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Synthesis and Characterization of New Complex Heterocyclic Ring Systems of Industrial Importance

Received: 12 July 2016     Accepted: 19 December 2016     Published: 10 January 2017
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Abstract

The synthesis and characterization of new complex monoaza and pentaaza angular phenothiazine derivatives is reported. The first derivative, 6,10-dichloro-17-azadibenzo[a,n]triphenodithiazin-5,11-dione 10 was obtained by a base-catalyzed reaction of 2,6-diaminopyridine-3,5-dithiol 5 and 2,3-dichloro-1,4-naphthaquinone 9, while the second derivative, 7,9,15,17-tetraamino-6,8,16,18,25-pentazadibenzo[a,n]di([1,4]benzothaizino[3,2-c,l])triphenodiathizine 11 was obtained by the reaction of two moles of 2, 4, 6-triaminopyrimidine-3-thiol 8 and one mole of compound 10 under the same reaction conditions. The assigned structures to the above synthesized compounds were done on the basis of spectroscopic analysis.

Published in American Journal of Heterocyclic Chemistry (Volume 2, Issue 1)
DOI 10.11648/j.ajhc.20160201.15
Page(s) 26-31
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), 2017. Published by Science Publishing Group

Keywords

Monoaza, Pentaaza, Triphenodiathiazine, Triaminopyrimidine-3-Thiol, Phenothiazine

References
[1] Odin E. M; Onoja P. K. and Saleh J. F; Synthesis, characterization and neuropharmacological activity of angular pentacyclic phenothiazine. Int. J. Phy. Sc. 8 (26), 1374-1381, 2013.
[2] Sinha Shweta; Pandeja S. N; Verma Anopam; Yadav Deepika. Synthesis and biological activity of phenothiazine derivatives; Int. J Research in Ayurveda& Pharm. 2 (4), 1130-1137, 2011.
[3] Upendra Kumar; Kushwaha Yashovardhan; Sudhir Kumar Bhati and Asohok Kumar. Synthesis of new 10-substituted phenothiazines as Inflammatory and Analgesic Agents; Int. J. Pharm and Bio. Science, 1 (3), 1-10, 2010.
[4] Okafor C. O. Chemistry and applications of angular phenothiazines. Dyes and Pigments, 7 (4), 249-287, 1986.
[5] Massie S. P. The Chemistry of Phenothiazines. Chem. Rev, 54; 797-833, 1954.
[6] Massie S. P; Kadaba P. K; Ring Derivatives of Phenothiazines. The Synthesis of 1-substituted phenothiazines by Thionation; J. Org. Chem. 21: 347-348, 1956.
[7] Okafor C. O; Okerulu I. O; Okeke S. I; Vat dyes from new heterocyclic ring systems. Dyes and Pigments, 8, 11–24, 1987.
[8] 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, 3, 40-47, 2012.
[9] U. C. Okoro and B. E. Ezema; Synthesis of new non-linear diazaphenothiazine ring system. Int. Jour. Chem. 16, (2), 115-120, 2006.
[10] Okoro U. C; The first analogues of dibenzotriphenodithiazine ring systems. Ind. J. Chem. 30B (118), 22-24, 1991.
[11] B. E. Ezema; C. E. Ezema; D. I. Ugwu; Synthesis of a new and first triazadibenzo[a,n] triphenodithiazine. Chemical and Processing Engieering Research, 8, 35-41, 2013.
[12] U. C. Okoro and A. O. Ijeoma; Synthesis of new non-linear polycyclic diazaphenothiazine ring system. International Jour of Chem. 16, (4), 245-250, 2006.
[13] Okafor C. O; Anew type of angular phenothiazine ring system. Tetrahedron, 42 (10) 22771-80, 1986.
[14] Okoro U. C., Synthesis of a new branched benzoxazinoazaphenothiazine ring system. Ind. J. Chem. 30B, (18), 22-24, 1991.
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  • APA Style

    Ayuk Eugene Lakem, Nweke Cletus Mgadiugha, Ugwu Marigoretti Ogechukwu. (2017). Synthesis and Characterization of New Complex Heterocyclic Ring Systems of Industrial Importance. American Journal of Heterocyclic Chemistry, 2(1), 26-31. https://doi.org/10.11648/j.ajhc.20160201.15

