Fluorinated Triazoles and Tetrazoles

Regioselective Synthesis of 5-Trifluoromethyl 1,2,4-Triazoles via [3 + 2]-Cycloaddition of Nitrile Imines with CF3CN

“…Among these 1,2,4-triazoles, trifluoromethylated 1,2,4-triazoles have attracted significant attention [ 8 ]. It has been well established that the introduction of trifluoromethyl into therapeutic compounds can impart beneficial effects to lipophilicity, metabolic stability, conformational preference, and bioavailability [ 9 , 10 , 11 ].…”

Regioselective synthesis of 3-trifluoromethyl 1,2,4-triazoles via photocycloaddition of sydnone with CF3CN

“…5 Among these compounds, perfluoroalkylated 1,2,4-triazoles hold a particular significance in organic synthesis because of their ubiquitous presence in synthetic pharmaceuticals, agrochemicals, and storage materials. 6 3-Triazolylphenylsulfides were used as insecticides, acaricides, and nematicides; 7 sitagliptin is a dipeptidyl peptidase-4 inhibitor used in the management of Type II diabetes in adults. 8 This is probably due to the introduction of perfluoroalkyl groups into organic molecules altering their chemical and physical properties including electronegativity, lipophilicity, solubility, metabolic stability, and bioavailability.…”

Straightforward access to fluoroalkyl tetrazoles from fluoroalkylN-sulfonylhydrazones

“…3 Specifically, tetrazoles represent a remarkable class of commonly found core-azoles in a vast plethora of molecules with medical or biochemical applicability; however, very few examples of preparations of fluoroalkyl tetrazoles have been disclosed until now. 4,5 Classic methods for preparing aryl tetrazoles relied primarily on the cycloadditions of azide reagents with nitriles or imidoyl derivatives; 6 however, only CF 3 -tetrazoles could be obtained by this route. 7 Moreover, the toxicity and explosivity risk of azides predominantly hindered their synthetic applications.…”