title: CuI-promoted one-pot synthesis of N-Boc protected β-ketotriazole amino acids: application in the synthesis of new class of dipeptidomimetics.
abstract: One-pot click chemistry of N(α)-Boc-bromomethylketones, NaN3 and propiolic acid affords N-Boc protected 1,4-disubstituted 1,2,3-β-ketotriazole acids in good to excellent yield. The use of CuI as catalyst and DMSO as solvent leads the click reaction to efficient, practical and column-free preparation of the title compounds. The utility of the resulting unnatural amino acids as building blocks to prepare triazole possessing peptidomimetics is also delineated.
authors.affiliation: Department of Studies in Chemistry, Central College Campus, Bangalore University, Bangalore, India.
authors.forename: T M
authors.initials: TM
authors.lastname: Vishwanatha
authors.forename: N
authors.initials: N
authors.lastname: Narendra
authors.forename: Vommina V
authors.initials: VV
authors.lastname: Sureshbabu
mesh_terms: D000596:Amino Acids / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D060326:Chemistry Techniques, Synthetic / Q000379:methods*; D057930:Click Chemistry; D003300:Copper / Q000737:chemistry*; D004151:Dipeptides / Q000737:chemistry*; D005563:Formic Acid Esters / Q000737:chemistry*; D007454:Iodides / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry; D057786:Peptidomimetics / Q000138:chemical synthesis* / Q000737:chemistry; D013696:Temperature; D014230:Triazoles / Q000737:chemistry*
chemical_list: D000596:Amino Acids; D004151:Dipeptides; D005563:Formic Acid Esters; D007454:Iodides; D007659:Ketones; D057786:Peptidomimetics; D014230:Triazoles; C000345:t-butyloxycarbonyl group; D003300:Copper; C073870:cuprous iodide