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Paper | Special issue | Vol 97, No. 1, 2018, pp.253-259
Published online, 26th January, 2018
DOI: 10.3987/COM-17-S(T)14
Activation of 1-Methyl-5-nitro-2-pyrimidinone by Dearomatization Using a Secondary Amine

Haruyasu Asahara, Azusa Yasuoka, and Nagatoshi Nishiwaki*

*School of Environmental Science and Engineering, Kochi University of Technology, Tosayamada-cho, Kami, Kochi, 782-8502, Japan

Abstract

Electron-deficient 1-methyl-5-nitro-2-pyrimidinone is easily attacked by methanol or pyrrolidine to afford the corresponding adducts, respectively, by which aromaticity of nitropyrimidinone is lost. Indeed, the amine-adduct exhibited higher reactivity than that of original structure to facilitate the reaction with 1,3-dicarbonyl compound leading to diazabicyclic compound at room temperature. The amine-adduct also underwent the ring opening reaction to furnish nitroenamines with (Z)-configuration.