Beilstein J. Org. Chem.2016,12, 1897–1903, doi:10.3762/bjoc.12.179
University, 1-1-3 Minatojima Chuo-ku, Kobe 655-8586, Japan 10.3762/bjoc.12.179 Abstract This study describes the synthesis of triazine-based dehydrocondensing reagents substituted by amido substituents and demonstrates their efficiency for dehydrocondensingreactions in MeOH and THF. N-Phenylbenzamido
-substituted chlorotriazine is readily converted to a stable, non-hygroscopic triazinylammonium-based dehydrocondensing reagent that is superior to 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMT-MM) in terms of its reactivity in dehydrocondensingreactions.
Keywords: amide-forming
reactions; amido substituents; dehydrocondensingreactions; Fischer-type esterification; triazines; Introduction
We previously reported that dehydrocondensingreactions between carboxylic acids 1 and amines 2 to give amides 3 efficiently proceed in water or alcohols in the presence of the dehydrocondensing
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Graphical Abstract
Scheme 1:
Dehydrocondensing reactions using DMT-MM or DMT-Am, and a catalytic amide-forming reaction.