Issue 28, 2012

Click-chemistry approach to azacycloalkene monosulfonyl diamines: synthesis and computational analysis of the reaction mechanism

Abstract

The cycloaddition reaction of the morpholino enamines of N-methylpiperidone and N-methyl tropinone with sulfonylazides was exploited, leading to a click-chemistry approach to uncommon azacycloalkene monosulfonyl diamines in good yields. A computational model for the key step decomposition of the triazoline intermediate was then realized by DFT calculations. The model explains the observed reaction outcome and leads to a new interpretation of the decomposition mechanism for 5-amino-1,2,3-triazolines.

Graphical abstract: Click-chemistry approach to azacycloalkene monosulfonyl diamines: synthesis and computational analysis of the reaction mechanism

Supplementary files

Article information

Article type
Paper
Submitted
27 Jul 2012
Accepted
07 Sep 2012
First published
11 Sep 2012

RSC Adv., 2012,2, 10652-10660

Click-chemistry approach to azacycloalkene monosulfonyl diamines: synthesis and computational analysis of the reaction mechanism

A. Contini and E. Erba, RSC Adv., 2012, 2, 10652 DOI: 10.1039/C2RA21592F

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