| Co-Investigator(Kenkyū-buntansha) |
TSUTSUMI Nozomi Showa University, School of Pharmaceutical Sciences, Assistant, 薬学部, 助手 (00255382)
MIYAZAKI Michiko Showa University, School of Pharmaceutical Sciences, Assistant, 薬学部, 助手 (00266165)
MATSUYA Yuji Showa University, School of Pharmaceutical Sciences, Assistant, 薬学部, 助手 (50255858)
NAGATA Kazuhiro Showa University, School of Pharmaceutical Sciences, Lecturer, 薬学部, 講師 (20208010)
ITOH Takashi Showa University, School of Pharmaceutical Sciences, Associate Professor, 薬学部, 助教授 (40159885)
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| Research Abstract |
Since last year, we have been investigating the synthetic method for 1,2,3,4-tetrazines and their benzo derivatives. In order to evaluate the scope and limitation of our reaction system. N-aminopyrazoles were oxidized byy various oxidizing agents to give N-nitrene derivatives, which were rearranged to corresponding 1,2,3-triazines. Since this reaction system was revealed to be effective for diverse 1,2,3-triazine derivatives, we applied the reaction to the oxidation of N-amino-l, 2,3-triazole. Thus, the oxidation of 1-amino-triazolotriazole afforded the triazolo-l, 2,3,4-tetrazine, which is the first aromatic tetrazine derivative. The reaction was thought to be of practical use because there are many triazole derivatives which are readily available. The other tetrazine derivatives were, however, not obtained by this procedure. The cause of this failure was studied using the molecular orbital calculations, and the results showed that 1,2,3,4-tetrazine would be decomposed via stepwise radical processes rather than concerted ones, thus the compound would be stable if it was synthesized Thus we decided to study another oxidizing agents to react with N-amino compounds, and found that nitric oxide, which has attracted much attention as a biological radical to act as diverse physiological signal transmitters, reacted with amino compounds in various manners depending upon the amount of molecular oxygen vs. NO.
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