Synthesis of 4'-nitrophenyl-2-aminobenzthiazol-6-yl sulfides and 4' nitrophenyl-2-aminobenzthiazol-6-yl sulfones containing dithiocarbamate

Abstract

2-Amino-6-[(p-nitrophenyl)thio]benzthiazol (1) reacted with carbon disulfide in the presence of concentrated aqueous sodium hydroxide and with N. N'-dimethylformamide as solvent, to form the sodium salt of dithiocarbonimidic acid. This compound was reacted without further purification with one mole of methyl iodide to give monoalkylated product (2). Reaction with two moles of methyl iodide gave the dialkylated product (3). Reaction of (2) with anthranilic acid yielded 2-(2, 3-dihydro-2-thioxo-4(lH) quinoxalinon-3-yl)-6-[(p-nitrophenyl)thio)benzthiazol (4). Reaction of (3) with o-phenylene diamine gave 2-(2-benzimidazolylamino)-6-[(p-nitrophenyl)thio]-benzthiazole (5), and reaction of (3) with potassium salt of anthranilic acid gave 2-(2-imino benzoxazine)-6-[(p-nitrophenyl)thio]benzthiazol (6). (6) was condensed with a range of aromatic amine to form the 3-arylquinazolinones (7, a-d). Oxidation of compounds (4-7) using H202 in glacial acetic acid afforded the corresponding diaryl sulfones (8-11). © 1990, Taylor & Francis Group. All rights reserved.