Studies on the mechanism of 1, 2-dihydropyrazin-2-one ring formation from dipeptidyl chloromethyl ketone and its chemical properties: Immediate deamination during …

A Miyazaki, Y Fujisawa, K Shiotani, Y Fujita…

Index: Miyazaki, Anna; Fujisawa, Yutaka; Shiotani, Kimitaka; Fujita, Yoshio; Li, Tingyou; Tsuda, Yuko; Yokoi, Toshio; Bryant, Sharon D.; Lazarus, Lawrence H.; Okada, Yoshio Chemical and Pharmaceutical Bulletin, 2005 , vol. 53, # 9 p. 1152 - 1158

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Citation Number: 2

Abstract

1, 2-Dihydropyrazin-2-one derivatives, which have two aminoalkyl groups at the positions 3 and 6, were found to be efficient tools for the construction of potent, selective and long-acting opioid mimetics. During the course of preparation, we found that the catalytic hydrogenation of 3, 6-bis (benzyloxycarbonylaminomethyl)-5-methyl-1, 2-dihydropyrazin-2-one to remove the benzyloxycarbonyl groups resulted in a side reaction. By MS and NMR studies and by ...