Potent triazine-based dehydrocondensing reagents substituted by an amido group

• Munetaka Kunishima,
• Daiki Kato,
• Nobu Kimura,
• Masanori Kitamura,
• Kohei Yamada and
• Kazuhito Hioki

Beilstein J. Org. Chem. 2016, 12, 1897–1903, doi:10.3762/bjoc.12.179

• catalytic amide-forming reactions in water using triazinylammonium salts (DMT-Am) generated in situ from CDMT and a catalytic amount of tertiary amines 5 (Scheme 1d). Most notably, by introducing various functional groups into 5, it was possible to develop a cyclodextrin-based artificial acyltransferase [7

• substituent in place of the methoxy groups. To date, several triazine derivatives possessing phenoxy [15][16], 2,2,2-trifluoroethoxy [17], or N-ethylamino groups [18] in place of the methoxy groups have been prepared, and the reactivity of these compounds in amide-forming reactions has been examined. The

• evaluate the reactivity of these chlorotriazines in amide-forming reactions, one-pot reactions were performed (Table 1a), i.e., the chlorotriazines were added to a mixture of carboxylic acid 1a, amine 2a, and NMM in MeOH or THF at room temperature. The amide-forming reaction in the absence of NMM did not