Synthesis of N-CF3 Amidines/Imidates/Thioimidates via N-CF3 Nitrilium Ions

Zhang, Ru Zhong; Huang, Wanqiao; Xu, Cong; Wang, Mang

doi:10.1021/acs.orglett.2c00647

Cited by 19 publications

(15 citation statements)

References 60 publications

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“…Very recently, related N -CF 3 amidines, imidates and thioimidates were prepared by the reaction of PhI(CF 3 )Cl with nitriles, followed by the addition of nucleophiles to the intermediate N -CF 3 nitriliums. 33…”

Section: Resultsmentioning

confidence: 99%

“…32 Another synthon, the N-CF 3 nitrilium ion, was introduced by Xu and Wang for the synthesis of N-CF 3 azoles and imido derivatives. 33,34 Despite the great progress in recent years, most of the strategies for this are limited to N-CF 3 compounds and methods for the synthesis of a wide range of N-fluoroalkyl compounds remain underdeveloped.…”

Section: Introductionmentioning

confidence: 99%

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Aza-Wolff rearrangement ofN-fluoroalkyl triazoles to ketenimines

Kubíčková,

Markos,

Voltrová

et al. 2023

Org. Chem. Front.

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Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Aza-Wolff rearrangement ofN-fluoroalkyl triazoles to ketenimines

Kubíčková,

Markos,

Voltrová

et al. 2023

Org. Chem. Front.

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“…As a continuation of their work, the authors exploited their N ‐CF 3 nitrilium ions to build N ‐CF 3 imine derivatives 47 by capturing amines, alcohols, and thiols, respectively (Scheme 44). [22] The amination of the N ‐CF 3 nitrilium has been realized with different N ‐heterocycles such as pyrazoles, imidazoles, indazoles, purine, triazole, and indoles, with primary and secondary amines. A wide range of N ‐CF 3 methanimine compounds 47 are isolated in good to excellent yields.…”

Section: N‐cf3 Via Nitrilium Cf3 From Phicf3clmentioning

confidence: 99%

Recent Advances in the Syntheses of N‐CF₃ Scaffolds up to Their Valorization

Crousse

2023

The Chemical Record

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This review provides a recent overview of the different synthetic routes of the N‐CF3 group. This scaffold can be prepared from the desulfurization of thiocabamoyl fluorides or isothiocyanates with fluoride ions. Electrophilic and radical trifluoromethylations are also a great way to generate this motif. This report also focuses on the valorization of some N‐CF3 compounds, which leads to new unknown N‐trifluoromethyl derivatives. Finally, the first metabolic stability studies will be given for certain structures.

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“…Furthermore, estrone analogue 54 could be generated in two steps in a total of 74% yield. Subsequently, the authors’ group developed the reaction of the N -CF 3 nitrilium ions 51 with N-, O-, and S-nucleophiles, resulting in various N -CF 3 amidines, imidates, and Thioimidates [ 81 ]. Very recently, they utilized hypervalent iodine reagent for the trifluoromethylation of 4-alkylamino-pyridine to generate N -CF 3 pyridinium salt which could be further translated to 2-functionlized nicotinaldehydes [ 82 ].…”

Section: Five-membered Heterocyclesmentioning

confidence: 99%

A Brief Review on the Synthesis of the N-CF3 Motif in Heterocycles

et al. 2023

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The trifluoromethyl group is widely recognized for its significant role in the fields of medicinal chemistry and material science due to its unique electronic and steric properties that can alter various physiochemical properties of the parent molecule, such as lipophilicity, acidity, and hydrogen bonding capabilities. Compared to the well-established C-trifluoromethylation, N-trifluoromethylation has received lesser attention. Considering the extensive contribution of nitrogen to drug molecules, it is predicted that constructing N-trifluoromethyl (N-CF3) motifs will be of great significance in pharmaceutical and agrochemical industries. This review is mainly concerned with the synthesis of heterocycles containing this motif. In three-membered heterocycles containing the N-CF3 motif, the existing literature mostly demonstrated the synthetic strategy, as it does for four- and larger-membered heterocycles. Certain structures, such as oxaziridines, could serve as an oxidant or building blocks in organic synthesis. In five-membered heterocycles, it has been reported that N-CF3 azoles showed a higher lipophilicity and a latent increased metabolic stability and Caco-2-permeability compared with their N-CH3 counterparts, illustrating the potential of the N-CF3 motif. Various N-CF3 analogues of drugs or bioactive molecules, such as sildenafil analogue, have been obtained. In general, the N-CF3 motif is developing and has great potential in bioactive molecules or materials. Give the recent development in this motif, it is foreseeable that its synthesis methods and applications will become more and more extensive. In this paper, we present an overview of the synthesis of N-CF3 heterocycles, categorized on the basis of the number of rings (three-, four-, five-, six- and larger-membered heterocycles), and focus on the five-membered heterocycles containing the N-CF3 group.

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Synthesis of N-CF₃ Amidines/Imidates/Thioimidates via N-CF₃ Nitrilium Ions

Cited by 19 publications

References 60 publications

Aza-Wolff rearrangement ofN-fluoroalkyl triazoles to ketenimines

Aza-Wolff rearrangement ofN-fluoroalkyl triazoles to ketenimines

Recent Advances in the Syntheses of N‐CF₃ Scaffolds up to Their Valorization

A Brief Review on the Synthesis of the N-CF3 Motif in Heterocycles

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Synthesis of N-CF3 Amidines/Imidates/Thioimidates via N-CF3 Nitrilium Ions

Cited by 19 publications

References 60 publications

Aza-Wolff rearrangement ofN-fluoroalkyl triazoles to ketenimines

Aza-Wolff rearrangement ofN-fluoroalkyl triazoles to ketenimines

Recent Advances in the Syntheses of N‐CF3 Scaffolds up to Their Valorization

A Brief Review on the Synthesis of the N-CF3 Motif in Heterocycles

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Product

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Synthesis of N-CF₃ Amidines/Imidates/Thioimidates via N-CF₃ Nitrilium Ions

Recent Advances in the Syntheses of N‐CF₃ Scaffolds up to Their Valorization