The Singlet Oxygen Oxidation of Chlorpromazine and Some Phenothiazine Derivatives. Products and Reaction Mechanisms

详细信息    查看全文

• 作者：Enrico Baciocchi ; Tiziana Del Giacco ; Osvaldo Lanzalunga ; Andrea Lapi ; Daniele Raponi
• 刊名：Journal of Organic Chemistry
• 出版年：2007
• 出版时间：July 20, 2007
• 年：2007
• 卷：72
• 期：15
• 页码：5912 - 5915
• 全文大小：70K
• 年卷期：v.72,no.15(July 20, 2007)
• ISSN：1520-6904

文摘

A kinetic and product study of the reactions of chlorpromazine 1, N-methylphenothiazine 2, and N-ethylphenothiazine3 with singlet oxygen was carried out in MeOH and MeCN.1 undergoes exclusive side-chain cleavage, whereas thereactions of 2 and 3, in MeOH, afforded only the corresponding sulfoxides. A mechanism for the reaction of 1 isproposed where the first step involves an interaction betweensinglet oxygen and the side-chain dimethylamino nitrogen.This explains why no side-chain cleavage is observed for 2and 3.