Trizaine-based dehydrative condensation reagents bearing carbon-substituents

Herein, we report on the synthesis of alkyl-, aryl-, and alkynyl-substituted chlorotriazines and their ammonium salts, and demonstrate their utility in dehydrative condensation reactions. Although the electrophilicity of these reagents is mainly dependent on the hybridization of the carbon-substituents, it was found that bulky 2,6-dimethylphenyl group-substituted reagents resulted in the highest product yields because of a slight increase in reagent electrophilicity and/or steric hindrance favorable for desired dehydrative condensation reactions. [Display omitted] •Amide-forming reactions with triazines bearing carbon-substituents proceed smoothly even in the absence of oxygen- or nitrogen-containing subsutituents.•Electrophilicity of these reagents is mainly dependent on the hybridization of the carbon-substituents.•Bulky 2,6-dimethylphenyl group-substituted reagents resulted in the highest product yields because of a slight increase in reagent electrophilicity and/or steric hindrance favorable for desired dehydrative condensation reactions.