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Facile routes for the preparation of 3,4-disubstituted 1,3-oxazolidines and 1,2,5-trisubstituted imidazolidin-4-ones

✍ Scribed by Alessia Catalano; Alessia Carocci; Giovanni Lentini; Antonia Di Mola; Claudio Bruno; Carlo Franchini

Publisher
Journal of Heterocyclic Chemistry
Year
2010
Tongue
English
Weight
115 KB
Volume
48
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

Facile, alternative synthetic routes to 6, (R)‐6, and (S)‐6‐3‐benzyl‐N‐(2,6‐dimethylphenyl)‐1,3‐oxazolidine‐4‐carboxamides (6), a chiral oxazolidine derivative of tocainide, are reported. The synthetic routes described herein also afforded 11‐, (R)‐11‐, and 12, which present the imidazolidin‐4‐one core and belong to a class of compounds interesting for their biological activities. All the final compounds and intermediates were fully characterized. Enantiomeric excesses of homochiral 6 and 11 were determined by capillary electrophoresis analysis using 2‐hydroxypropyl‐β‐cyclodextrin or highly sulfated γ‐cyclodextrin as chiral selectors. J. Heterocyclic Chem., (2010)

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## Abstract The reaction of thiocarbohydrazide with carboxylic acids at the melting temperature allows an improved preparation of the S‐substituted 4‐amino‐3‐mercapto‐1,2,4‐triazole heterocycles. The crude 4‐amino‐5‐mercapto‐1,2,4‐triazoles react easily with carboxylic acids or carboxylic acid chlo