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Paper | Regular issue | Vol 92, No. 4, 2016, pp.649-663
Published online, 26th February, 2016
DOI: 10.3987/COM-15-13370
■ Synthesis of Some Novel Thiadiazoles and Thiazoles Linked to Pyrazole Ring

Magda A. Abdallah, Sobhi M. Gomha,* Mohamad R. Abdelaziz, and Nany S. Eldin Serag

*Department of Organic Chemistry, Cairo University, Giza-Haram 12613, Egypt

Abstract

The novel compound namely ethyl 3-(1-(2-(2-cyanoacetyl)- hydrazono)ethyl)-1,5-diphenyl-1H-pyrazole-4-carboxylate 3 was used as key intermediate for synthesizing the thioanilide derivative 4 and the arylidene derivatives 6. The reaction of 4 with a number of haloketones and haloesters furnished the respective thiazole derivatives 8, 10 and 11a,b. Moreover, the reaction of 4 with N-aryl-2-oxopropane hydrazonoyl chloride 13 and ethyl (N-arylhydrazono)chloroacetate 17 in absolute ethanol in the presence of triethylamine at reflux afforded a new series of thiadiazoles 15 and 19, respectively. The mechanisms that account for formation of products 15 and 19 were discussed. Also, the structures of all the newly synthesized products were confirmed based on elemental analysis, spectral data and by alternative methods.