Synthesis of 1H-1,2,4-Triazoles via Nitrilium Salts

Polyfluoroaromatic compounds with a NCClR group—a reactive type of polyfluoroarene

“…In this case, exchange of chlorine by fluorine occurs together with HF addition at the N C multiple bond, forming N-trifluoromethylpentafluoroaniline, which on dehydrofluorination is converted to the carbonimidoyl difluoride dimer [67,68]. Imidoyl chlorides 19,25,75,76,80 react with CsF at 160-170 8C or with KF at 250 8C, giving the corresponding imidoyl fluorides. The reaction with KF is less favoured, requires a higher temperature and occurs with a lower degree of conversion of the starting chloride [16,44].…”

“…The nitrilium salts formed from N-arylhydrazono chlorides under the action of AlCl 3 react with aliphatic or aromatic nitriles by a two-step cycloaddition involving the lone electron pair of the nitrile nitrogen, leading to 1,2,4-triazoles [76,77]. In the presence of AlCl 3, aromatic imidoyl chlorides with at least one vacant position ortho to the imidoyl chloride group in the N-aromatic ring, give nitrilium salts, which interact with aliphatic or aromatic nitriles forming quinazolines [78].…”

Computationally motivated synthesis and enzyme kinetic evaluation of N-(β-d-glucopyranosyl)-1,2,4-triazolecarboxamides as glycogen phosphorylase inhibitors

“…[40][41][42][43] The Fig. 3 The lowest solution phase energy pose of ligand 5a (tautomer t2) bound at GPb with a dihedral angle (u ¼ 19.7 ; Table 3), as calculated using QM/MM and described in the text.…”

Microwave-assisted synthesis of substituted 1,2,4-triazoles

“…Many methods have been investigated for the synthesis of such heterocycles, [13][14][15][16][17] but the most explored strategy involves cyclisation of an acylamidrazone intermediate. [18][19][20] Recently, the application of microwave (MW) irradiation in organic synthesis has been the focus of considerable attention and is becoming an increasingly popular technology, 21 owing to the rapid reaction rates, clean reaction conditions and ease of manipulation.…”

“…13 C NMR (100 MHz): d  151.0, 143.1, 134.0, 130.1, 130.0, 126.0, 10.8. 4-(4-Fluorobenzyl)-3-(4-nitrophenyl)-4H-1,2,4-triazole (3j): 1 H NMR (400 MHz): d  8.78 (1H, s), 8.31 (2H, d), 7.94 (2H, d), 7.16-7.10 (4H, m), 5.48 (2H, s).…”