A Caveat on the Use of 2-Chloro-4,6-dimethoxy-1,3,5-triazine for the Synthesis of 4,4-Dimethyl-2-R-2-Oxazolines

Robert   A.   Gossage; Amber   L.   Sadowy

doi:10.2174/1570178053400018

Abstract

The reported synthesis of 4,4-dimethyl-2-R-2-oxazolines from carboxylic acids and 2-amino-2- methyl-1-propanol (1) using 2-chloro-4,6-dimethoxy-1,3,5-triazine (2) via direct coupling / cyclisation is questioned. The results reported herein indicate that the products are actually ?-hydroxyamides resulting from dehydrative R-COOH / 1 (peptide) coupling only, which has been known to be mediated by 2 for some time.

Keywords: oxazoline, triazine, coupling reactions, amides, amino alcohols, 4,5-dihydro-2-oxazole

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Letters in Organic Chemistry

Title: A Caveat on the Use of 2-Chloro-4,6-dimethoxy-1,3,5-triazine for the Synthesis of 4,4-Dimethyl-2-R-2-Oxazolines

Volume: 2 Issue: 1

Author(s): Robert A. Gossage and Amber L. Sadowy

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Keywords: oxazoline, triazine, coupling reactions, amides, amino alcohols, 4,5-dihydro-2-oxazole

Abstract: The reported synthesis of 4,4-dimethyl-2-R-2-oxazolines from carboxylic acids and 2-amino-2- methyl-1-propanol (1) using 2-chloro-4,6-dimethoxy-1,3,5-triazine (2) via direct coupling / cyclisation is questioned. The results reported herein indicate that the products are actually ?-hydroxyamides resulting from dehydrative R-COOH / 1 (peptide) coupling only, which has been known to be mediated by 2 for some time.

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Gossage A. Robert and Sadowy L. Amber, A Caveat on the Use of 2-Chloro-4,6-dimethoxy-1,3,5-triazine for the Synthesis of 4,4-Dimethyl-2-R-2-Oxazolines, Letters in Organic Chemistry 2005; 2 (1) . https://dx.doi.org/10.2174/1570178053400018