American Journal of Heterocyclic Chemistry

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Synthesis of Some New N-[1-(Benzocoumarin-3`-yl)Ethylidene]Hydrazonothiazolidine, Thiazole and 1, 3, 4-Thidiazole Derivatives

Received: 10 December 2016    Accepted: 22 December 2016    Published: 12 January 2017
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Abstract

Condensation of 3-acetylbenzo[5,6]coumarin (1) with hydrazine-carbodithioate esters and/or thiocarbohydrazide gave the corresponding N-[1-(benzocoumarin-3`-yl)ethylidene]hydrazonecarbodithioate (2a,b) and 1,5-bis[1-(benzocoumarin-3`-yl)ethylidene]thiocarbohydrazide (3) respectively. Treatment of 2a with ethanolic ammonia solution and/or amines gave the corresponding thiosemicarbazone derivatives (4a-f). The reactions of 4a-f with ethyl bromoacetate/AcONa and ω-bromo derivatives were investigated, where thiazolidinones 5, 6 and thiazoles (9a,b) were obtained. Moreover, hydrazonecarbodithioate (2) underwent heterocycliczation upon treatment with hydrazonoyl halides (10) with Et3N to give the corresponding 2,3-dihydro-1,3,4-thiadiazoles (11a-d) via 1,3-dipolar cycloaddition and/or nuclophilic substiution. The structures of the new derivatives were elucidated by elemental analysis, IR, PMR and mass spectra.

DOI 10.11648/j.ajhc.20160201.16
Published in American Journal of Heterocyclic Chemistry (Volume 2, Issue 1, December 2016)
Page(s) 32-38
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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

Benzocoumarin, 1,3,4-Thiadiazol, Thiazolidinone

References
[1] S. Wawzonek, Heterocyclic Compounds,2, 173, (1975).
[2] F. M. Dean, Naturally occurring oxygen ring compounds, (Butter Worths, London) 176, 1963.
[3] R. Livingstone, Rod's Chemistry of carbon compounds, Vol. 4, 2nd Edn (Elsevier, Amsterdam) 1996.
[4] A. R. Kartritzky, C. W. Rees; Comprehensive heterocyclic chemistry vol. 3 (Bergaman Press, Oxford) (1984).
[5] J. Starnoton, comprehensive organic chemistry Vol. 4, edited by DHR Barton, W D Ollis (Pergaman Press, Oxford 629, (1979).
[6] M. D. Freiendmann, P. L. Stoller, T. H. Porter, and K. J. Folkevs; J. Med. Chem., 16, 1314 (1973).
[7] A. S. Hamam, and H. S. El-Kasher, Egyptian Pharmaceutical Congress Cairo, 7-10 Dec. (1975).
[8] R. D. Westl, M. H. Lin, Cooly (Jr) R. A. Zuviester M. L., and M. M. Grenan, J. Med. Chem., 16, 328 (1973).
[9] P. S. Furmer, C. C. Heung, and M. K. Luie, J. Med. Chem., 16, 411 (1973).
[10] M. S. Y. Khan and P. Sharma, Indian. J. Chem., 32B, 374 (1993).
[11] D. I. Brahmbhatt, G. B. Radji, S. U. Pandya, and U. R. Pandya; Indian J. Chem., 38B, 212 (1999).
[12] M. S. Y. Khan and P. Sharma, Indian J. Chem., 34B, 237 (1995).
[13] H. Sun, W. Hua and L. Chen, Bull. Soc. Chem. Belg., 106, 47 (1997).
[14] H. Sun, W. Hua and L. Chen,Chem. J. Chin. Univ., 18, 730 (1997).
[15] G. S. S. Murthi, M. Basak, J. Indian Chem. Soc. 70 (2), 170 (1993).
[16] D. L. Klayman, J. F. Bartosevichm, T. S. Griffin, C. J. Mason and J. P. Scovill; J. Med. Chem., 22, 855 (1979).
[17] J. Korosi, Ger. Offen. 1, 934, 89929 Jan (1979), C. A. 72, 100334s (1970).
[18] U. Verabhadra and V. Rajeswar, J. Indian Chem. Soc., 67 (1), 81 (1990).
[19] V. Yakazakov and I. Ya Potovski, Inv. Yashikucheb. Zavedii Khim. Ikhim. Technol. 4, 238 (1961) C. A., 55, 23415 (1961).
[20] P. Czerny and H. Hartmann, J. Prakt. Chem., 325, 551 (1983).
[21] N. F. Weiss and A. O. Abdelhamide, J. Heterocycl. Chem.,17, 1713 (1980).
[22] M. Nagakura, T. Ota, N. Shimadzu, K. Kawamura, Y. Eto; and Y. Wada, J. of Med. Chem., 22, 48 (1979).
[23] A. S. Shawali and A. O. Abdelhamide, Bull. Soc. Japan, 49, 321 (1976).
Author Information
  • Chemistry Department, Faculty of Science, Al-Azhar University, Nasr City, Cairo, Egypt

  • Chemistry Department, Faculty of Science, Al-Azhar University, Nasr City, Cairo, Egypt

  • Chemistry Department, Faculty of Science, Al-Azhar University, Nasr City, Cairo, Egypt

  • Chemistry Department, Faculty of Science, Al-Azhar University, Nasr City, Cairo, Egypt

  • Chemistry Department, Faculty of Science and Arts, Al-Baha University, Al-Baha, Saudi Arabia

