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Development of Triazinone-Based Condensing Reagents for Amide Formation
Kohei Yamada1, Mika Kota1, Kensuke Takahashi1
1Faculty of Pharmaceutical Sciences , Institute of Medical, Pharmaceutical, and Health Sciences Kanazawa University , Kakuma-machi , Kanazawa 920-1192 , Japan.
Abstract:
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.
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