Deprotometalation-iodolysis and computed CH acidity of 1,2,3- and 1,2,4-triazoles. Application to the synthesis of resveratrol analogues.

摘要: 1-Aryl- and 2-aryl-1,2,3-triazoles were synthesized by N-arylation of the corresponding azoles using aryl iodides. The deprotometalations 1-phenyl-1,2,3-triazole -1,2,4-triazole performed a 2,2,6,6-tetramethylpiperidino-based mixed lithium-zinc combination occurred at most acidic site, affording iodolysis 5-substituted derivatives. Dideprotonation was noted from 1-(2-thienyl)-1,2,4-triazole increasing amount base. From 2-phenyl-1,2,3-triazoles, in particular 2-(4-trifluoromethoxy)phenyl-1,2,3-triazole, reactions 4 position triazolyl, but also ortho to triazolyl on phenyl group, observed. results analyzed with help CH acidities substrates, determined THF solution DFT B3LYP method. 4-Iodo-2-phenyl-1,2,3-triazole 4-iodo-2-(2-iodophenyl)-1,2,3-triazole next involved Suzuki coupling furnish 4-arylated 4,2’-diarylated When evaluated for biological activities, latter (which are resveratrol analogues) showed moderate antibacterial activity promising antiproliferative effect against MDA-MB-231 cell line.