Synthesis and Characterization of Several Mannich Bases Derived from 2-(4-methylpiperazin-1-yl)acetohydrazide

Abstract

This study explores the transformation of 2-(4-methylpiperazin-1-yl)acetohydrazide (1) through its reaction with phenylisothiocyanate (2), resulting in the formation of a novel urea derivative (3). The synthesis involves an intramolecular ring closure, where the hydrazide functionality plays a crucial role, leading to the formation of a 1,2,4-triazole structure. The journey continues as the 1,2,4-triazole derivative undergoes a Mannich reaction, leveraging its active methylene group. By reacting Compound 3 with formaldehyde and a selection of primary or secondary amines, a β-aminocarbonyl compound is synthesized, showcasing a significant molecular transformation. The structural elucidation of the synthesized compounds is carried out using a range of sophisticated analytical techniques, including mass spectrometry, infrared (IR) spectroscopy, and nuclear magnetic resonance (NMR) spectroscopy for both ¹H and ¹³C nuclei. These methods provide deep insights into the molecular architecture, enabling the determination of atomic connectivity and the identification of functional groups, thus confirming the integrity and structure of the synthesized molecules