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    Hussein A. Emam, Saber M. Hassan, Ahmed M. El-Agrody, Ahmed H. Bedair, Mahmoud M. Abdelall. (2017). Synthesis of Some New N-[1-(Benzocoumarin-3`-yl)Ethylidene]Hydrazonothiazolidine, Thiazole and 1, 3, 4-Thidiazole Derivatives. American Journal of Heterocyclic Chemistry, 2(1), 32-38. https://doi.org/10.11648/j.ajhc.20160201.16

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    ACS Style

    Hussein A. Emam; Saber M. Hassan; Ahmed M. El-Agrody; Ahmed H. Bedair; Mahmoud M. Abdelall. Synthesis of Some New N-[1-(Benzocoumarin-3`-yl)Ethylidene]Hydrazonothiazolidine, Thiazole and 1, 3, 4-Thidiazole Derivatives. Am. J. Heterocycl. Chem. 2017, 2(1), 32-38. doi: 10.11648/j.ajhc.20160201.16

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    AMA Style

    Hussein A. Emam, Saber M. Hassan, Ahmed M. El-Agrody, Ahmed H. Bedair, Mahmoud M. Abdelall. Synthesis of Some New N-[1-(Benzocoumarin-3`-yl)Ethylidene]Hydrazonothiazolidine, Thiazole and 1, 3, 4-Thidiazole Derivatives. Am J Heterocycl Chem. 2017;2(1):32-38. doi: 10.11648/j.ajhc.20160201.16

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  • @article{10.11648/j.ajhc.20160201.16,
      author = {Hussein A. Emam and Saber M. Hassan and Ahmed M. El-Agrody and Ahmed H. Bedair and Mahmoud M. Abdelall},
      title = {Synthesis of Some New N-[1-(Benzocoumarin-3`-yl)Ethylidene]Hydrazonothiazolidine, Thiazole and 1, 3, 4-Thidiazole Derivatives},
      journal = {American Journal of Heterocyclic Chemistry},
      volume = {2},
      number = {1},
      pages = {32-38},
      doi = {10.11648/j.ajhc.20160201.16},
      url = {https://doi.org/10.11648/j.ajhc.20160201.16},
      eprint = {https://download.sciencepg.com/pdf/10.11648.j.ajhc.20160201.16},
      abstract = {Condensation of 3-acetylbenzo[5,6]coumarin (1) with hydrazine-carbodithioate esters and/or thiocarbohydrazide gave the corresponding N-[1-(benzocoumarin-3`-yl)ethylidene]hydrazonecarbodithioate (2a,b) and 1,5-bis[1-(benzocoumarin-3`-yl)ethylidene]thiocarbohydrazide (3) respectively. Treatment of 2a with ethanolic ammonia solution and/or amines gave the corresponding thiosemicarbazone derivatives (4a-f). The reactions of 4a-f with ethyl bromoacetate/AcONa and ω-bromo derivatives were investigated, where thiazolidinones 5, 6 and thiazoles (9a,b) were obtained. Moreover, hydrazonecarbodithioate (2) underwent heterocycliczation upon treatment with hydrazonoyl halides (10) with Et3N to give the corresponding 2,3-dihydro-1,3,4-thiadiazoles (11a-d) via 1,3-dipolar cycloaddition and/or nuclophilic substiution. The structures of the new derivatives were elucidated by elemental analysis, IR, PMR and mass spectra.},
     year = {2017}
    }
    

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  • TY  - JOUR
    T1  - Synthesis of Some New N-[1-(Benzocoumarin-3`-yl)Ethylidene]Hydrazonothiazolidine, Thiazole and 1, 3, 4-Thidiazole Derivatives
    AU  - Hussein A. Emam
    AU  - Saber M. Hassan
    AU  - Ahmed M. El-Agrody
    AU  - Ahmed H. Bedair
    AU  - Mahmoud M. Abdelall
    Y1  - 2017/01/12
    PY  - 2017
    N1  - https://doi.org/10.11648/j.ajhc.20160201.16
    DO  - 10.11648/j.ajhc.20160201.16
    T2  - American Journal of Heterocyclic Chemistry
    JF  - American Journal of Heterocyclic Chemistry
    JO  - American Journal of Heterocyclic Chemistry
    SP  - 32
    EP  - 38
    PB  - Science Publishing Group
    SN  - 2575-5722
    UR  - https://doi.org/10.11648/j.ajhc.20160201.16
    AB  - Condensation of 3-acetylbenzo[5,6]coumarin (1) with hydrazine-carbodithioate esters and/or thiocarbohydrazide gave the corresponding N-[1-(benzocoumarin-3`-yl)ethylidene]hydrazonecarbodithioate (2a,b) and 1,5-bis[1-(benzocoumarin-3`-yl)ethylidene]thiocarbohydrazide (3) respectively. Treatment of 2a with ethanolic ammonia solution and/or amines gave the corresponding thiosemicarbazone derivatives (4a-f). The reactions of 4a-f with ethyl bromoacetate/AcONa and ω-bromo derivatives were investigated, where thiazolidinones 5, 6 and thiazoles (9a,b) were obtained. Moreover, hydrazonecarbodithioate (2) underwent heterocycliczation upon treatment with hydrazonoyl halides (10) with Et3N to give the corresponding 2,3-dihydro-1,3,4-thiadiazoles (11a-d) via 1,3-dipolar cycloaddition and/or nuclophilic substiution. The structures of the new derivatives were elucidated by elemental analysis, IR, PMR and mass spectra.
    VL  - 2
    IS  - 1
    ER  - 

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