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Synthesis and Characterization of Non-linear 6, 8 and 9, 12-Dichloroazaphenothiazine Derivatives

Received: 25 November 2015     Accepted: 10 December 2015     Published: 2 March 2016
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Abstract

The synthesis of non-linear diaza and tetraaza dichlorophenothiazine derivatives is reported in this article. This was achieved through the thiocyanation of 2,6-diamino-4-chloropyrimidine using potassium thiocyanate, bromine and glacial acetic acid at –5°C to give 2,6-diamino-3-thiocynatopyrimidine, which was hydrolyzed using 20% sodium hydroxide to furnish 2, 6-diamino-4-chloropyrimidin-3-thiol. Base catalyzed condensation reaction of 2, 6-diamino-4-chloropyrimidin-3-thiol and 2, 3-dichloro-1, 4-naphthoquinone gave the first derivative, 10-amino-6, 8-dichloro-9, 11-diazabenzo [a] phenthiazin-5-one, a reddish crystalline product. Similarly, another condensation reaction of 2, 6-diamino-4-chloropyrimidin-3-thiol with the first derivative, 10-amino-6, 8-dichloro-9, 11-diazabenzo[a]phenthiazin-5-one using the same reaction conditions, furnished the second derivative known as 7, 14-diamino-9,12-dichloro-6, 8, 13, 15-tetraazabenzo [a] [1,4] benzothiazino-[3,2-c] phenothiazine, a deep reddish crystalline compound. The synthesized compounds were characterized on the basis of UV-Visible, IR, 1HNMR and 13CNMR spectra data.

Published in Science Journal of Chemistry (Volume 4, Issue 1)
DOI 10.11648/j.sjc.20160401.12
Page(s) 9-13
Creative Commons

This is an Open Access article, distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution and reproduction in any medium or format, provided the original work is properly cited.

Copyright

Copyright © The Author(s), 2016. Published by Science Publishing Group

Keywords

Synthesis, Hydrolysis, Condensation, Crystalline, Derivatives

References
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[2] Raval J; Desai KK. Synthesis and antimicrobial activity of new triazolopyridinyl Phenothiazines. ARKIVOC 2005; xiii: 21.
[3] Smith N. L; Formation and oxidation of some phenothiazine derivatives. J. Org. Chem. 1951: 16: 415-418.
[4] Massie S. P. The Chemistry of Phenothiazines, Chem. Rev 1954; 54; 797-833.
[5] Massie S. P; Kadaba P. K; Ring Derivatives of Phenothiazines. The Synthesis of 1-substituted Phenothiazines by Thionation. J. Org. Chem. 1956: 21: 347-348.
[6] Okafor, C. O. Chemistry and applications of angular phenothiazines. Dyes and Pigments, 1986, 7 (4), 249-287.
[7] Okafor, C. O; Okerulu I. O; Okeke S. I; Vat dyes from new heterocyclic ring systems. Dyes and Pigments 1987, 8, 11–24.
[8] Gupta R. R., Kumar M; Synthesis, properties and reactions of phenothiazines in Phenothiazines and 1,4-Benzothiazines; Chemical and Biomedical Aspects, 1988, Gupta R. R. Ed, pp 1-46 Elsevier, Amsterdam.
[9] Okoro, U. C; The first analogues of dibenzotriphenodithiazine ring systems. Ind. J. Chem. 1991, 30B (118), 22-24.
[10] Odin E. M; Onoja P. K. and Saleh J. F; Synthesis, characterization and neuropharmacological activity of angular pentacyclic phenothiazine. Int. J. Phy. Sc. 2013, 8 (26), 1374-1381.
[11] Amit R. Trivedi; Arif B. Siddiqui; and Viresh H. Shah. Design, synthesis, characterization and antitubercular activity of some 2-heterocycle-substituted phenothiazines. ARKIVOC 2008 (ii) 210-217.
[12] B. E. Ezema; C. O. Okafor; C. G. Ezema and A. E. Onoabedje. Synthesis of new diaza angular and tetraazacomplex phenothiazine rings. Chemical and Processing Engineering Research, 2012 3, 40-47.
[13] Ayuk, E. L; A. N Njokunwogbu; S. U. Ilo; G. A. Engwa; T. O. Oni; I. k. Obiudu. Synthesis of New Tetracyclic and Hexacyclic Non-Linear Phenothiazine Derivatives. Int. Journal of Scientific & Engineering Research, 2015, 6, 1-8.
[14] Ayuk, Eugene L; Nweke, Cletus M; Agu, Ifeoma S; An Efficient Palladium Catalyzed Synthesis of Non-Linear 6, 8, Diaryl Diazaphenothiazinone Derivatives. Int.Journal of Advanced Research in Chemical Science, 2015, 2, 64-71.
[15] Okoro, U. C. and Ofoefule, A. U.; Synthesis of aza angular Phenothiazines (2008), Ind. Journal Chem. 18(13) 109-115.
[16] Okoro U. C and Ezema B. E. Synthesis of 1, 11-diaza-5H-benzo [a] phenothiazine-5-one. (2006), IJC 16(2), 115-120.
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    Ayuk Eugene Lakem, Nweke Cletus M., Agu Ifeoma S. (2016). Synthesis and Characterization of Non-linear 6, 8 and 9, 12-Dichloroazaphenothiazine Derivatives. Science Journal of Chemistry, 4(1), 9-13. https://doi.org/10.11648/j.sjc.20160401.12

