62847-45-4

Upstream product

• 32990-21-9 Trifluoroacetonitrile oxide 
• 536-74-3 phenylacetylene 
• 44637-25-4 2,2,2-trifluoro-N-hydroxyacetimidoyl bromide 
• 135106-04-6 3-chloro-4,4,4-trifluoro-1-phenyl-2-buten-1-one 
• 326-06-7 1-Phenyl-4,4,4-trifluorobutane-1,3-dione 
• 58518-08-4 1,1,1-trifluoro-4-phenylbut-3-yn-2-one 
• 815-03-2 (trifluoroacetyl)hydroximoyl chloride 
• 753-90-2 trifluoroethylamine 
• 100-42-5 styrene 
• 354-64-3 Pentafluoroethyl iodide 
• 819-03-4 2,2,2-trifluoroacetaldehyde oxime 
• 93498-38-5 5-Phenyl-3-(trifluoromethyl)-4,5-dihydroisoxazole 

Downstream Products

• 75840-25-4 (Z)-3-amino-4,4,4-trifluoro-1-phenylbut-2-en-1-one 

Relevant academic research and scientific papers

A one-pot synthesis of 3-trifluoromethyl-2-isoxazolines from trifluoromethyl aldoxime

Functionalized 3-trifluoromethyl-2-isoxazolines and 3- trifluoromethylisoxazoles were easily prepared from trifluoromethyl aldoxime 2 under mild conditions by using DIB as oxidant. Theoretical studies of the reactivity of trifluoroacetonitrile oxide 4 toward olefins and alkynes were carried out. The 3-trifluoromethyl-2-isoxazolines were ring-opened with NaBH4 and NiCl2 to yield the corresponding trifluoromethylated ?-amino alcohols.

CYCLOADDITIONS OF TRIFLUOROACETONITRILE OXIDE WITH OLEFINS AND ACETYLENES.

The regio- and stereoselectivity of the cycloadditions of trifluoracetonitrile oxide (1) with olefins and acetylenes were described. The oxide 1, generated in situ from trifluoroacetohydroximoyl bromide etherate in the presence of triethylamine, reacted with various monosubstituted olefins and acetylenes to give exclusively 5-substituted 3-trifluoromethyl-2-isoxazolines and -isoxazoles, respectively, whereas 1 cyclized with 1,2-disubstituted olefins and acetylenes to result in the formation of a mixture of two regioisomeric products. On the other hand, the cycloaddition of 1 with (Z)- beta -methylstyrene afforded a mixture consisting of two regioisomeric isoxazolines retaining Z-configuration and one diastereoisomeric isoxazoline.

One-Pot Synthesis of Trifluoromethylated Iodoisoxazoles via the Reaction of Trifluoroacetohydroximoyl Chloride with Terminal Alkynes and N -Iodosuccinimide

Trifluoromethylated iodoisoxazoles have been synthesized by the reaction of trifluoroacetohydroximoyl chloride, alkynes, and N-iodosuccinimide in a one-pot reaction under metal-free and mild conditions. An array of iodoisoxazole compounds with a wide rang

Four-Component Reactions for the Synthesis of Perfluoroalkyl Isoxazoles

A four-component strategy for the synthesis of the isoxazole skeleton is developed. The approach achieves the synthesis of perfluoroalkyl isoxazoles by using simple perfluoroalkyl reagents. In addition, the unprecedented 3-azido-5-arylisoxazole formation

Cu-Catalyzed Synthesis of Fluoroalkylated Isoxazoles from Commercially Available Amines and Alkynes

A one-pot protocol for the construction of fluoroalkylated isoxazoles directly from commercially available amines and alkynes is described. The reaction is scalable, operationally simple, regioselective, mild, and tolerant of a broad range of functional groups. As such, it could be viewed as a click synthesis of fluoroalkylated isoxazoles. Preliminary mechanistic investigations reveal that the transformation involves an unprecedented Cu-catalyzed cascade sequence involving RfCHN2.

Synthesis of trifluoromethylated isoxazoles and their elaboration through inter- and intra-molecular C-H arylation

We report conditions for the preparation of a range of trifluoromethylated isoxazole building blocks through the cycloaddition reaction of trifluoromethyl nitrile oxide. It was found that controlling the rate (and therefore concentration) of the formation of the trifluoromethyl nitrile oxide was Critical for the preferential formation of the desired isoxazole products versus the furoxan dimer. Different conditions were optimised for both aryl- and alkyl-substituted alkynes. In addition, the reactivity at the isoxazole 4-position has been briefly explored for these building blocks. Conditions for intermolecular C-H arylation, lithiation and electrophile quench, and alkoxylation were all identified with brief substrate scoping that signifies useful tolerance to a range of functionalities. Finally, complementary processes for structural diversification through either intramolecular cyclisation or intermolecular cross-coupling were developed.

Synthesis of 3-phenyl-5-(trifluoromethyl)isoxazole and 5-phenyl-3- (trifluoromethyl)isoxazole

Reaction of 4,4,4-trifluoro-1-phenyl-1,3-butanedione with hydroxylamine led to the formation of 5-hydroxy-3-phenyl-5-(trifluoromethyl)-4,5-dihydroisoxazole which was dehydrated to 3-phenyl-5-(trifluoromethyl)isoxazole. This isomer can also be synthesized

Synthesis of fluorinated heterocycles

Selected 1,3-diketones having a trifluoromethyl group and/or a fluorine in the 2-position were condensed with aromatic hydrazines, hydroxylamine, urea, thiourea, guanidine, and substituted anilines producing pyrazoles, isoxazoles, pyrimidines, and quinolines, respectively, in yields ranging from 27 to 87%.

Synthesis of isomeric trifluoromethyl pyrazoles and isoxazoles

Three regioisomeric trifluoromethyl pyrazoles and four regioisomeric trifluoromethyl isoxazoles were completely selectively synthesized from three trifluoromethyl enones or acroleins (1, 2 and 3) and phenylhydrazine, azide or hydroxylamine.

FEATURES OF THE (2+3)-CYCLOADDITION OF TRIFLUOROACETONITRILE OXIDE

The (2+3)-cycloaddition of trifluoroacetonitrile oxide is a function of the donor and steric properties of dipolarophiles and usually proceeds regiospecifically.A significant temperature effect was found for the cycloaddition of trifluoroacetonitrile oxid