Azirine-triazole hybrids: selective synthesis of 5-(2H-azirin-2-yl)-, 5-(1H-pyrrol-2-yl)-1H-1,2,3-triazoles and 2-(5-(2H-azirin-2-yl)-1H-1,2,3-triazol-1-yl)pyridines

Abstract

Azirine-triazole hybrids, 1-R-5-(3-aryl-2H-azirin-2-yl)-1H-1,2,3-triazoles, were selectively synthesized by reaction of 1-(3-aryl-2H-azirin-2-yl)-2-(triphenylphosphoranylidene)ethanones with tosyl and (E)-2-benzoylvinyl azides in high yields at rt. The reaction with 2-azidopyridine makes it possible to obtain azirine-triazole-pyridine...

Acridine–Isoxazole and Acridine–Azirine Hybrids: Synthesis, Photochemical Transformations in the UV/Visible Radiation Boundary Region, and Anticancer Activity

“…Scheme 5. Relative Gibbs free energies for the transformations of pyrenyl-and dinyl-substituted nitrile ylides (in kcal/mol, 298 K, DFT B3LYP-D3/6-311+G(d,p) level with model for MeCN) [43]. Scheme 5.…”

“…Azirine 32, linked to acridine by a triazole bridge, was also synthesized by the reaction of 1-(3-phenyl-2H-azirin-2-yl)-2-(triphenylphosphoranylidene)ethanone 30 with 9-azidoacridine 31, according to the procedure developed in the work [43], at a 77% yield (Scheme 7). However, the photolysis of azirine 32 in acetonitrile, in the presence of DMAD or PMI (20 equiv.)…”

2H‐Azirines: Recent Progress in Synthesis and Applications

“…Compared by the reaction with TsN 3 , the reaction with TfN 3 yields α‐diazo ketones instead of azirine‐triazole hybrids (Scheme 23). [39] The decomposition of the starting materials or products have blocked the reaction with BnN 3 in refluxing toluene. DFT calculations suggested that the reactions of α‐carbonylphosphoranes with both sulfonyl azides and alkyl azides proceed via a non‐concerted mechanism, involving the attack of the terminal azide nitrogen on the phosphorane nucleophilic C1 to form the intermediate zwitterion and its cyclization and elimination of triphenylphosphine oxide to 1,5‐disubstituted triazoles.…”