The Chemical and Structural Properties of 2-Aminobenzylamine Derivatives

Abstract

We report a conventional and simple method to synthesize quinazoline and benzodiazepine derivatives by treatment of 2-aminobenzylamine (1) with several p-electron-deficient compounds. Quinazoline derivatives were obtained by treatment of 1 with either tetracyanoethylene or 7,7,8,8-tetracyanoquinodimethane. Benzodiazepine derivatives were formed when 1 was reacted with either 2,3- dichloro-1,4-naphthoquinone or 2,3-dichloro-5,6-dicyano-1,4-benzoquinone. Fused quinazoline and benzoazepine derivatives were formed by dry heating of 1 with either naphthalic anhydride, cis- 1,2,3,6-tetrahydrophthalic anhydride, tetrachlorophthalic anhydride and/or diphenic anhydride, respectively. The NMR spectra and the mass spectrometric data as well as elemental analyses of all new products are consistent with the proposed structures. The structures of the quinazoline derivatives 26 and 28 were further confirmed by single-crystal X-ray structure determination. Plausible mechanisms for the formation of several products are discussed.