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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 40, 2010 - Issue 9
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Original Articles

Synthesis and Reactions of Some Novel Nicotinonitrile, Thiazolotriazole, and Imidazolotriazole Derivatives for Antioxidant Evaluation

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Pages 1360-1370 | Received 26 Apr 2009, Published online: 07 Apr 2010
 

Abstract

The novel 2-(1H)-pyridone, the lead compound of the pyridone derivative 1, reacted with an electrophilic reagent (ethyl chloroacetate) to give the corresponding ester 2. Condensation of compound 2 with thiosemicarbazide and/or hydrazine hydrate afforded the mercaptotriazole and the corresponding acetic acid hydrazide derivatives 3 and 4, respectively. The latter compound reacted with ethyl acetoacetate, ethyl cyanoacetate, and maleic anhydride to give compounds 5, 6, and 7, respectively. Alkylation of compound 3 with methyl iodide or chloroacetic acid afforded methylsulfanyltriazole and thiazolotriazole derivatives 8 and 9, respectively. Compound 8 reacted with glycine to afford the imidazotriazole derivative 10. Both compounds 9 and 10 reacted with glucose and benzaldehyde to give compounds 11, 12, 13, and 14, respectively. Some of the prepared products were selected and subjected to screening for their antioxidant activity.

ACKNOWLEDGMENT

We are thankful to Dr. Sahar R. Abd El-Hamid, Medicinal and Aromatic Plants Department, National Research Center, for antioxidant evaluation.

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