70314-81-7Relevant academic research and scientific papers
Silver-Mediated [3 + 2] Cycloaddition of Azomethine Ylides with Trifluoroacetimidoyl Chlorides for the Synthesis of 5-(Trifluoromethyl)imidazoles
Yang, Hefei,Lu, Shu-Ning,Chen, Zhengkai,Wu, Xiao-Feng
supporting information, p. 4361 - 4370 (2021/03/09)
A silver-mediated [3 + 2] cycloaddition of azomethine ylides with trifluoroacetimidoyl chlorides for the rapid assembly of 5-(trifluoromethyl)imidazoles has been developed. Notable features of the reaction include readily accessible reagents, a broad substrate scope, and high efficiency. The protocol can be successfully applied to construct the analogue of the specific allosteric modulator of GABAA receptors. The silver species could be recycled by a simple operation.
Synthesis of 5-Trifluoromethyl-1,2,4-Triazoles via Metal-Free Annulation of Trifluoroacetimidohydrazides and Methyl Ketones
Chen, Zhengkai,Tang, Jianhua,Wu, Xiao-Feng,Zhang, Jiajun
, p. 3060 - 3069 (2021/05/10)
A metal-free approach for the synthesis of 5-trifluoromethyl-1,2,4-triazoles via I2-mediated [4+1] annulation of readily available trifluoroacetimidohydrazides and methyl ketones has been achieved. The transformation involves iodination/Kornblum oxidation, intermolecular dehydration condensation and an iodine-mediated intramolecular cyclization/aromatization sequence. The developed protocol can be easily scaled up to 3 mmol scale without obvious efficiency decrease and be implemented by a consecutive one-pot manner. (Figure presented.).
The cascade coupling/iodoaminocyclization reaction of trifluoroacetimidoyl chlorides and allylamines: metal-free access to 2-trifluoromethyl-imidazolines
Chen, Zhengkai,Du, Shiying,Song, Yufei,Wang, Le-Cheng,Wu, Xiao-Feng
supporting information, p. 6115 - 6119 (2021/07/21)
A metal-free cascade coupling/iodoaminocyclization reaction for the rapid assembly of 2-trifluoromethyl-imidazolines has been disclosed. The transformation applies readily accessible trifluoroacetimidoyl chlorides, allylamines andN-iodosuccinimides as the starting substrates, achieving an efficient and straightforward pathway to construct diverse imidazoline derivatives. Excellent efficiency of the reaction is observed (higher than 90% isolated yield for half of the examples), and the obtained imidazoline products bearing a pendent iodomethyl group could be easily transformed into other synthetically valuable compounds.
Annulation of CF3-Imidoyl Sulfoxonium Ylides with 1,3-Dicarbonyl Compounds: Access to 1,2,3-Trisubstituted 5-Trifluoromethylpyrroles
Wen, Si,Tian, Qingyu,Chen, Yanhui,Zhang, Yuqing,Cheng, Guolin
supporting information, p. 7407 - 7411 (2021/10/12)
A lithium-bromide-promoted nucleophilic substitution/annulation cascade reaction between CF3-imidoyl sulfoxonium ylides and 1,3-dicarbonyl compounds has been established, and the corresponding 1,2,3-trisubstituted 5-trifluoromethylpyrroles have been obtai
Elemental Sulfur and Dimethyl Sulfoxide-Promoted Oxidative Cyclization of Trifluoroacetimidohydrazides with Methylhetarenes for the Synthesis of 3-Hetaryl-5-trifluoromethyl-1,2,4-triazoles
Chen, Zhengkai,Tang, Jianhua,Wu, Xiao-Feng,Zhang, Jiajun
supporting information, p. 3443 - 3447 (2021/11/10)
A metal-free approach for the synthesis of 3-hetaryl-5-trifluoromethyl-1,2,4-triazoles via sulfur/dimethyl sulfoxide-promoted oxidative cyclization of readily available trifluoroacetimidohydrazides with methylhetarenes has been developed. This transformation proceeds in cascade sulfur-mediated generation of thioaldehyde, condensation, intramolecular cyclization and oxidative aromatization sequence.
