N-ヘテロ芳香族の電子的性状(第21報) : υ-Triazolo[d]pyrimidine誘導体のポーラログラフィー的挙動

概要

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Polarographic behavior of υ-triazolo[d]pyrimidine (I) and its 5-amino (II), 7-amino (III), 5,7-diamino (IV), 7-amino-5-hydroxy (V), 5-amino-7-hydroxy (VI), 5,7-dihydroxy (VII), and 7-hydroxy (VIII) derivatives was investigated. Whereas compounds I-V were polarographically reducible, no reduction waves were obtained with compounds VI-VIII, indicating that substituents at 7-position have a dominant effect on reducibility. Substituents at 5-position had only a slight effect on reducibility. It was presumed from the substituent effect that the first step of reduction may take place at N_6-C_7 double bond of the pyrimidine moiety. It was revealed that triazolopyrimidine derivatives were more easily reduced at the dropping mercury electrode than the corresponding purine derivatives, which might be ascribable to the difference in tendencies of inflow of π-electrons into the pyrimidine ring moiety from the neighboring ring (imidazole or triazole). Parallel relationship was found between the easiness of reduction and energy levels of the lowest vacant orbitals, which have been computed by simple LCAO MO method.
公益社団法人日本薬学会の論文
1968-04-25