Synthesis of New N-Substituted Phenothiazine Derivatives

Suaad.M.Al.Araji,

	Synthesis of New N-Substituted Phenothiazine Derivatives
Al-Mustansiriyah Journal of Science
Article 1, Volume 21, Issue 5, 2010, Pages 134-147
Author

Abstract
The aim of the present work is synthesis of new phenothiazine derivatives containing N-substituted phenothiazine. To obtain these derivatives, the diphenyl amine was chosen as the starting material, which was heated for 6hrs with sulfur. In the presence of iodine at 270 C°, it gave the phenothiazine (1) Treatment of phenothiazine (1) with (chloroacetyl chloride) gave the N10 acetyl phenothiazine (2), which was treated with hydrazine hydrate to give the hydrazine (3). The hydrazine (3) was used for synthesis of two types of heterocyclic derivatives: - (a) N10 (4-phenyl – 1, 2, 4 - triazine – 3 – thiol) phenothiazine (5). (b) N10 (4-phenyl – 1,2,4- triazine – 3 – o1) phenothiazine (11). Compound (5) was synthesized by the intermolecular cyclization of thiosemicarbazide derivative (4), which was obtained from the reaction of the hydrazide (3) and phenyl isothiocynate. Compound (11) was synthesized in similar manner that used for the preparation of (5), by using semicarbazide derivative instead of thiosemicarbazide derivative. (c) Alkylation of N10 (4-phenyl–1,2,4-triazine–3–thio) phenothiazine (5) using different alkyl halides (chloro propane, bromo butane, chloro pentane, benzyl chloride) . (d) Alkylation of N10 (4- phenyl – 1, 2, 4-triazine-3-ol) phenothiazine (11) using different alkylhalides (chloro propane, bromo butane, chloro pentane, benzyl chloride) in basic condition.

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