Palladium‐Catalyzed Carbonylative Synthesis of 2‐(Trifluoromethyl)quinazolin‐4(3<i>H</i>)‐ones from Trifluoroacetimidoyl Chlorides and Nitro Compounds

Wang, Le‐Cheng; Chen, Zhengkai; Wu, Xiao‐Feng

doi:10.1002/adsc.202001502

Cited by 26 publications

(10 citation statements)

References 53 publications

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“…[34] On the other hand, imidoyl halides (aza-analogs of acyl halides) are intermediates widely utilized in the synthesis of nitrogen-containing compounds. [35] Especially, trifluoroacetimidoyl halides have recently attracted research interest [36][37][38][39][40][41][42][43] due to the possibility of the introduction of the medicinally important trifluoromethyl group. [44] Trifluoroacetimidoyl chlorides are, among other reactions, used in the preparation of amides, imines or amidines, and in the synthesis of nitrogen-containing three-, five-, six-and seven-membered heterocycles.…”

Section: Introductionmentioning

confidence: 99%

Haloalkenyl Imidoyl Halides as Multifacial Substrates in the Stereoselective Synthesis of N‐Alkenyl Compounds

et al. 2021

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N‐Alkenyl compounds are versatile synthetic building blocks and their stereoselective transformations are key processes in the synthesis of many prominent classes of natural products, pharmaceuticals, and agrochemicals. However, a large structural variety of known N‐alkenyl compounds and their diverse reactivity have so far precluded the development of a general method for their stereoselective synthesis. Herein we present an aluminum halide‐mediated, highly stereoselective, efficient and scalable transformation of commercially available N‐fluoroalkyl‐1,2,3‐triazoles to N‐haloalkenyl imidoyl halides, and demonstrate their use in the synthesis of stereodefined N‐alkenyl amides, amidines, imines, hydrazonoamides, imidothioates, iminophosphonates, 1,2,4‐triazoles and tetrazoles. The reaction is of wide scope on both the triazole substrate and aluminum halide, providing highly functionalized products. Mechanistic and computational investigations suggest a reaction mechanism involving the triazole ring opening, initiated by the coordination of nitrogen one of the triazole ring to the Lewis acid, N2 elimination and the formation of a vinyl cation intermediate, which reacts with nitrogen‐bound aluminum halide, followed by a series of halide exchange reactions on C−X and Al−X bonds.

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Section: Introductionmentioning

confidence: 99%

Haloalkenyl Imidoyl Halides as Multifacial Substrates in the Stereoselective Synthesis of N‐Alkenyl Compounds

et al. 2021

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“…This strategy has also been extended to the preparation of oxindoles [204] and quinazolinones. [205] Additionally, Ma and coworkers [203] introduced a unique utilization of CO as the carbon source in a reductive protocol for nitro compound formylation (depicted in Figure 43).…”

Section: Carbonyl Insertionmentioning

confidence: 99%

Contemporary Approaches for Amide Bond Formation

Acosta‐Guzmán,

Ojeda‐Porras,

Gamba‐Sánchez

2023

Adv Synth Catal

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Amide bond construction has garnered significant interest in recent decades due to amides being one of the most prevalent functional groups among bioactive molecules. Out of the thirty‐seven new drugs approved by the FDA in 2022, eleven are small molecules containing at least one amide bond. Additionally, there are nineteen large molecules approved as new drugs, some of which have peptide structures, and therefore, also bear amide bonds. In recent years, multiple teams have embraced the challenge of developing more efficient methods for amide bond formation. This dedication has led to numerous publications appearing monthly in prestigious journals, showcasing significant advancements in this field. The primary goal of this review is to present the most viable strategies for constructing the amide bond. It is crucial to differentiate between amide bond formation and amide synthesis; hence, the focus is on describing specific methods for forming new C(O)−N bonds. In particular, this review concentrates on the methods developed within the last six years. There is a particular emphasis on new approaches that consider the thought process when selecting the starting materials and functional groups. This approach ensures coverage of all the most common chemical transformations that yield new amide bonds.

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“…Wu, Chen and co-workers disclosed a palladium-catalyzed multi-component carbonylative cyclization reaction of TFAICs and nitro compounds for the construction of 2-(trifluoromethyl)quinazolin-4(3 H )-ones in good to excellent yields (Scheme 20). 30 Mo(CO) 6 as a solid CO surrogate and a reducing reagent in the reaction. The reduction of nitro compounds by Mo(CO) 6 could produce amines through several possible intermediates, including nitrosobenzene, N -phenyl hydroxylamine, azobenzene and 1,2-diphenylhydrazine, which acted as reactive intermediates in the reaction.…”

Section: Synthesis Of Cf3-containing Heterocycles From Trifluoroaceti...mentioning

confidence: 99%

Construction of trifluoromethyl-containing heterocycles from trifluoroacetimidoyl chlorides and derivatives

et al. 2023

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Palladium‐Catalyzed Carbonylative Synthesis of 2‐(Trifluoromethyl)quinazolin‐4(3H)‐ones from Trifluoroacetimidoyl Chlorides and Nitro Compounds

Cited by 26 publications

References 53 publications

Haloalkenyl Imidoyl Halides as Multifacial Substrates in the Stereoselective Synthesis of N‐Alkenyl Compounds

Haloalkenyl Imidoyl Halides as Multifacial Substrates in the Stereoselective Synthesis of N‐Alkenyl Compounds

Contemporary Approaches for Amide Bond Formation

Construction of trifluoromethyl-containing heterocycles from trifluoroacetimidoyl chlorides and derivatives

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