The singlet oxygen oxidation of chlorpromazine and some phenothiazine derivatives. Products and reaction mechanisms |
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| Authors: | Baciocchi Enrico Del Giacco Tiziana Lanzalunga Osvaldo Lapi Andrea Raponi Daniele |
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| Institution: | Dipartimento di Chimica and Istituto CNR di Metodologie Chimiche-IMC, Sezione Meccanismi di Reazione c/o Dipartimento di Chimica, Sapienza Università di Roma, Piazzale A. Moro 5, 00185 Rome, Italy. enrico.baciocchi@uniroma1.it |
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| 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. |
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