Functionally substituted arylhydrazones as building blocks in heterocyclic synthesis: Facile synthesis of pyrazoles, triazoles, triazines and quantum chemical studies

Abstract

The arylhydrazones were treated with ethyl iodide, ethyl chloroacetate to afford the alkyl derivatives, which cyclized to the pyrazole derivatives, also, arylhydrazones were reacted with ethyl chloroformate to furnish the triazindione derivative. Reactions of arylhydrazones with hydroxylamine hydrochloride afforded the oxime derivative. Treatment of arylhydrazones with binucleophile reagents such as hydrazine hydrate and phenyl hydrazine gives the pyrazole derivatives. Treated of arylidine derivatives with malononitrile and hydrazine hydrate afforded the 4H-pyrane derivatives and pyrazole derivatives. The theoretical calculations optimization and frequency of synthesized compounds by Gaussian 09 with DFT by B3LYP method. The base set 6–31 G (d,p) to obtain descriptors explains the reactivity or stability of the synthesized compounds. It predicts the relation between theoretical descriptors computed which agree with experimental data.

Graphical Abstract

Keywords:

• Arylhydrazones
• DFT calculation
• pyrazoles
• triazines
• triazoles

Acknowledgments

The authors would like to thank the Chemistry Department, Faculty of Science, Al-Azhar University at Assiut for their financial support to facilitate the publication of this study.

Disclosure statement

No potential conflict of interest was reported by the author(s).