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Vol. 27 No. 12 (2015): Vol 27 Issue 12

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Utility of Suzuki-Miyaura Cross-Coupling Reaction in Synthesis of Benzo[a]phenothiazine and Benzo[a]phenoxazine Derivatives and their Antimicrobial Screening

https://doi.org/10.14233/ajchem.2015.19182
Jude I. Ayogu
Department of Pure and Industrial Chemistry, Faculty of Physical Sciences, Synthetic Organic Chemistry Unit, University of Nigeria, Nsukka 410002, Nigeria
Benjamin E. Ezema
Department of Pure and Industrial Chemistry, Faculty of Physical Sciences, Synthetic Organic Chemistry Unit, University of Nigeria, Nsukka 410002, Nigeria
Chidimma G. Ezema
National Centre for Energy Research and Development, University of Nigeria, Nsukka, Nigeria

Corresponding Author(s) : Jude I. Ayogu

jude.ayogu@unn.edu.ng

Asian Journal of Chemistry, Vol. 27 No. 12 (2015): Vol 27 Issue 12

Abstract

Palladium-catalyzed Suzuki-Miyaura cross-coupling reactions of 6-chloro-5H-benzo[a]phenothiazin-5-one (1), 11-amino-6-chloro-9-thio-5H-naphtho[2,1-b]pyrimido[5,4-e][1,4]oxazin-5-one (2) and 6-chloro-5H-naphtho[2,1-b]pyrido[2,3-e][1,4]oxazin-5-one (3) with phenylboronic acid and 3-nitrophenylboronic acid were thoroughly investigated. The above intermediates were prepared by the reactions of 2-aminothiophenol, 4,5-diamino-6-hydroxylpyrimidine-2-thiol and 2-aminopyridin-3-ol each with 2,3-dichloronaphthalene-1,4-dione in a basic medium using benzene/DMF as the solvent. Thereafter, each was subjected to the Suzuki-Miyaura coupling reaction with phenylboronic acid and 3-nitrophenyl boronic acid, refluxing for 7-8 h at 110 °C using tris(dibenzylideneacetone)palladium(0), dicyclohexyl-phosphino-2',6'-dimethoxybiphenyl (SPhos), potassium phosphate and toluene as the catalyst, ligand, base and solvent correspondingly to yield the derivatives (1a-b), (2a-b) and (3a-b), respectively. Structures of the compounds were characterized using UV/visible spectrophotometry, FT-IR, 1H NMR and 13C NMR spectroscopy and elemental analysis. The compounds were screened against six micro-organisms, viz: Bacillus subtitis, Staphylococcus aureus, Pseudomonas aeruginosa, Escherichia coli, Candida albicans and Aspergillus niger and were shown to have significant activity against some Gram-positive micro-organisms.

Keywords

Suzuki-Miyaura cross-coupling reaction Benzo[a]phenothiazine Benzo[a]phenoxazine Antimicrobial screening
I. Ayogu, J., E. Ezema, B., & G. Ezema, C. (2015). Utility of Suzuki-Miyaura Cross-Coupling Reaction in Synthesis of Benzo[a]phenothiazine and Benzo[a]phenoxazine Derivatives and their Antimicrobial Screening. Asian Journal of Chemistry, 27(12), 4467–4473. https://doi.org/10.14233/ajchem.2015.19182
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