as 1,4-dipoles. This reactivity pattern was demonstrated in several [4 + 4]-homodimerizations and in a series of [4 + 2] and [4 + 1] cycloaddition reactions with various dipolarophiles.

Graphical abstract: New method for in situ generation of enolate-iminium 1,4-dipoles for [4 + 2] and [4 + 1] dipolar heterocycloaddition reactions

Supplementary files

Article information

Article type
Paper
Submitted
01 Sep 2016
Accepted
12 Sep 2016
First published
14 Sep 2016

RSC Adv., 2016,6, 90239-90247

New method for in situ generation of enolate-iminium 1,4-dipoles for [4 + 2] and [4 + 1] dipolar heterocycloaddition reactions

V. E. Zhulanov, M. V. Dmitriev, A. N. Maslivets and M. Rubin, RSC Adv., 2016, 6, 90239 DOI: 10.1039/C6RA21981K

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