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Synthesis of Novel Pyrimido Thiazine and Their Derivatives

Received: 18 May 2019     Accepted: 19 June 2019     Published: 29 June 2019
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Abstract

In present report novel thiazines were prepared from starting materials chalcone and thiourea. The resulting compound 6-(4-methoxyphenyl) 4-phenyl-6H-1, 3-thiazin-2-amine (2) was further reacted with ethyl 2-cyano-3, 3-bis (methylthio) acrylate in the presence of catalytic amount of potassium carbonate in DMF under reflux condition that offered novel 2-(4-methoxyphenyl) 8-(methylthio)-6-0xo-4-phenyl-4, 6, 9, 9a-tetrahydropyrimido [2, 1-b] [1, 3]-thiazine-7-carbonitrile (3). The synthesized compounds were characterized by spectral methods. The compound (3) possesses replaceable methylthio (-SCH3) group at 8 position. The compound (3) react with various nucleophiles like substituted aromatic amines, aromatic phenols, hetryl amines and active methylene compounds to give 2-(4-methoxyphenyl)-8-substituted-6-oxo-4-phenyl-4, 6, 9, 9a-tetrahydropyrimido [2, 1-b] [1, 3] thiazine-7-carbonitrile in good yields.

Published in American Journal of Heterocyclic Chemistry (Volume 5, Issue 2)
DOI 10.11648/j.ajhc.20190502.11
Page(s) 23-26
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), 2019. Published by Science Publishing Group

Keywords

Claisen-Schmidt Condensation, 2-Cyano-3, 3-Bis (Methylthio) Acrylate,Michael Addition Reaction, Thiazines

References
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[4] Mamoru Kokestu, Kohsuke Tanaka, Yuichi Takenaka, Cecil D, Kwong and Hideharu Ishihara, Synthesis of 1, 3-thiazine derivatives and their evaluation as potential antimycobacterial agents, European j pharm. Sci., April 2002, volume 15, Issue 3, Pg. no. 307-310.
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[7] Li Fu, Li Fu, Ding Ye, Ying Li and Shufan Yin, Synthesis and claiming activity of 6H-2-Amino-4-Aryl-6-(4-b-D-Allopyranosyloxyphenyl)-1, 3-thiazine, Chemistry of natural products, vol.46, no.2, 169-172.
[8] Zawisza, Synthesis and pharmacological analysis of new derivatives of tetrahydro-[1, 3]-thiazine and 2-thiobarbituric acid, National center for biotechnology information, 1981; 29 (2), 235-48.
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[13] Campaigne E and Nargund P K 1964 J. Org. Chem. 29 224.
[14] Dana W. Mayo, Ronald M. Pike, David C. Forbes; Microscale Organic Labor-atory; with Multistep and Multiscale Synthesis, (2010) 308-310.
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[16] Jain AC, Prasad AK (1995) Reaction of chalcone 2-4,-dimethoxychalcone, a-bromo and methoxy chalcone with thiourea. Indian J Chem 34B: 496. 14.
[17] Sambhaji PV, Vijay NB, Sandeep V. Khansole, Ramdas NK (2009) A convenient one pot synthesis of 3-cyano-9-methyl-2-methylthio-4-0xo-4H-pyrimidi-[2, 1-b] [4, 5-b] quinolone and its reaction with selected nucleophiles. Letters in organic chemistry 6: 544-548.
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    Sirsat Shivraj Balajirao, Jadhav Anilkumar Govindrao, Kale Prashant Sambharao, Jadhav Madhav Sopanrao. (2019). Synthesis of Novel Pyrimido Thiazine and Their Derivatives. American Journal of Heterocyclic Chemistry, 5(2), 23-26. https://doi.org/10.11648/j.ajhc.20190502.11

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    ACS Style

    Sirsat Shivraj Balajirao; Jadhav Anilkumar Govindrao; Kale Prashant Sambharao; Jadhav Madhav Sopanrao. Synthesis of Novel Pyrimido Thiazine and Their Derivatives. Am. J. Heterocycl. Chem. 2019, 5(2), 23-26. doi: 10.11648/j.ajhc.20190502.11

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    AMA Style

    Sirsat Shivraj Balajirao, Jadhav Anilkumar Govindrao, Kale Prashant Sambharao, Jadhav Madhav Sopanrao. Synthesis of Novel Pyrimido Thiazine and Their Derivatives. Am J Heterocycl Chem. 2019;5(2):23-26. doi: 10.11648/j.ajhc.20190502.11

