Isothioureas, Ureas, and Their N-Methyl Amides from 2-Aminobenzothiazole and Chiral Amino Acids.

摘要: In this investigation, the reaction of 2-dithiomethylcarboimidatebenzothiazole with a series six chiral amino-acids was studied. The proceeds through isolable sodium salt SMe-isothiourea carboxylates as intermediates, whose methyl iodide in stirring DMF solvent affords esters. presence water leads to corresponding urea esters were obtained. Finally, N-methyl amide derivatives isolated when or reacted methylamine water. structures synthesized compounds established by 1H and 13C nuclear magnetic resonance derived from (l)-glycine, (l)-alanine, (l)-phenylglycine, (l)-leucine, X-ray diffraction analysis. This methodology allows functionalize 2-aminobenzothiazole SMe-isothiourea, urea, methylamide groups amino acids get benzothiazole containing coordination sites hydrogen bonding groups. Further research on biological activities some these is ongoing.