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■ Reactivity of the Enamine Tautomer of a Cyclic 1,4-Diazadiene with a Diketone

Kazuhide Nakahara,* Koki Yamaguchi, and Hisao Kansui

*Department of Integrative Pharmaceutical Sciences, Faculty of Pharmaceutical Sciences, Setsunan University, 45-1, Nagaotoge-cho, Hirakata-shi, Osaka 573-0101, Japan

Abstract

Cyclic 1,4-diazadiene (2,3-dihydro-5-methyl-6-phenylpyrazine) and diketone (1-phenyl-1,2-propanedione) yielded two products via dehydration–condensation of the diamine and diketone moieties when a mixture of H2O and MeOH was used as the solvent. The structures of the new products were established by 2D NMR analysis. Single-crystal X-ray structural characterization and density functional theory calculations allowed us to determine that this reaction took place via reaction of the enamine tautomer.