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DOI Prefix 10.20431 |
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International Journal of Advanced Research in Chemical Science
Volume-2 Issue-10, 2015, Page No:64-71
An Efficient Palladium Catalyzed Synthesis of Non-Linear 6, 8-Diaryl Diazaphenothiazinone Derivatives
Ayuk Eugene L1*, Nweke Cletus M1, Agu Ifeoma S2
1.Chemical Sciences Department, Faculty of Natural and Applied Sciences, Godfrey Okoye University, Ugwuomu-Nike, Enugu, Nigeria
2.Department of Chemical Engineering, Institute of Management and Technology, Enugu, Nigeria
2.Department of Chemical Engineering, Institute of Management and Technology, Enugu, Nigeria
Citation : Ayuk Eugene L,Nweke Cletus M,Agu Ifeoma S, An Efficient Palladium Catalyzed Synthesis of Non-Linear 6, 8-Diaryl Diazaphenothiazinone Derivatives International Journal of Advanced Research in Chemical Science. 2015;2(10):64-71.
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.
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