Studying the reactivity of N-2-(2-aminobenzoyl)-N-phenyl-hydrazinecarbothioamide toward some selected carbonyl compounds

The reactivity of N-2-(2-aminobenzoyl)-N-phenylhydrazinecarbothioamide (1) as an electron donor toward several electron-accepting compounds through electron donor-acceptor interaction has been studied. Thus, upon treatment of 1 with either 1,4-naphthoquinone, 2-dicyanomethyleneindan-1,3-dione, or 2,3-dichloro-1,4-naphthoquinone, the reaction proceeds to give thiadiazino[5,4-b]quinazoline, N-phenylcarbamohydrazonothioate, and thiadiazine-5,10-dione, respectively. Also, the reactivity of compound 1 toward some aldehydes and anhydrides was studied. The products were fully characterized by their spectral data. The mechanisms of formation of the products have been rationalized.