Synthesis of Some Novel 1-(Substituted Phenyl)-2-(4-(Trimethylsilyl)-1H-1,2,3-Triazol-1-YL) Ketones

GRAPHICAL ABSTRACT

R: substituted phenyl, R₁: H, CH₃.

Abstract

A facile and highly efficient method for the regioselective one-pot synthesis of a series of novel 1-(substituted phenyl)-2-(4-(trimethylsilyl)-1H-1,2,3-triazol-1-yl)ketones from 2-bromo-1-(substituted phenyl)ketones, sodium azide, and trimethylsilyl acetylene, through Cu (I) catalyzed 1,3-dipolar [3+2] cycloaddition reaction is reported. The reaction proceeds smoothly in 40% aqueous acetone at room temperature without the use of any additive. Regioselectivity privileges the formation of the corresponding C-4 silylated-1,2,3-triazoles in high yields in all instances. The methodology offers an entry to new 1,2,3-triazolyl-4-trimethylsilyl anionic synthon scaffolds.

Keywords:

• [3+2] Cycloaddition
• copper (I) catalysis
• silylated-1,2,3-triazoles
• 2-bromo-1-(substituted phenyl)ketones

ACKNOWLEDGMENT

The authors are thankful to the NMR department, Indian Institute of Science-Bangalore for spectral analysis.