title: Asymmetric synthesis of novel (1H-benzo[d]imidazol -2-ylthio)- and (di-n-butylamino-2-ylthio)acetamides.
abstract: Asymmetric synthesis of novel (1H-benzo[d]imidazol-2-ylthio)- and (di-n-butylamino)acetamides is described. The o-nitrobenzyl oxime ethers were reduced with borane in the presence of oxazaborolidenes derived from norephedrine or diphenylvalinol and diphenylphosphinic amide was reduced with modified sodium tetrahydroborate catalyzed with beta-ketoiminato cobalt(II) complex to the corresponding amines with high yields and moderate enantiomeric excess. Reaction of amines with 2-chloroacetyl chloride and next with thiobenzimidazole or n-dibutylamine gave corresponding products with high yields.
authors.affiliation: Faculty of Pharmacy, Department of Chemical Technology and Pharmaceuticals, Nicolaus Copernicus University, 2 A. Jurasza St., 85-089 Bydgoszcz, Poland. krzysztof.laczkowski@cm.umk.pl
authors.forename: Krzysztof Z
authors.initials: KZ
authors.lastname: Łaczkowski
mesh_terms: D000081:Acetamides / Q000138:chemical synthesis*; D001880:Boranes / Q000737:chemistry; D002384:Catalysis; D004987:Ethers / Q000138:chemical synthesis; D007093:Imidazoles / Q000138:chemical synthesis*; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010091:Oximes / Q000138:chemical synthesis
chemical_list: D000081:Acetamides; D001880:Boranes; D004987:Ethers; D007093:Imidazoles; D010091:Oximes