posted on 2019-11-08, 02:30authored byKohei Yamada, Mika Kota, Kensuke Takahashi, Hikaru Fujita, Masanori Kitamura, Munetaka Kunishima
Novel
triazinone-based condensing reagents have been developed.
The palladium-catalyzed O–N allylic rearrangement of 2-(allyloxy)-4,6-dichloro-1,3,5-triazine
and subsequent regioselective substitution using alcohols and an amine
afforded chlorotriazinones, which can be readily converted using N-methylmorpholine into the corresponding condensing reagents.
The condensation of carboxylic acids and amines using these reagents
proceeded to afford the desired amides in good yields. In comparison
with 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride,
the newly synthesized triazinone-based condensing reagents exhibited
higher reactivity.