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Paper | Special issue | Vol 103, No. 2, 2021, pp.790-808
Published online, 27th November, 2020
DOI: 10.3987/COM-20-S(K)39
Intramolecular Transamidation-Cyclization of N-(α-Oxoacetyl) Diamine: Influence of Solvent, Acidity and Substituents

Takashi Kouko, Hiroaki Miyazawa, Hideki Hikita, Hiromi Totsuka, Kazuhiro Higuchi,* and Tomomi Kawasaki*

*Meiji Pharmaceutical University, 2-522-1 Noshio, Kiyose, Tokyo 204-8588, Japan

Abstract

We studied the selective formation of 3,5- and 2,5-pyrazinone via a transamidation-cyclization reaction. The equilibrium between acyl amides changed depending on the solvent, acidity, and substituents. Furthermore, selective transformation of 2,5-pyrazinone was accomplished by using a substrate with a secondary amine.