Issue 40, 2018, Issue in Progress

Imido-substituted triazines as dehydrative condensing reagents for the chemoselective formation of amides in the presence of free hydroxy groups

Abstract

In this paper, we discuss the synthesis of imido-substituted chlorotriazines and demonstrate their use in dehydrative condensation reactions. Chemoselective amide-forming reactions of amino alcohols using succinimido-substituted chlorotriazine (2A) proceeded smoothly. Occasionally, nonselectivity was problematic during the synthesis of hydroxy-substituted amides. Moreover, it was noteworthy that this method was applicable to hydroxy-substituted carboxylic acids that could have formed a lactone or an ester during the carboxylic acid activation step. The imido-substituted chlorotriazine (2A) was superior to the amido-substituted chlorotriazine and 2-chloro-4,6-dimethoxy-1,3,5-triazine (CDMT) in terms of reaction rates and yields.

Graphical abstract: Imido-substituted triazines as dehydrative condensing reagents for the chemoselective formation of amides in the presence of free hydroxy groups

Supplementary files

Article information

Article type
Paper
Submitted
10 Apr 2018
Accepted
13 Jun 2018
First published
20 Jun 2018
This article is Open Access
Creative Commons BY-NC license

RSC Adv., 2018,8, 22482-22489

Imido-substituted triazines as dehydrative condensing reagents for the chemoselective formation of amides in the presence of free hydroxy groups

M. Kitamura, S. Sasaki, R. Nishikawa, K. Yamada and M. Kunishima, RSC Adv., 2018, 8, 22482 DOI: 10.1039/C8RA03057J

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