NITROGEN HETEROCYCLES IN MEDICINAL AND FUNCTIONAL APPLICATIONS: SYNTHESIS, CHARACTERIZATION AND DEVELOPMENT OF A TRIAMTERENE DERIVATIVE

Abstract

Nitrogen-containing heterocycles are an important class of organic compounds with broad applications in medicinal chemistry, pharmaceuticals, and materials science. Fused nitrogen-rich heterocyclic systems are of particular interest due to their diverse biological activities and favorable physicochemical properties. This study reports the synthesis of a novel triamterene-derived heterocycle, 2-phenylbenzopyrazino[2,3-g][1,8]naphthyridin-3,12-diamine, via a straightforward and cost-effective multistep process involving nitrosation, cyclization, and mild catalytic transformation. Reaction progress was monitored by thin-layer chromatography. The target compound was isolated as a pale-yellow crystalline solid in 78% yield, with a melting point of 115–118 °C. Structural characterization by FTIR, 1H NMR, 13C NMR, and ESI-MS confirmed the fused nitrogen-containing heterocyclic framework, including N–H, C=N, and C–N functionalities, and the expected molecular ion peak. The methodology offers excellent reproducibility and scalability, with minimal side product formation. These findings provide an efficient approach to structurally complex triamterene-based heterocycles with potential pharmaceutical applications.