Letters in Organic Chemistry

Author(s): Neha Rani, Deepak K. Aneja*, Mayank Kinger*, Rinku Soni, Monika Sihag, Sandeep Malik and Kirti Bhardwaj

DOI: 10.2174/0115701786332586240819074232

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An Efficient Metal-Free Methodology for the Synthesis of Hydrazo-Linked 5-(4-aryl)-1H-1,2,4-Triazoles

Page: [334 - 341] Pages: 8

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Abstract

Hydrazo compounds have displayed significant roles in both biological and physical aspects, such as spinamycin as a potent growth inhibitor against fungi and rat sarcoma cells, hydrazo tocopherol as a component of vitamin E, and electron-rich hydrazo-linked triazines as energetic materials. In this study, a metal-free approach was proposed for the synthesis of hydrazo-linked 5-(4- aryl)-1H-1,2,4-triazoles. The methods for the synthesis of 5-(4-aryl)-1H-1,2,4-triazoles initiated by the reaction of aldehyde with semicarbazide. The resulted compound, 5-(4-aryl)-1H-1,2,4-triazol-3- ol, upon reaction with phosphorous oxychloride yielded 3-chloro-5-(4-aryl)-1H-1,2,4-triazoles. These synthesized compounds upon fusión with various aryl and hetero aryl substituted hydrazines provided desired hydrazo moieties. Synthesized hydrazo compounds were characterized by spectroscopic techniques, viz. 1H-NMR, FT-IR and mass spectrometry. In this study, a series of novel hydrazo- linked 5-(4-aryl)-1H-1,2,4-triazoles were synthesized. The methodology proposed in this study eliminates the use of complicated procedures and heavy metals.

Keywords: Heterocycles, triazole, reflux, hydrazine hydrate, hydrazide, semicarbazide, hydrazo compounds.