Synthesis and Characterization of 6–(4-Bromophenyl)-10-methyl-11-azabenzo[a] phenothiazin-5-one

Ayuk, E.L. and ILO, S.U. and NJOKUNWOGBU, A.N and Engwa, G.A. and ONI, T.O. and Okoro, U.C (2015) Synthesis and Characterization of 6–(4-Bromophenyl)-10-methyl-11-azabenzo[a] phenothiazin-5-one. International Journal of Materials and Chemistry, 5 (2). pp. 44-47.

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Official URL: http://10.5923/j.ijmc.20150502.03


The synthesis of a new derivative of a non-linear azaphenothiazine of industrial importance, 6-(4-bromophenyl)-10-methyl-11-azabenzo[a]phenothiazin-5-one is reported. This was obtained via transition metal catalyzed cross coupling reaction. Alkaline hydrolysis of 2-amino-6-methyl thiozole [4,5b] pyridine in 20% sodium hydroxide solution and neutralization with acetic acid yielded 2-amino-6-methylpyridine-3-thiol. Base catalyzed (anhydrous Sodium carbonate) condensation of 2,3-dichoro-1,4-naphthoquinone and 2-amino-6-methylpyridine-3-thiol gave 6-chloro-10-methyl-11-azabezo[a]phenothiazin-5-one which coupled with 4-bromophenyl boronic acid in the presence of a transition metal catalyst system to furnish the new phenothiazine derivative above. The ease of oxidation of these new heterocyclic compounds to the corresponding sulphoxide using hydrogen peroxide, suggest their applicability as antioxidants in lubricant and fuel. The stability of the iminoquinoid system is attributed to ionic resonance effect.

Item Type: Article
Subjects: L Education > L Education (General)
Q Science > Q Science (General)
Divisions: Faculty of Natural and Applied Sciences
Depositing User: miss ifeoma agbo
Date Deposited: 18 Apr 2019 12:36
Last Modified: 18 Apr 2019 12:36

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