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

Ayuk Eugene Lakem; Nweke Cletus M.; Agu Ifeoma S.

doi:doi:10.11648/j.sjc.20160401.12

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

Ayuk Eugene Lakem, Nweke Cletus M., Agu Ifeoma S.

Published in Science Journal of Chemistry (Volume 4, Issue 1)

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), 2024. Published by Science Publishing Group

Keywords

Synthesis, Hydrolysis, Condensation, Crystalline, Derivatives

References

[1]	Agata Jaszczyszyn; Kazimierz Gasiorowski; Piotr Switek; Wiesaw Malinka; Katarzyna Cieoelik-Boczula; Joanna Petrus; Bogusawa Czarnik-Matusewicz. Chemical structures of phenothiazines and their biological activity. Institute of Pharmarcology Polish Academy. 2012, 64, 16-23.
[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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APA Style

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
PY  - 2016
N1  - https://doi.org/10.11648/j.sjc.20160401.12
DO  - 10.11648/j.sjc.20160401.12
T2  - Science Journal of Chemistry
JF  - Science Journal of Chemistry
JO  - Science Journal of Chemistry
SP  - 9
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

Ayuk Eugene Lakem

Chemical Science Department, Faculty of Natural and Applied Sciences, Godfrey Okoye University, Ugwuomu-Nike, Enugu, Nigeria
Nweke Cletus M.

Chemical Science Department, Faculty of Natural and Applied Sciences, Godfrey Okoye University, Ugwuomu-Nike, Enugu, Nigeria
Agu Ifeoma S.

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

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APA Style

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
PY  - 2016
N1  - https://doi.org/10.11648/j.sjc.20160401.12
DO  - 10.11648/j.sjc.20160401.12
T2  - Science Journal of Chemistry
JF  - Science Journal of Chemistry
JO  - Science Journal of Chemistry
SP  - 9
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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