BIOMAT Database Logo BIOMAT Database Logo

Base-Promoted (3 + 2) Cycloaddition of Trifluoroacetohydrazonoyl Chlorides with Imidates En Route to Trifluoromethyl-1,2,4-Triazoles. 2022

Yue Zhang, and Jun-Liang Zeng, and Zhen Chen, and Ren Wang
Jiangsu Key Laboratory for the Research and Utilization of Plant Resources, the Jiangsu Provincial Platform for Conservation and Utilization of Agricultural Germplasm, Institute of Botany, Jiangsu Province and Chinese Academy of Sciences, Nanjing 210014, China.

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.

UI MeSH Term Description Entries
D007096 Imidoesters Esters of the hypothetical imidic acids. They react with amines or amino acids to form amidines and are therefore used to modify protein structures and as cross-linking agents. Imidates
D002712 Chlorides Inorganic compounds derived from hydrochloric acid that contain the Cl- ion. Chloride,Chloride Ion Level,Ion Level, Chloride,Level, Chloride Ion
D014230 Triazoles Heterocyclic compounds containing a five-membered ring with two carbon atoms and three nitrogen atoms with the molecular formula C2H3N3. Triazole
D061565 Cycloaddition Reaction Synthetic organic reactions that use reactions between unsaturated molecules to form cyclical products. Cycloaddition,Cycloaddition Reaction Techniques,Diels-Alder Reaction,Cycloaddition Reaction Technique,Cycloaddition Reactions,Diels Alder Reaction,Reaction Technique, Cycloaddition,Reaction Techniques, Cycloaddition,Reaction, Cycloaddition,Reaction, Diels-Alder,Reactions, Cycloaddition,Technique, Cycloaddition Reaction,Techniques, Cycloaddition Reaction

Related Publications

Yue Zhang, and Jun-Liang Zeng, and Zhen Chen, and Ren Wang
Synthesis of fused 3-trifluoromethyl-1,2,4-triazoles via base-promoted [3 + 2] cycloaddition of nitrile imines and 1H-benzo[d]imidazole-2-thiols.
September 2023, Organic & biomolecular chemistry,
Yue Zhang, and Jun-Liang Zeng, and Zhen Chen, and Ren Wang
Regioselective Synthesis of 5-Trifluoromethyl 1,2,4-Triazoles via [3 + 2]-Cycloaddition of Nitrile Imines with CF3CN.
October 2022, Molecules (Basel, Switzerland),
Yue Zhang, and Jun-Liang Zeng, and Zhen Chen, and Ren Wang
Radical-based route to 2-(trifluoromethyl)-1,3,4-oxadiazoles and trifluoromethyl-substituted polycyclic 1,2,4-triazoles and dihydrofurans.
March 2015, Organic letters,
Yue Zhang, and Jun-Liang Zeng, and Zhen Chen, and Ren Wang
En Route to 2-(Cyclobuten-1-yl)-3-(trifluoromethyl)-1H-indole.
February 2018, The Journal of organic chemistry,
Yue Zhang, and Jun-Liang Zeng, and Zhen Chen, and Ren Wang
Trifluoroacetic Anhydride Promoted Copper(I)-Catalyzed Interrupted Click Reaction: From 1,2,3-Triazoles to 3-Trifluoromethyl-Substituted 1,2,4-Triazinones.
August 2017, Angewandte Chemie (International ed. in English),
Yue Zhang, and Jun-Liang Zeng, and Zhen Chen, and Ren Wang
Synthesis of 3-Trifluoromethyl-1,2,4-triazolines and 1,2,4-Triazoles via Tandem Addition/Cyclization of Trifluoromethyl N-Acylhydrazones with Cyanamide.
May 2022, The Journal of organic chemistry,
Yue Zhang, and Jun-Liang Zeng, and Zhen Chen, and Ren Wang
Regioselective synthesis of 3-trifluoromethyl 1,2,4-triazoles via photocycloaddition of sydnone with CF3CN.
November 2022, Chemical communications (Cambridge, England),
Yue Zhang, and Jun-Liang Zeng, and Zhen Chen, and Ren Wang
Organophotoredox-mediated Formal [3+2]-Cycloaddition of 2H-Azirines with Aryldiazonium Salts: Direct Access to Trisubstituted 1,2,4-Triazoles.
April 2023, Chemistry, an Asian journal,
Yue Zhang, and Jun-Liang Zeng, and Zhen Chen, and Ren Wang
AgSbF6-promoted cycloaddition reaction of 2-trifluoromethyl-N-tosylaziridine with aldehydes.
December 2011, Organic letters,
Yue Zhang, and Jun-Liang Zeng, and Zhen Chen, and Ren Wang
Silver-Mediated [3 + 2] Cycloaddition of Azomethine Ylides with Trifluoroacetimidoyl Chlorides for the Synthesis of 5-(Trifluoromethyl)imidazoles.
March 2021, The Journal of organic chemistry,
Copied contents to your clipboard!