Access to (<i>Z</i>)-β-Substituted Enamides from <i>N</i>1-H-1,2,3-Triazoles
Tao Wang, Zongyuan Tang, Han Luo, Yi Tian, Mingchuan Xu, Qixing Lu, Baosheng Li
Abstract
A direct ring-opening/nucleophilic substitution reaction of N1-H-1,2,3-triazoles has been described. Divergent (Z)-β-halogen- or sulfonyl-substituted enamides could be stereospecifically synthesized in a tunable manner. This strategy might not only enable a new ring-opening method of N1-H-1,2,3-triazoles under nonmetal catalysis and mild reaction conditions but also offer a good opportunity to reliably access versatile (Z)-β-substituted enamides that could be used as synthetic precursors for further synthetic transformations.
Topics & Concepts
ChemistryRing (chemistry)HalogenCombinatorial chemistryNucleophileCatalysisNucleophilic substitutionReaction conditionsNonmetalStereochemistryMedicinal chemistryOrganic chemistryMetalAlkylCyclopropane Reaction MechanismsSynthesis and Catalytic ReactionsClick Chemistry and Applications