Design and the synthesis of 1‐heteroaryl‐1,2,3‐triazoles connected to coumarins via ether linker

Abstract

In this paper, we report an efficient and versatile methodology for the synthesis of a series of novel heteroaryl‐1,2,3‐triazoles connected to 4‐methylcoumarin (4‐methyl‐2H‐chromen‐2‐one) via oxymethylene linker. The desired molecules were accessed by both two‐step synthesis and the one‐pot copper catalyzed cycloaddition reaction of heteroaromatic azides with coumarin containing acetylenes. The developed protocol was found to be facile and effective for preparing a series of novel heteroaryl‐1,2,3‐triazole‐coumarin conjugates in excellent yields. Practical utility of one‐pot protocol has been confirmed by the successful gram‐scale synthesis of 1,3‐Dimethyl‐6‐(4‐[([4‐methyl‐2‐oxo‐2H‐chromen‐7‐yl]oxy)methyl]‐1H‐1,2,3‐triazol‐1‐yl)pyrimidine‐2,4(1H,3H)‐dione.

Mechanochemical approach towards multi-functionalized 1,2,3-triazoles and anti-seizure drug Rufinamide analogs using copper beads

“…The 1,2,3-triazole moiety represents one of the versatile classes of heterocycles because of their widespread applications as pharmaceutical agents, agrochemicals, biochemicals and polymers [1][2][3][4][5][6][7][8][9][10][11][12][13][14]. The seminal work on "click chemistry" by Huisgen, followed by the further independent development by Meldal et al and Sharpless-Fokin has encouraged extensive research on the 1,2,3-triazole molecule [15][16][17].…”

Synthesis of Biologically Relevant 1,2,3- and 1,3,4-Triazoles: From Classical Pathway to Green Chemistry

“…Triazoles have become increasingly popular between medicinal chemists and pharmaceutical companies due essentially to their unique properties such as: rigidity, strong hydrogen-bond properties, stability under in vivo, and interesting pharmacokinetic profiles. Due to their importance, much literature data exist for 1,2,3-triazole systems in comparison to the 1,2,4-triazoles concerning either their syntheses or their biological activities see for instance [ 53 , 54 , 55 ]. In that respect the review presented here focuses on three recent parts, namely: Construction of 1,2,3-triazole systems in biologically relevant compounds by means of classical and “green chemistry” conditions involving ultrasound chemistry and mechanochemistry.…”