European Journal of Chemistry 2014, 5(2), 296-304 | doi: https://doi.org/10.5155/eurjchem.5.2.296-304.1001 | Get rights and content






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Utility of thiocarbamoyl moiety in synthesis of some new sulphur containing heterocyclic compounds and evaluation of their antimicrobial activity


Ahmed Fadda (1,*) , Hala Refat (2) , Shimaa Kamal (3)

(1) Department of Chemistry, Faculty of Science, Mansoura University, 35516 Mansoura, Egypt.
(2) Department of Chemistry, Faculty of Education, Suez Canal University, 35516 Al-Arish, Egypt
(3) Department of Chemistry, Faculty of Science, Mansoura University, 35516 Mansoura, Egypt.
(*) Corresponding Author

Received: 09 Dec 2013 | Revised: 08 Jan 2014 | Accepted: 28 Jan 2014 | Published: 30 Jun 2014 | Issue Date: June 2014

Abstract


The reaction of N,N'-(1,4-phenylene)bis(2-cyanoacetamide) (1) with phenyl isothiocyanate gave thiocarbamoyl derivative 3, which reacted with α-halocarbonyl compounds in a mixture of ethanol:N,N-dimethylformamide in the presence of triethylamineto afford thiazoles 4, 7, 10 and thiophene12 derivatives. While, when the same reaction was refluxed in a mixture of ethanol:N,N-dimethylformamide only afforded the acyclic compounds 5, 6, 8, 9 and 11, which when refluxed in N,N-dimethylformamide in presence of triethylamine gave the corresponding above thiazole and thiophene derivatives. Moreover, the reaction of compound 3 with dihalo compounds afforded cyclic dithio derivatives 13a, 13b and 14. The newly synthesized compounds were characterized by analytical, spectral data and evaluation of their antimicrobial activities of 4, 7, 14 and 15 have a high antimicrobial activity.


Keywords


Thiazoles; Thiophene; Thiocarbamoyl; Antimicrobial activity; Cyclic dithio compounds; N,N'-(1,4-Phenylene)bis(2-cyanoacetamide)

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DOI: 10.5155/eurjchem.5.2.296-304.1001

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Funding information


Chemistry Department, Faculty of Science, Mansoura University, Egypt

Citations

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[1]. Ali M. S. Hebishy, Galal H. Elgemeie, Ahmed H. M. Elwahy
Novel Bis(2‐cyanoketene‐ S , S ‐/ S , N ‐acetals): Versatile Precursors for Novel Bis(aminopyrazole) Derivatives
Journal of Heterocyclic Chemistry  56(5), 1581, 2019
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[2]. Elsherbiny H. El-Sayed, Ahmed A. Fadda
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Journal of Heterocyclic Chemistry  55(10), 2251, 2018
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[3]. Jianxing Zhuang, Shutao Ma
Recent Development of Pyrimidine‐Containing Antimicrobial Agents
ChemMedChem  15(20), 1875, 2020
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[4]. Hala M. Refat, Ahmed A. Fadda, Rasha E. El-Mekawy, Aliaa M. Sleat
Synthesis of Some Novel Thieno[3,2-d]pyrimidine Derivatives of Pharmaceutical Interest
HETEROCYCLES  91(12), 2271, 2015
DOI: 10.3987/COM-15-13321
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[5]. Sobhi M. Gomha, Magda A. Abdallah, Mohamad R. Abdelaziz, Nany S. Eldin Serag
Synthesis of Some Novel Thiadiazoles and Thiazoles Linked to Pyrazole Ring
HETEROCYCLES  92(4), 649, 2016
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[6]. Hala M. Refat, A. A. Fadda, Shimaa Kamal
Synthesis and antitumor evaluation of some new biscarboxamidocoumarin and chromene derivatives
Journal of the Iranian Chemical Society  12(5), 845, 2015
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[7]. Ahmed A. Fadda, Eman H. Tawfik, Yasser A. Selim
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How to cite


Fadda, A.; Refat, H.; Kamal, S. Eur. J. Chem. 2014, 5(2), 296-304. doi:10.5155/eurjchem.5.2.296-304.1001
Fadda, A.; Refat, H.; Kamal, S. Utility of thiocarbamoyl moiety in synthesis of some new sulphur containing heterocyclic compounds and evaluation of their antimicrobial activity. Eur. J. Chem. 2014, 5(2), 296-304. doi:10.5155/eurjchem.5.2.296-304.1001
Fadda, A., Refat, H., & Kamal, S. (2014). Utility of thiocarbamoyl moiety in synthesis of some new sulphur containing heterocyclic compounds and evaluation of their antimicrobial activity. European Journal of Chemistry, 5(2), 296-304. doi:10.5155/eurjchem.5.2.296-304.1001
Fadda, Ahmed, Hala Refat, & Shimaa Kamal. "Utility of thiocarbamoyl moiety in synthesis of some new sulphur containing heterocyclic compounds and evaluation of their antimicrobial activity." European Journal of Chemistry [Online], 5.2 (2014): 296-304. Web. 1 Dec. 2020
Fadda, Ahmed, Refat, Hala, AND Kamal, Shimaa. "Utility of thiocarbamoyl moiety in synthesis of some new sulphur containing heterocyclic compounds and evaluation of their antimicrobial activity" European Journal of Chemistry [Online], Volume 5 Number 2 (30 June 2014)

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DOI Link: https://doi.org/10.5155/eurjchem.5.2.296-304.1001

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