Design, green synthesis and reactions of 2,3-dioxo-1,2,3,4-tetrahydroquinoxaline-6 sulfonohydrazide derivatives

Abstract

2,3-Dioxo-1,2,3,4-tetrahydroquinoxaline-6-sulfonohydrazide and its derivatives were synthesized and characterize by IR, 1 H-NMR, 13 C-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.