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Intramolecular azide-alkene cycloaddition-elimination reaction in an aldohex-2-enonic acid derivative

Author:
Repetto, Evangelina, Oliveira Udry, Guillermo A., Varela, Oscar
Source:
Carbohydrate research 2019 v.483 pp. 107751
ISSN:
0008-6215
Subject:
aromatization, cycloaddition reactions, enzyme inhibitors, gluconolactone, p-toluenesulfonic acid, triazoles
Abstract:
A 6-azido-2-tosylenolate, obtained from D-glucono-1,5-lactone in six steps, underwent an intramolecular cycloaddition–elimination pathway under mild conditions, yielding a chiral, substituted 5,6-dihydro-4H-pyrrolo[1,2-c]-1,2,3-triazole. The conditions were optimized to give exclusive formation of the triazole. The mechanism appears to involve intramolecular ring closure via a 1,3-dipolar azide–alkene cycloaddition to give a 1,2,3-triazoline, followed by elimination of p-toluenesulfonic acid, leading to aromatization. Triazole products, obtained by chemical modification, are expected to display activity as enzyme inhibitors. Furthermore, partially protected derivatives of the 2-hexenoate were prepared as useful synthetic intermediates.
Agid:
6552182