Synthesis, Characterization and Biological activity of Novel Tetrazole Compounds Derived from Azo Schiff bases

Abstract

Tetrazole and its derivatives are one of the most common five-membered heterocyclic compounds that receive great attention from researchers. Their importance is due to their multiple applications in various fields, such as industrial, medical, and agricultural applications. The aim of the current study is to obtain a new nucleus for the active compound 4- aminoantipyrene with an active group, which is the formyl group, then link it with different amines to form compounds (Schiff bases) that contain the active group ( C=N ) azomethine and convert them to the heterogeneous pentacyclic system called tetrazoles which is expected to have promising biological effectiveness. In this study, (E)-3-((1,5-dimethyl-3-oxo-2-phenyl-2,3-dihydro-1H-pyrazol-4-yl) diazenyl)-4-hydroxybenzaldehyde (AZ1) was prepared by the reaction of 4-aminoantipyrine Diaz onium salts and 4- hydroxybenzaldehyde under base conditions. Schiff bases (2-6) were synthesized by the condensation of compound (1) and aromatic amines such as (4-aminoaniline, , 3-nitroaniline, 4-amino pyridine, 4-aminoantipyrin and 2,4-dinitroaniline). A novel of five member-rings of Tetrazoles (A₇-A₁₁) were created through the interaction of Schiff bases and sodium azide. IR as well as NMR spectrum investigations validated the structure of the resulted compounds example (A10 and A5) compounds

A novel of five member-rings of Tetrazoles  (A₇-A₁₁) were created through the interaction of Schiff bases and sodium azide. IR as well as NMR spectrum investigations validated the structure of the resulted compounds example (A10 and A5) compounds