CuI-Promoted One-Pot Synthesis of N-Boc Protected β-Ketotriazole Amino Acids: Application in the Synthesis of New Class of Dipeptidomimetics

Title: CuI-Promoted One-Pot Synthesis of N-Boc Protected β-Ketotriazole Amino Acids: Application in the Synthesis of New Class of Dipeptidomimetics

Volume: 19 Issue: 3

Author(s): T. M. Vishwanatha, N. Narendra and Vommina V. Sureshbabu

Affiliation:

Keywords: Nα-Boc-bromomethylketones, one-pot click chemistry, CuI, N-Boc-protected 1,4-disubstituted 1,2,3β-ketotriazole, N-Boc-protected 1,4-disubstituted 1,2,3β-ketotriazole amino acids, amino acids, peptidomimetics, nanotubes, halides, dimethylacetylenedicarboxylate, triazole

Abstract: One-pot click chemistry of Nα-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.

Cite this article as:

M. Vishwanatha T., Narendra N. and V. Sureshbabu Vommina, CuI-Promoted One-Pot Synthesis of N-Boc Protected β-Ketotriazole Amino Acids: Application in the Synthesis of New Class of Dipeptidomimetics, Protein & Peptide Letters 2012; 19 (3) . https://dx.doi.org/10.2174/092986612799363172