The synthesis and crystal structure of 2-[4(S)-4,5-dihydro-4-phenyl-2-oxazolinyl]-benzenamine, and 2-[4(S)-4,5-dihydro-4-benzyl-2-oxazolinyl]-benzenamine

Two oxazolines compound 1a and 1b, 2-4(S)-4,5-dihydro-4-phenyl-2-ozazolinyl-benzenamine, and (C₁₅H₁₄N₂O), 2-4(S)-4,5-dihydro-4-benzyl-2-ozazolinyl-benzenamine (C₁₆H₁₆N₂O) were obtained in moderate yield from the reactions of 2-aminobenzonitrile with optically active L-(+)-Phenylglycinol and L-(+)-Phenylalaninol, respectively, in chlorobenzene under dry, anaerobic conditions. ZnCl₂ was dried under vacuum and acted as a Lewis acid catalyst in this reaction. The structures of 1a and 1b were determined by X-ray diffraction and NMR. There exist intra- and intermolecular N-H…N hydrogen bonds in the crystal structure.