Synthesis of Multisubstituted 1,2,3-Triazoles: Regioselective Formation and Reaction Mechanism
Tzu-Ching Chi, Po‐Chun Yang, Shao-Kang Hung, Hui‐Wen Wu, Hong-Chi Wang, Hsin‐Kuan Liu, Liwen Liu, Ho‐Hsuan Chou
Abstract
A synthetically useful approach to functionalized triazoles is described via the reaction of β-carbonyl phosphonates and azides. 1,4- and 1,5-disubstituted and 1,4,5-trisubstituted triazoles can be regio- and chemoselectively accessed under mild conditions in good to excellent yields (31 examples, up to 99%). A mechanism is proposed that rationalizes the avoidance of the 4-phosphonate byproducts, which is aligned with crystallographic and experimental evidence.
Topics & Concepts
ChemistryRegioselectivityPhosphonateCombinatorial chemistryMechanism (biology)Reaction mechanismReaction conditionsComputational chemistryStereochemistryOrganic chemistryCatalysisEpistemologyPhilosophyClick Chemistry and ApplicationsChemical Synthesis and AnalysisHIV/AIDS drug development and treatment