An Efficient Palladium Catalyzed Synthesis of Non-Linear 6, 8-Diaryl Diazaphenothiazinone Derivatives

Ayuk, E.L. and Nweke, Cletus M. and Agu, Ifeoma S. (2015) An Efficient Palladium Catalyzed Synthesis of Non-Linear 6, 8-Diaryl Diazaphenothiazinone Derivatives. International Journal of Advanced Research in Chemical Science (IJARCS), 2 (10). pp. 64-71. ISSN 2349-0403

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Abstract

The synthesis of four new derivatives of 6,8-dichloro-10-amino-9,11-diazabenzo[a]phenothiazin-5-one, is reported in this article. One of the key intermediates 2,6-diamino-4-chloropyrimidin-3-thiol was obtained via the thiocyanation of 2,6-diamino-4-chloropyrimidine in the presence of bromine and acetic acid at -5oC to give 2,6-diamino-4-chloro-3-thiocynatopyrimidine. This was then subjected to hydrolysis in the presence of 20% sodium hydroxide to furnish the intermediate. The condensation of 2,3-dichloro-1,4-naphthoquinone with 2,6-diamino-4-chloropyrimidin-3-thiol gave 6,8-dichloro-10-amino-9,11-diazabenzo[a]phenothiazin-5-one. This azaphenothiazinone was coupled with four arylboronic acids in the presence of diphenyl phosphinobutane palladium chloride, Pd (dppb)2Cl (catalyst) and 1,4-bis-(2-hydroxy-3, 5-di-tert-butylbenzyl) piperazine (ligand) to furnish the four non-linear 6,8-diaryldiazaphenothiazine derivatives. The equations of reaction for the processes are shown below; Keywords: Catalyst, hydrolysis, thiocyanation, 6, 8-diaryldiazaphenothiazine6, 8-dichloro-10-amino-9, 11-diazabenzo[a]phenothiazin-5-one.

Item Type: Article
Subjects: L Education > L Education (General)
Q Science > Q Science (General)
Divisions: Faculty of Management and Social Sciences
Depositing User: miss ifeoma agbo
Date Deposited: 24 Apr 2019 13:44
Last Modified: 24 Apr 2019 13:44
URI: http://eprints.gouni.edu.ng/id/eprint/1239

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