15765-00-1Relevant articles and documents
Organocatalytic Selective [3 + 2] Cycloadditions: Synthesis of Functionalized 5-Arylthiomethyl-1,2,3-triazoles and 4-Arylthio-1,2,3-triazoles
Reddy, G. Surendra,Reddy, L. Mallikarjuna,Kumar, A. Suresh,Ramachary, Dhevalapally B.
, p. 15488 - 15501 (2020)
An organocatalytic azide-ketone [3 + 2] cycloaddition (OrgAKC) of a variety of 1-aryl-3-(arylthio)propan-2-ones and 1-alkyl-3-(arylthio)propan-2-ones with different aryl/vinyl/alkyl azides is reported under ambient conditions to furnish the medicinally important 1,4-disubstituted-5-arylthiomethyl-1,2,3-triazoles and 1,5-disubstituted-4-arylthio-1,2,3-triazoles, respectively, in a regioselective manner with high yields/rates. With controlled and online NMR experiments, we proved that the reaction path is following the organocatalytic enolization through selective deprotonation followed by a [1,3]-H shift. Surprisingly, the [3 + 2] cycloaddition of aryl/vinyl/alkyl azides with the in situ-generated equilibrated thermodynamic ? kinetic enolates furnished the highly regioselective functionally rich 1,2,3-triazoles by discriminating their reactivities. This is the first report on the investigation of a selective OrgAKC with the regiomers of enolates generated in situ from the unsymmetrical carbonyl compounds. The reaction sustainability is explained with a few controlled experiments, mechanistic studies, and applications.
A general method of Suzuki-Miyaura cross-coupling of 4- and 5-halo-1,2,3-triazoles in water
Gribanov, Pavel S.,Chesnokov, Gleb A.,Topchiy, Maxim A.,Asachenko, Andrey F.,Nechaev, Mikhail S.
supporting information, p. 9575 - 9578 (2017/11/30)
A general method of the synthesis of 1,4,5-trisubstituted-1,2,3-triazoles by Suzuki-Miyaura cross-coupling from 4- and 5-halo-1,2,3-triazoles is reported. The reaction is mediated by an expanded-ring N-heterocyclic carbene palladium complex in water. The
Copper-mediated synthesis of 1,2,3-triazoles from N-tosylhydrazones and anilines
Chen, Zhengkai,Yan, Qiangqiang,Liu, Zhanxiang,Xu, Yiming,Zhang, Yuhong
supporting information, p. 13324 - 13328 (2014/01/06)
NNNifty targets: In a straightforward copper-mediated synthesis of 1,4-disubstituted and 1,4,5-trisubstituted 1,2,3-triazoles, readily available aniline and N-tosylhydrazone substrates underwent cyclization through Ci£N and Ni£N bond formation (see scheme