Azide–acetonitrile “click” reaction triggered by Cs₂CO₃: the atom-economic, high-yielding synthesis of 5-amino-1,2,3-triazoles

Abstract

A Cs 2 CO 3 -catalyzed azide-acetonitrile [3+2]-cycloaddition reaction of monosubstituted acetonitriles with aryl azides has been developed for the synthesis of 5-amino-1,2,3-triazoles.

Advancement of the 5-Amino-1-(Carbamoylmethyl)-1H-1,2,3-Triazole-4-Carboxamide Scaffold to Disarm the Bacterial SOS Response

“…Three sets of reagents that have been previously reported to facilitate such cyclizations were screened: stoichiometric sodium methoxide (Alfred, 1970; L’abbé and and Beenaerts, 1989; Julino and Stevens, 1998), stoichiometric sodium ethoxide (Hoover and Day, 1956; Livi et al, 1979), and catalytic cesium carbonate (Krishna et al, 2015). In most cases the choice of base between stoichiometric sodium ethoxide and catalytic cesium carbonate had little to no impact on the yield (e.g., 1 , Table 1).…”

Click polymerization: The aurora of polymer synthetic methodology

“…However, carbon‐nitrogen triple‐bonds based click polymerization is another attracting research direction because the organic reactions have been reported. For example, the azide‐acetonitrile click reaction was reported and 5‐amino‐1,2,3‐triazoles could be generated . In addition, a new highly efficient silver catalyzed click reaction of terminal alkynes and isocyanides was presented in the literature .…”

One‐Pot Synthesis of 5‐Amino‐1,2,3‐triazole Derivatives via Dipolar Azide−Nitrile Cycloaddition and Dimroth Rearrangement under Solvent‐Free Conditions

“…Biologically active 1,2,3‐triazoles primarily include 1,4‐disubstituted 5‐amino 1,2,3‐triazoles [10] and 5‐alkyl(aryl)amino derivatives of 1,2,3‐triazole [11] . The presence of an amino group at position 5 is often responsible for the manifestation of the maximum biological activity [6,12] .…”