Latent Enamine Functionality of 5-Methyl-2,3-dihydropyrazines
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概要
- 論文の詳細を見る
Tautomerization of methyl-substituted dihydropyrazine (DHP) derivatives to their latent enamine form was investigated theoretically and empirically. Among two types of hydrogen transfer model simulated by means of density functional theory calculation, a simple intramolecular hydrogen shift mechanism for 5,6-dimethyl-2,3-dihydropyrazine (1) and 5-methyl-6-phenyl-2,3-dihydropyrazine (3) required high activation energies for tautomerism, while a water-assisted intermolecular hydrogen transfer mechanism gave smaller activation energies (about 160 kJ/mol). Examination of the deuterium exchange reaction of 3 in 50% (v/v) D2O/dimethyl sulfoxide-d6 solution revealed temperature-dependent and stepwise deuterium exchange of the 5-methyl group. Reaction of compound 3 with phenyl isocyanate in acetonitrile afforded a mono adduct (7) at the 5-methyl group, and a cyclic adduct (8). These results represent evidence of tautomerism of 5-methyl-2,3-dihydropyrazines (imine forms) to the latent enamine tautomers, and suggest that DHPs may behave as enamines to a significant degree under physiological conditions.
著者
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KAGECHIKA Hiroyuki
Graduate School of Pharmaceutical Sciences, The University of Tokyo
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Kagechika Hiroyuki
Graduate School Of Biomedical Sci. Tokyo Medical And Dental Univ.
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HIRANO Tomoya
Institute for Materials Research, Tohoku University
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TAKECHI Shinji
Faculty of Pharmaceutical Sciences, Sojo University
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ITO Shigeru
Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University
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YAMAGUCHI Tadatoshi
Faculty of Pharmaceutical Sciences, Sojo University
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SUGIMOTO Akiko
Institute of Biomaterials and Bioengineering, Tokyo Medical and Dental University
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Ito S
Institute For Medical And Dental Engineering Tokyo Medical And Dental University
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Hirano Tomoya
Institute For Materials Research Tohoku University
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Sugimoto Akiko
Institute For Medical And Dental Engineering Tokyo Medical And Dental University
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Takechi Shinji
Faculty Of Pharmaceutical Sciences Sojo University
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Yamaguchi Tadatoshi
Faculty Of Pharmaceutical Sciences Sojo University
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Ito Shigeru
Institute For Medical And Dental Engineering Tokyo Medical And Dental University
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Kagechika Hiroyuki
Graduate School of Biomedical Science, Tokyo Medical and Dental University
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Takechi Shinji
Faculty of Pharmaceutical Science, Sojo University
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Yamaguchi Tadatoshi
Faculty of Pharmaceutical Science, Sojo University
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