European Journal of Chemistry 2014, 5(2), 296-304. doi:10.5155/eurjchem.5.2.296-304.1001

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, Accepted: 28 Jan 2014, Published: 30 Jun 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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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
DOI: 10.1002/jhet.3536
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[2]. Elsherbiny H. El-Sayed, Ahmed A. Fadda
Synthesis and Antimicrobial Activity of Some Novel bis Polyfunctional Pyridine, Pyran, and Thiazole Derivatives
Journal of Heterocyclic Chemistry  55(10), 2251, 2018
DOI: 10.1002/jhet.3276
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[3]. 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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[4]. 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
DOI: 10.3987/COM-15-13370
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[5]. 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
DOI: 10.1007/s13738-014-0547-y
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[6]. Ahmed A. Fadda, Eman H. Tawfik, Yasser A. Selim
Synthesis and Biological Evaluation of Some New Thiophene, Thiazole, Dithiolane Derivatives and Related Compounds
Polycyclic Aromatic Compounds  , 1, 2018
DOI: 10.1080/10406638.2018.1555174
/


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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. 23 Oct. 2019
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)

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

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