Palladium-Catalyzed Four-Component Carbonylative Cyclization Reaction of Trifluoroacetimidoyl Chlorides, Propargyl Amines, and Diaryliodonium Salts: Access to Trifluoromethyl-Containing Trisubstituted Imidazoles
Chen, Zhengkai,Wang, Wei-Feng,Yang, Hefei,Wu, Xiao-Feng
supporting information, p. 1980 - 1984 (2020/03/04)
A palladium-catalyzed four-component carbonylative cyclization reaction for the expeditious construction of trifluoromethyl-containing trisubstituted imidazoles has been achieved. With readily accessible trifluoroacetimidoyl chlorides, propargyl amines, a
FeCl3-Mediated Synthesis of 2-(Trifluoromethyl)quinazolin-4(3 H)-ones from Isatins and Trifluoroacetimidoyl Chlorides
Wang, Le-Cheng,Du, Shiying,Chen, Zhengkai,Wu, Xiao-Feng
supporting information, p. 5567 - 5571 (2020/07/14)
An FeCl3-mediated cascade coupling/decarbonylative annulation reaction for the efficient construction of 2-(trifluoromethyl)quinazolin-4(3H)-ones has been developed. This transformation employs readily available isatins and trifluoroacetimidoyl chlorides as the starting materials, providing a facile and practical route to diverse biologically relevant quinazolin-4(3H)-one derivatives. A plausible reaction pathway has been proposed based on the mechanistic observations.
A Convenient FeCl3-Mediated Synthesis of 5-Trifluoromethyl-1,2,4-triazoles from Trifluoroacetimidoyl Chlorides and Hydrazides
Du, Shiying,Wang, Le-Cheng,Yang, Zuguang,Chen, Zhengkai,Wu, Xiao-Feng
supporting information, p. 5130 - 5134 (2020/10/06)
A low cost FeCl3-mediated cascade annulation of trifluoroacetimidoyl chlorides and hydrazides for the efficient synthesis of 5-trifluoromethyl-1,2,4-triazoles has been developed. The transformation proceeds through a cascade base-promoted intermolecular C?N bond formation and FeCl3-mediated intramolecular dehydration sequence under mild conditions. The protocol exhibits many notable features and can be readily scaled up to gram scale. (Figure presented.).
Expeditious Synthesis of 6-Fluoroalkyl-Phenanthridines via Palladium-Catalyzed Norbornene-Mediated Dehydrogenative Annulation
Wang, Zhuo,Li, Tongyu,Zhao, Jinghui,Shi, Xiaonan,Jiao, Dequan,Zheng, Han,Chen, Chen,Zhu, Bolin
supporting information, p. 6640 - 6645 (2018/10/25)
A novel palladium-catalyzed, norbornene-mediated intermolecular dehydrogenative annulation approach for the synthesis of 6-fluoroalkyl-phenanthridines from aryl iodides and fluorinated imidoyl chlorides, which are important structural motifs for bioactive molecules, is reported. Fluorinated imidoyl chlorides served as a new type of electrophilic reagent in the Catellani-type reaction, which, in turn, could be readily prepared from various anilines and fluorinated carboxylic acids. Control experiments were carried out to study the mechanism of the reaction. This transformation is scalable and tolerates a broad range of functional groups.
Cu-catalyzed tandem reactions of fluorinated alkynes with sulfonyl azides en route to 2-trifluoromethylquinolines
Li, Yajun,Zhang, Lisi,Zhang, Li,Wu, Yongming,Gong, Yuefa
supporting information, p. 7267 - 7270 (2013/10/22)
A novel method for the synthesis of 2-trifluoromethylquinolines via Cu-catalyzed tandem reactions was reported. A strong electronic effect was observed, but the steric effect was negligible.
