PHOTOCHEMICAL OXYGENATION OF PHENOLS BY PYRIMIDO[5,4-G]PTERIDINE N-OXIDE - COMPARATIVE-STUDIES WITH PYRIDAZINE AND ISOALLOXAZINE N-OXIDES

被引：10

作者：

SAKO, M ^{[1
]}

OHARA, S ^{[1
]}

HIROTA, K ^{[1
]}

MAKI, Y ^{[1
]}

机构：

[1] GIFU PHARMACEUT UNIV,6-1 MITAHORA HIGASHI 5-CHOME,GIFU 502,JAPAN

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 1990年 / 12期

关键词：

D O I：

10.1039/p19900003339

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

1,3,7,9-Tetrabutylpyrimido[5,4-g]pteridine-2,4,6,8(1H,3H,7H,9H)-tetraone 5-oxide 1 transfers its N-oxide oxygen to phenols, i.e., phenol 5, p-cresol 6, L-tyrosine methyl ester 7, and p-hydroxyacetanilide (acetaminophen) 8, under photochemical and conditions to give the corresponding dihydric phenols as major products without any accompanying photochemical intramolecular rearrangements of the N-oxide group taking place. This oxygenation is reasonably explained in terms of a photo-induced single-electron transfer (SET) followed by oxygen-atom transfer (the SET mechanism) which occurs via the initial formation of a charge-transfer complex between compound 1 and the phenols employed. Comparative experiments with 3,10-dibutylisoalloxazine 5-oxide 3 and 3-methylpyridazine 2-oxide 4 well demonstrate the simplicity and the mechanistic characteristics of the photochemistry of compound 1.

引用

页码：3339 / 3344

页数：6