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Base-Promoted (3 + 2) Cycloaddition of Trifluoroacetohydrazonoyl Chlorides with Imidates En Route to Trifluoromethyl-1,2,4-Triazoles

Yue Zhang, Jun‐Liang Zeng, Zhen Chen, Ren Wang

2022The Journal of Organic Chemistry33 citationsDOI

Abstract

A base-mediated (3 + 2) cycloaddition of trifluoroacetohydrazonoyl chlorides with imidates for the construction of 3-trifluoromethyl-1,2,4-triazoles has been described. This reaction is characterized by readily starting materials, simple reaction conditions, good yields, a broad substrate scope, and excellent regioselectivity. The utility of this protocol has been validated by the synthesis of a drug-like molecule.

Topics & Concepts

CycloadditionRegioselectivityTrifluoromethylChemistrySubstrate (aquarium)Base (topology)Scope (computer science)Combinatorial chemistryMoleculeOrganic chemistryMedicinal chemistryComputer scienceCatalysisMathematicsProgramming languageAlkylMathematical analysisGeologyOceanographyFluorine in Organic ChemistrySynthesis and Reactions of Organic CompoundsClick Chemistry and Applications
Base-Promoted (3 + 2) Cycloaddition of Trifluoroacetohydrazonoyl Chlorides with Imidates En Route to Trifluoromethyl-1,2,4-Triazoles | Litcius