The singlet oxygen oxidation of chlorpromazine and some phenothiazine derivatives. Products and reaction mechanisms

被引：20

作者：

Baciocchi, Enrico

Del Giacco, Tiziana

Lanzalunga, Osvaldo

Lapi, Andrea

Raponi, Daniele

机构：

[1] Univ Roma La Sapienza, Ist CNR Metodol Chim, IMC, Sez Meccanismi Reaz, I-00185 Rome, Italy

[2] Univ Roma La Sapienza, Dipartimento Chim, I-00185 Rome, Italy

[3] Univ Perugia, Dipartimento Chim, I-06123 Perugia, Italy

[4] Univ Perugia, Ctr Eccellenza Mat Innovat Nanostrutturati, I-06123 Perugia, Italy

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2007年 / 72卷 / 15期

关键词：

D O I：

10.1021/jo0706980

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A kinetic and product study of the reactions of chlorpromazine 1, N-methylphenothiazine 2, and N-ethylphenothiazine 3 with singlet oxygen was carried out in MeOH and MeCN. 1 undergoes exclusive side-chain cleavage, whereas the reactions of 2 and 3, in MeOH, afforded only the corresponding sulfoxides. A mechanism for the reaction of 1 is proposed where the first step involves an interaction between singlet oxygen and the side-chain dimethylamino nitrogen. This explains why no side-chain cleavage is observed for 2 and 3.

引用

页码：5912 / 5915

页数：4

共 31 条

[1] MECHANISM OF PRODUCTION OF SINGLET OXYGEN ON PHOTOEXCITATION OF DRUGS INDUCING PHOTOSENSITIVITY [J].