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    ACS Style

    Ayuk Eugene Lakem; Nweke Cletus M.; Agu Ifeoma S. Synthesis and Characterization of Non-linear 6, 8 and 9, 12-Dichloroazaphenothiazine Derivatives. Sci. J. Chem. 2016, 4(1), 9-13. doi: 10.11648/j.sjc.20160401.12

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    AMA Style

    Ayuk Eugene Lakem, Nweke Cletus M., Agu Ifeoma S. Synthesis and Characterization of Non-linear 6, 8 and 9, 12-Dichloroazaphenothiazine Derivatives. Sci J Chem. 2016;4(1):9-13. doi: 10.11648/j.sjc.20160401.12

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  • @article{10.11648/j.sjc.20160401.12,
      author = {Ayuk Eugene Lakem and Nweke Cletus M. and Agu Ifeoma S.},
      title = {Synthesis and Characterization of Non-linear 6, 8 and 9, 12-Dichloroazaphenothiazine Derivatives},
      journal = {Science Journal of Chemistry},
      volume = {4},
      number = {1},
      pages = {9-13},
      doi = {10.11648/j.sjc.20160401.12},
      url = {https://doi.org/10.11648/j.sjc.20160401.12},
      eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.sjc.20160401.12},
      abstract = {The synthesis of non-linear diaza and tetraaza dichlorophenothiazine derivatives is reported in this article. This was achieved through the thiocyanation of 2,6-diamino-4-chloropyrimidine using potassium thiocyanate, bromine and glacial acetic acid at –5°C to give 2,6-diamino-3-thiocynatopyrimidine, which was hydrolyzed using 20% sodium hydroxide to furnish 2, 6-diamino-4-chloropyrimidin-3-thiol. Base catalyzed condensation reaction of 2, 6-diamino-4-chloropyrimidin-3-thiol and 2, 3-dichloro-1, 4-naphthoquinone gave the first derivative, 10-amino-6, 8-dichloro-9, 11-diazabenzo [a] phenthiazin-5-one, a reddish crystalline product. Similarly, another condensation reaction of 2, 6-diamino-4-chloropyrimidin-3-thiol with the first derivative, 10-amino-6, 8-dichloro-9, 11-diazabenzo[a]phenthiazin-5-one using the same reaction conditions, furnished the second derivative known as 7, 14-diamino-9,12-dichloro-6, 8, 13, 15-tetraazabenzo [a] [1,4] benzothiazino-[3,2-c] phenothiazine, a deep reddish crystalline compound. The synthesized compounds were characterized on the basis of UV-Visible, IR, 1HNMR and 13CNMR spectra data.},
     year = {2016}
    }
    

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  • TY  - JOUR
    T1  - Synthesis and Characterization of Non-linear 6, 8 and 9, 12-Dichloroazaphenothiazine Derivatives
    AU  - Ayuk Eugene Lakem
    AU  - Nweke Cletus M.
    AU  - Agu Ifeoma S.
    Y1  - 2016/03/02
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    DO  - 10.11648/j.sjc.20160401.12
    T2  - Science Journal of Chemistry
    JF  - Science Journal of Chemistry
    JO  - Science Journal of Chemistry
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    EP  - 13
    PB  - Science Publishing Group
    SN  - 2330-099X
    UR  - https://doi.org/10.11648/j.sjc.20160401.12
    AB  - The synthesis of non-linear diaza and tetraaza dichlorophenothiazine derivatives is reported in this article. This was achieved through the thiocyanation of 2,6-diamino-4-chloropyrimidine using potassium thiocyanate, bromine and glacial acetic acid at –5°C to give 2,6-diamino-3-thiocynatopyrimidine, which was hydrolyzed using 20% sodium hydroxide to furnish 2, 6-diamino-4-chloropyrimidin-3-thiol. Base catalyzed condensation reaction of 2, 6-diamino-4-chloropyrimidin-3-thiol and 2, 3-dichloro-1, 4-naphthoquinone gave the first derivative, 10-amino-6, 8-dichloro-9, 11-diazabenzo [a] phenthiazin-5-one, a reddish crystalline product. Similarly, another condensation reaction of 2, 6-diamino-4-chloropyrimidin-3-thiol with the first derivative, 10-amino-6, 8-dichloro-9, 11-diazabenzo[a]phenthiazin-5-one using the same reaction conditions, furnished the second derivative known as 7, 14-diamino-9,12-dichloro-6, 8, 13, 15-tetraazabenzo [a] [1,4] benzothiazino-[3,2-c] phenothiazine, a deep reddish crystalline compound. The synthesized compounds were characterized on the basis of UV-Visible, IR, 1HNMR and 13CNMR spectra data.
    VL  - 4
    IS  - 1
    ER  - 

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Author Information
  • Chemical Science Department, Faculty of Natural and Applied Sciences, Godfrey Okoye University, Ugwuomu-Nike, Enugu, Nigeria

  • Chemical Science Department, Faculty of Natural and Applied Sciences, Godfrey Okoye University, Ugwuomu-Nike, Enugu, Nigeria

  • Department of Chemical Engineering, Institute of Management and Technology, Enugu, Nigeria

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