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

Hussein A. Emam; Saber M. Hassan; Ahmed M. El-Agrody; Ahmed H. Bedair; Mahmoud M. Abdelall

doi:doi:10.11648/j.ajhc.20160201.16

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

Hussein A. Emam, Saber M. Hassan, Ahmed M. El-Agrody, Ahmed H. Bedair, Mahmoud M. Abdelall

Published in American Journal of Heterocyclic Chemistry (Volume 2, Issue 1)

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.

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

Benzocoumarin, 1,3,4-Thiadiazol, Thiazolidinone

References

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APA Style

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://article.sciencepublishinggroup.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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Author Information

Hussein A. Emam

Chemistry Department, Faculty of Science, Al-Azhar University, Nasr City, Cairo, Egypt
Saber M. Hassan

Chemistry Department, Faculty of Science, Al-Azhar University, Nasr City, Cairo, Egypt
Ahmed M. El-Agrody

Chemistry Department, Faculty of Science, Al-Azhar University, Nasr City, Cairo, Egypt
Ahmed H. Bedair

Chemistry Department, Faculty of Science, Al-Azhar University, Nasr City, Cairo, Egypt
Mahmoud M. Abdelall

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

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APA Style

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

Copy | Download

@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://article.sciencepublishinggroup.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}
}

Copy | Download

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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