European Journal of Chemistry 2014, 5(2), 356-362. doi:10.5155/eurjchem.5.2.356-362.1022

Synthesis of pyrazole, 1,3-dithiolan and thiophene derivatives pendant to thiazolo[2,3-c]-1,2,4-triazole moiety


Samia Mohamed Sayed (1) , Mohamed Ali Khalil (2) , Mohamed Abd-Elmonem Raslan (3,*)

(1) Chemistry Department, Faculty of Science, Aswan University, 81528 Aswan, Egypt
(2) Chemistry Department, Faculty of Science, Aswan University, 81528 Aswan, Egypt
(3) Chemistry Department, Faculty of Science, Aswan University, 81528 Aswan, Egypt
(*) Corresponding Author

Received: 25 Jan 2014, Accepted: 04 Mar 2014, Published: 30 Jun 2014

Abstract


Coupling of 5-acetyl-2-amino-4-methylthaizole diazonium sulphate (1) with 3-chloro-pentane-2,4-dione (2) afforded the thiazolo[2,3-c]-1,2,4-triazole derivative, (5). Bormination of compound (5) followed by reaction with potassium cyanide afforded bis-3-oxo-propanenitrile derivative (7) which, reacts with CS2/NaH/CH3I to afford the ketene S,S-dithioacetal, (8). Synthesis of 1,3-dithiolane (11) and thiophene (15) derivatives have been reported.


Keywords


Thiophene; 1,3-Thiazole; 1,3-Dithiolane; S,S-Dithioacetal; 3-Oxopropanenitrile; Thiazolo[2,3-c]-1,2,4-triazole

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DOI: 10.5155/eurjchem.5.2.356-362.1022

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Citations

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[1]. Mohamed A. Raslan, Samia M. Sayed, Mohamed A. Khalil
Reactivity of 2-(1-Methyl-1H-benzo[d]imidazol-2-yl)-2-nitrosoacetonitrile: A Facile One-Pot Synthesis of Benzimidazo[1,2-a]piperazine Derivatives
HETEROCYCLES  91(4), 824, 2015
DOI: 10.3987/COM-14-13160
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[2]. Mohamed A. Raslan, Omran A. Omran
Synthesis and Reactivity of Enaminones: Synthesis of Some 1,3,4-Thiadiazole Linked to Pyrazole, Pyridine, Benzimidazolopyrimidine, Pyrazolopyrimidine, Pyrazolotriazine and Triazolotriazine Derivatives
Journal of Heterocyclic Chemistry  53(4), 1121, 2016
DOI: 10.1002/jhet.2359
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[3]. Kamal M. Dawood, Samia M. Sayed
Synthesis and Reactivity of Enaminones: A Facile Synthesis of Thiophene and 1,3,4-Thiadiazole Derivatives Incorporating a Thiazole Moiety
Journal of Heterocyclic Chemistry  53(6), 1950, 2016
DOI: 10.1002/jhet.2512
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[4]. Samia M. Sayed, Mohamed A. Raslan, Mohamed A. Khalil
Synthesis and Reactivity of Cyanomethyl Thiazolyl Ketone: A Facile Synthesis of Some New Azoles, Chromene, Pyridine, Thiophene, Pyrazolo[3,4-b]pyridine and Pyrimido[1,2-a]benzimidazole Derivatives
HETEROCYCLES  91(3), 610, 2015
DOI: 10.3987/COM-15-13169
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[5]. Omran A. Omran, Samia M. Sayed, Mohamed A. Raslan
Iminophosphoranes in Heterocyclic Synthesis: A Facile Synthesis of Pyrido[4,3-D]Pyrimidine and Pyrido[4,3-D][1,3]Oxazine Derivatives via Intermolecular aza-Wittig Reactions
Journal of Heterocyclic Chemistry  54(2), 1103, 2017
DOI: 10.1002/jhet.2680
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[6]. Kamal M. Dawood, Samia M. Sayed, Mohamed A. Raslan
Synthesis of Pyrazolo[1,5-a ][1,3,5]triazine, Pyrazolo[1,5-a ]pyrimidine, and Imidazo[1,2-b ]pyrazole Derivatives Based on Imidazo[2,1-b ]thiazole Moiety
Journal of Heterocyclic Chemistry  54(4), 2405, 2017
DOI: 10.1002/jhet.2836
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[7]. Mohamed A. Khalil, Mohamed A. Raslan, Samia M. Sayed
Synthesis and Reactivity of 3-oxoprop-1-en-1-olate Derivative as a Building Block for the Synthesis of Azole and Azine Derivatives
Journal of Heterocyclic Chemistry  54(3), 1845, 2017
DOI: 10.1002/jhet.2775
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[8]. Mohamed A. Raslan, Samia M. Sayed, Mohamed A. Khalil
Synthesis of Some Pyrazole, Thiazole, Pyridine, and 1,3,4-Thiadiazole Derivatives Incorporating 2-Thiazolyl Moiety
Journal of Heterocyclic Chemistry  53(3), 727, 2016
DOI: 10.1002/jhet.2335
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How to cite


Sayed, S.; Khalil, M.; Raslan, M. Eur. J. Chem. 2014, 5(2), 356-362. doi:10.5155/eurjchem.5.2.356-362.1022
Sayed, S.; Khalil, M.; Raslan, M. Synthesis of pyrazole, 1,3-dithiolan and thiophene derivatives pendant to thiazolo[2,3-c]-1,2,4-triazole moiety. Eur. J. Chem. 2014, 5(2), 356-362. doi:10.5155/eurjchem.5.2.356-362.1022
Sayed, S., Khalil, M., & Raslan, M. (2014). Synthesis of pyrazole, 1,3-dithiolan and thiophene derivatives pendant to thiazolo[2,3-c]-1,2,4-triazole moiety. European Journal of Chemistry, 5(2), 356-362. doi:10.5155/eurjchem.5.2.356-362.1022
Sayed, Samia, Mohamed Ali Khalil, & Mohamed Abd-Elmonem Raslan. "Synthesis of pyrazole, 1,3-dithiolan and thiophene derivatives pendant to thiazolo[2,3-c]-1,2,4-triazole moiety." European Journal of Chemistry [Online], 5.2 (2014): 356-362. Web. 21 Oct. 2019
Sayed, Samia, Khalil, Mohamed, AND Raslan, Mohamed. "Synthesis of pyrazole, 1,3-dithiolan and thiophene derivatives pendant to thiazolo[2,3-c]-1,2,4-triazole moiety" European Journal of Chemistry [Online], Volume 5 Number 2 (30 June 2014)

DOI Link: https://doi.org/10.5155/eurjchem.5.2.356-362.1022

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