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    ACS Style

    Ayuk Eugene Lakem; Nweke Cletus Mgadiugha; Ugwu Marigoretti Ogechukwu. Synthesis and Characterization of New Complex Heterocyclic Ring Systems of Industrial Importance. Am. J. Heterocycl. Chem. 2017, 2(1), 26-31. doi: 10.11648/j.ajhc.20160201.15

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    AMA Style

    Ayuk Eugene Lakem, Nweke Cletus Mgadiugha, Ugwu Marigoretti Ogechukwu. Synthesis and Characterization of New Complex Heterocyclic Ring Systems of Industrial Importance. Am J Heterocycl Chem. 2017;2(1):26-31. doi: 10.11648/j.ajhc.20160201.15

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  • @article{10.11648/j.ajhc.20160201.15,
      author = {Ayuk Eugene Lakem and Nweke Cletus Mgadiugha and Ugwu Marigoretti Ogechukwu},
      title = {Synthesis and Characterization of New Complex Heterocyclic Ring Systems of Industrial Importance},
      journal = {American Journal of Heterocyclic Chemistry},
      volume = {2},
      number = {1},
      pages = {26-31},
      doi = {10.11648/j.ajhc.20160201.15},
      url = {https://doi.org/10.11648/j.ajhc.20160201.15},
      eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.ajhc.20160201.15},
      abstract = {The synthesis and characterization of new complex monoaza and pentaaza angular phenothiazine derivatives is reported. The first derivative, 6,10-dichloro-17-azadibenzo[a,n]triphenodithiazin-5,11-dione 10 was obtained by a base-catalyzed reaction of 2,6-diaminopyridine-3,5-dithiol 5 and 2,3-dichloro-1,4-naphthaquinone 9, while the second derivative, 7,9,15,17-tetraamino-6,8,16,18,25-pentazadibenzo[a,n]di([1,4]benzothaizino[3,2-c,l])triphenodiathizine 11 was obtained by the reaction of two moles of 2, 4, 6-triaminopyrimidine-3-thiol 8 and one mole of compound 10 under the same reaction conditions. The assigned structures to the above synthesized compounds were done on the basis of spectroscopic analysis.},
     year = {2017}
    }
    

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    T1  - Synthesis and Characterization of New Complex Heterocyclic Ring Systems of Industrial Importance
    AU  - Ayuk Eugene Lakem
    AU  - Nweke Cletus Mgadiugha
    AU  - Ugwu Marigoretti Ogechukwu
    Y1  - 2017/01/10
    PY  - 2017
    N1  - https://doi.org/10.11648/j.ajhc.20160201.15
    DO  - 10.11648/j.ajhc.20160201.15
    T2  - American Journal of Heterocyclic Chemistry
    JF  - American Journal of Heterocyclic Chemistry
    JO  - American Journal of Heterocyclic Chemistry
    SP  - 26
    EP  - 31
    PB  - Science Publishing Group
    SN  - 2575-5722
    UR  - https://doi.org/10.11648/j.ajhc.20160201.15
    AB  - The synthesis and characterization of new complex monoaza and pentaaza angular phenothiazine derivatives is reported. The first derivative, 6,10-dichloro-17-azadibenzo[a,n]triphenodithiazin-5,11-dione 10 was obtained by a base-catalyzed reaction of 2,6-diaminopyridine-3,5-dithiol 5 and 2,3-dichloro-1,4-naphthaquinone 9, while the second derivative, 7,9,15,17-tetraamino-6,8,16,18,25-pentazadibenzo[a,n]di([1,4]benzothaizino[3,2-c,l])triphenodiathizine 11 was obtained by the reaction of two moles of 2, 4, 6-triaminopyrimidine-3-thiol 8 and one mole of compound 10 under the same reaction conditions. The assigned structures to the above synthesized compounds were done on the basis of spectroscopic analysis.
    VL  - 2
    IS  - 1
    ER  - 

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Author Information
  • Industrial Chemistry Unit, Chemical Sciences Department, Godfrey Okoye University, Ugwuomu-Nike, Enugu, Nigeria

  • Industrial Chemistry Unit, Chemical Sciences Department, Godfrey Okoye University, Ugwuomu-Nike, Enugu, Nigeria

  • Industrial Chemistry Unit, Chemical Sciences Department, Godfrey Okoye University, Ugwuomu-Nike, Enugu, Nigeria

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