ChemInform Abstract: Desulfurization of 4-Nitro-N,2-diphenyl-3-(phenylamino)isothiazol-5(2H)-imine: Formation of a 3-Imino-2-nitroprop-2-enamidine.

✍ Scribed by Dally Moya Argilagos; Roland W. Kunz; Anthony Linden; Heinz Heimgartner

• Publisher: John Wiley and Sons
• Year: 2010
• Weight: 32 KB
• Volume: 30
• Category: Article
• ISSN: 0931-7597
• DOI: 10.1002/chin.199916066

✦ Synopsis

Desulfurization of 4-Nitro-N,2-diphenyl-3-(phenylamino)isothiazol-5(2H)-imine:

Formation of a 3-Imino-2-nitroprop-2-enamidine. -Desulfurization of the title isothiazolimine (I) is proposed to afford an imino(nitro)propenamidine intermediate (XI) which can be trapped by reaction with several nucleophiles. Thus, with amines (II) the corresponding amidine derivatives (III) are formed, while thiophenol (IV) reacts with formation of thioimidate (V). The reaction with benzoic and thiobenzoic acid affords by attack at the ketene carbon analogous products which, however, undergo a further acylation [to furnish compound (VII)] or hydrolysis [to give amidine (VIII)]. The reaction of the amidine intermediate with benzylidene(methyl)amine (IX) proceeds by addition to the nitro group and elimination of phenyl isocyanate to give oxadiazole derivative (X). The reactivity of the nucleophiles toward the amidine intermediate is shown to be determined not only by their nucleophilicity but also by their acidity.