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

[ Vol. 19 , Issue. 3 ]

Author(s):

T. M. Vishwanatha, N. Narendra and Vommina V. Sureshbabu   Pages 308 - 314 ( 7 )

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.

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

Affiliation:

Department of Studies in Chemistry, Central College Campus, Bangalore University, Dr. B. R. Ambedkar Veedhi, Bangalore -560 001, India.



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