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.
The singlet oxygen oxidation of chlorpromazine and some phenothiazine derivatives. Products and reaction mechanisms / Baciocchi, Enrico; Tiziana Del, Giacco; Lanzalunga, Osvaldo; Lapi, Andrea; Raponi, Daniele. - In: JOURNAL OF ORGANIC CHEMISTRY. - ISSN 0022-3263. - 72:15(2007), pp. 5912-5915. [10.1021/jo0706980]
The singlet oxygen oxidation of chlorpromazine and some phenothiazine derivatives. Products and reaction mechanisms
BACIOCCHI, Enrico;LANZALUNGA, Osvaldo;LAPI, Andrea;RAPONI, DANIELE
2007
Abstract
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.I documenti in IRIS sono protetti da copyright e tutti i diritti sono riservati, salvo diversa indicazione.
