English

O Taiwo Festus,A Obafemi Craig

doi:10.5897/ijps2016.4548

Abstract

2,3-Dioxo-1,2,3,4-tetrahydroquinoxaline-6-sulfonohydrazide and its derivatives were synthesized and characterize by IR, 1H-NMR, 13C-NMR and mass spectrometry analytical methods. The 2,3-dioxo-1,2,3,4-tetrahydroquinoxaline-6-sulfonyl hydrazide (compound 1), was synthesized from the reaction of o-phenylenediamine with oxalic acid to obtain quinoxaline-2,3-dione, which was subjected to chlorosulfonation with chlorosulfonic acid to give 2,3-dioxo-1,2,3,4-tetrahydroquinoxaline-6-sulfonyl chloride. The 2,3-dioxo-1,2,3,4-tetrahydroquinoxaline-6-sulfonyl chloride was reacted with hydrazine hydrate to afford 2,3-dioxo-1,2,3,4-tetrahydroquinoxaline-6-sulfonyl hydrazide (compound 1). The quinoxaline-6-sulfonohydrazone derivatives were synthesized by reacting compound 1 with substituted benzaldehydes or aromatic ketones. The chemical structures of the compounds prepared were confirmed by spectral data. The synthetic methodology was efficient and environmentally friendly; this was due to the fact that the work-up stage was carried out in water. Key words: 2,3-Dioxo-1,2,3,4-tetrahydroquinoxaline-6-sulfonyl hydrazide, quinoxaline-2,3-dione, synthesis, substituted benzaldehydes, isatin, infrared, spectroscopy.

Highlights

Heterocyclic compounds represent an important class of biologically active molecules (Sakata et al, 1998; Michael et al, 2002; Jaso et al, 2003; Zeb et al, 2014)
Many techniques have been employed in the synthesis of hydrazone frameworks (Sridharan et al, 2007; AbdElhafez et al, 2003; Vicini et al, 2003; Sridhar Ramesh, 2001; Beheshtiha et al, 2010; Asegbeloyin et al, 2015) and quinoxaline moieties
Sulfonohydrazide 1 was synthesized starting from the reaction of 1,2,3,4-tetrahydroquinoxaline-2,3-dione with excess chlorosulfonic acid to obtain the corresponding

Summary

Introduction

Heterocyclic compounds represent an important class of biologically active molecules (Sakata et al, 1998; Michael et al, 2002; Jaso et al, 2003; Zeb et al, 2014). Hydrazone containing azomethine-NHN=CH protons constitutes an important class of compounds for novel drug development (Rollas and Kuçukguzel, 2007; Kaurase et al, 2011). It plays an essential role in biologically active compounds (Rangisetty et al, 2001; Salgin-Goksen et al, 2007; Ragavendran et al, 2007; Mehta et al, 2006; Bijev, 2006) and represents an interesting template for medicinal chemistry (Rowan et al, 2002; Chang et al, 2003; Dongsheng et al, 2014).

Methods

Results

Conclusion