Preparation of Optically Active Amino Acid Derivatives of Some Methylated 5-Amino-Azaheterocycles

Authors: MASHOODA HASAN, FARZANA SHAHEEN, UZMA YUNUS, SHAZIA MUNIR

Abstract: The present paper describes the reduction of 1-methyl-5-nitro-benzimidazoles ({\bf 1A, 2A}) and 1,3-dimethyl-2H-5-nitro-benzimidazol-2-one ({\bf 3}) to 5-aminobenzimidazoles ({\bf 4A, 5A}) and 1,3-dimethyl-2H-5-amino-benzimidazol-2-one ({\bf 6}) respectively with hydrazine hydrate in absolute ethanol in the presence of graphite. Compounds {\bf 5A} and {\bf 6} were converted to 2-ethyl-5-(phthaloyl-L-phenylalanyl)amino-1-methylbenzimidazole ({\bf 7}) and 1,3-dimethyl-5-(phthaloyl-L-phenylalanyl)aminobenzimidazol-2-one ({\bf 8}). Characterization of the synthesized compounds was done with the help of mass spectrometry and ^1H NMR spectroscopic studies. Optical activity of the amino acid derivatives {\bf 7} and {\bf 8} was also recorded.

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