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Vol. 27 No. 11 (2015): Vol 27 Issue 11

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Synthesis and Antimicrobial Screening of Novel Benzoxazinophenothiazine Derivatives

https://doi.org/10.14233/ajchem.2015.19110
C.O. Ike
Department of Pure and Industrial Chemistry, University of Nigeria, Nsukka, Nigeria
B.E. Ezema
Department of Pure and Industrial Chemistry, University of Nigeria, Nsukka, Nigeria
J.I. Ayogu
Department of Pure and Industrial Chemistry, University of Nigeria, Nsukka, Nigeria
D.I. Ugwu
Department of Pure and Industrial Chemistry, University of Nigeria, Nsukka, Nigeria
C.G. Ezema
National Centre for Energy Research and Development, University of Nigeria, Nsukka, Nigeria
A.P. Nwasi
Department of Pure and Industrial Chemistry, University of Nigeria, Nsukka, Nigeria
E.O. Adekola
Department of Pure and Industrial Chemistry, University of Nigeria, Nsukka, Nigeria

Corresponding Author(s) : J.I. Ayogu

jude.ayogu@unn.edu.ng

Asian Journal of Chemistry, Vol. 27 No. 11 (2015): Vol 27 Issue 11

Abstract

The acid catalyzed synthesis of benzoxazinophenothiazine derivatives is reported. The intermediates 6-chloro-5H-benzo[a]phenothiazin-5-one (1), 11-amino-6-chloro-9-thio-8,10-diazabenzo[a]phenoxazin-5-one (2) and 6,8-dichlorobenzo[a]phenoxazine-5-one (3) were prepared by the condensation of 2,3-dichloro-1,4-naphthoquinone with 2-aminothiophenol, 4,5-diamino-6-hydroxypyrimidin-2-thiol and 2-amino-6-chlorophenol respectively in an alkaline medium. Further alkaline condensation of the intermediates, 1 and 2 each with 4-aminothiophenol yielded 14-nitrobenzo[a][1,4]benzoxazino[3,2-c]phenothiazine and 15-amino-13-thio-12,14-diazabenzo[a][1,4]-benzoxazino[3,2-c]phenothiazine correspondingly. Another complex ring system, 12-chloro-9-methoxy-8-azabenzo[a][1,4]benzoxazino-[3,2-c]phenothiaizne was accomplished in a good yield by the condensation of 3 with 3-amino-6-methoxypyridin-2-thiol. The structural confirmation was done using UV-visible spectroscopy, FT-IR, 1H NMR, 13C NMR and elemental analysis. The synthesized compounds were screened against some micro-organisms and the results showed that the complex derivatives were significantly active against the microorganisms.

Keywords

Antimicrobial screening Acid catalysis Benzoxazinophenothiazine Diazabenzo derivatives Phenoxazin-5-ones
Ike, C., Ezema, B., Ayogu, J., Ugwu, D., Ezema, C., Nwasi, A., & Adekola, E. (2015). Synthesis and Antimicrobial Screening of Novel Benzoxazinophenothiazine Derivatives. Asian Journal of Chemistry, 27(11), 4115–4119. https://doi.org/10.14233/ajchem.2015.19110
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