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  • @article{10.11648/j.ajhc.20190502.11,
      author = {Sirsat Shivraj Balajirao and Jadhav Anilkumar Govindrao and Kale Prashant Sambharao and Jadhav Madhav Sopanrao},
      title = {Synthesis of Novel Pyrimido Thiazine and Their Derivatives},
      journal = {American Journal of Heterocyclic Chemistry},
      volume = {5},
      number = {2},
      pages = {23-26},
      doi = {10.11648/j.ajhc.20190502.11},
      url = {https://doi.org/10.11648/j.ajhc.20190502.11},
      eprint = {https://article.sciencepublishinggroup.com/pdf/10.11648.j.ajhc.20190502.11},
      abstract = {In present report novel thiazines were prepared from starting materials chalcone and thiourea. The resulting compound 6-(4-methoxyphenyl) 4-phenyl-6H-1, 3-thiazin-2-amine (2) was further reacted with ethyl 2-cyano-3, 3-bis (methylthio) acrylate in the presence of catalytic amount of potassium carbonate in DMF under reflux condition that offered novel 2-(4-methoxyphenyl) 8-(methylthio)-6-0xo-4-phenyl-4, 6, 9, 9a-tetrahydropyrimido [2, 1-b] [1, 3]-thiazine-7-carbonitrile (3). The synthesized compounds were characterized by spectral methods. The compound (3) possesses replaceable methylthio (-SCH3) group at 8 position. The compound (3) react with various nucleophiles like substituted aromatic amines, aromatic phenols, hetryl amines and active methylene compounds to give 2-(4-methoxyphenyl)-8-substituted-6-oxo-4-phenyl-4, 6, 9, 9a-tetrahydropyrimido [2, 1-b] [1, 3] thiazine-7-carbonitrile in good yields.},
     year = {2019}
    }
    

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  • TY  - JOUR
    T1  - Synthesis of Novel Pyrimido Thiazine and Their Derivatives
    AU  - Sirsat Shivraj Balajirao
    AU  - Jadhav Anilkumar Govindrao
    AU  - Kale Prashant Sambharao
    AU  - Jadhav Madhav Sopanrao
    Y1  - 2019/06/29
    PY  - 2019
    N1  - https://doi.org/10.11648/j.ajhc.20190502.11
    DO  - 10.11648/j.ajhc.20190502.11
    T2  - American Journal of Heterocyclic Chemistry
    JF  - American Journal of Heterocyclic Chemistry
    JO  - American Journal of Heterocyclic Chemistry
    SP  - 23
    EP  - 26
    PB  - Science Publishing Group
    SN  - 2575-5722
    UR  - https://doi.org/10.11648/j.ajhc.20190502.11
    AB  - In present report novel thiazines were prepared from starting materials chalcone and thiourea. The resulting compound 6-(4-methoxyphenyl) 4-phenyl-6H-1, 3-thiazin-2-amine (2) was further reacted with ethyl 2-cyano-3, 3-bis (methylthio) acrylate in the presence of catalytic amount of potassium carbonate in DMF under reflux condition that offered novel 2-(4-methoxyphenyl) 8-(methylthio)-6-0xo-4-phenyl-4, 6, 9, 9a-tetrahydropyrimido [2, 1-b] [1, 3]-thiazine-7-carbonitrile (3). The synthesized compounds were characterized by spectral methods. The compound (3) possesses replaceable methylthio (-SCH3) group at 8 position. The compound (3) react with various nucleophiles like substituted aromatic amines, aromatic phenols, hetryl amines and active methylene compounds to give 2-(4-methoxyphenyl)-8-substituted-6-oxo-4-phenyl-4, 6, 9, 9a-tetrahydropyrimido [2, 1-b] [1, 3] thiazine-7-carbonitrile in good yields.
    VL  - 5
    IS  - 2
    ER  - 

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Author Information
  • Post Graduate Research Centre, Department of Chemistry, Yeshwant Mahavidyalaya, Nanded, India

  • Post Graduate Research Centre, Department of Chemistry, Yeshwant Mahavidyalaya, Nanded, India

  • Post Graduate Research Centre, Department of Chemistry, Yeshwant Mahavidyalaya, Nanded, India

  • Post Graduate Research Centre, Department of Chemistry, Yeshwant Mahavidyalaya, Nanded, India

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