Chemoselective Reactions of Isocyanates with Secondary Amides: One-Pot Construction of 2,3-Dialkyl-Substituted Quinazolinones

Lin, Youxi; He, Shu-Fan; Geng, Hui; Xiao, Yuchen; Ji, Kan-Lei; Zheng, Jian‐Feng; Huang, Pei‐Qiang

doi:10.1021/acs.joc.0c02929

Cited by 10 publications

(6 citation statements)

References 77 publications

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“…Owing to the special feature of the -N=C=O functional group similar to heterocumulene, a series of carbon-based nucleophilic addition reactions have been achieved. [37][38][39][40][41][42][43][44][45][46] Above all, isocyanates have been seen as a significant synthetic building block of amides which could be attacked by radical species and display good reactivity. In 2015, Kanai et al synthesized a series of tertiary carbamates from isocyanates without prefunctionalization or installation of a directing group.…”

Section: Letter Synlettmentioning

confidence: 99%

Photoinduced Direct Carbamoylation of Ethers with Isocyanates towards the Synthesis of α-Amide-Substituted Ether Derivatives

Qi,

Li,

et al. 2024

Synlett

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Photoinduced carbamoylation of ethers using isocyanates as amide sources was accomplished under mild and environmentally friendly reaction conditions. A series of isocyanates were tolerated in this protocol to construct α-amide substituted ether derivatives with desired yields. The method featured broad substrate scope and good functional group tolerance, which could play an important role in the construction of biological molecules with ethers.

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Section: Letter Synlettmentioning

confidence: 99%

Photoinduced Direct Carbamoylation of Ethers with Isocyanates towards the Synthesis of α-Amide-Substituted Ether Derivatives

Qi,

Li,

et al. 2024

Synlett

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“…Distinctive methods involve utilizing the nitrogen of isocyanates as a nucleophile to react with nitrilium ions [164] (as shown in Figure 31d), as well as a photochemically induced radical addition to the isocyanate carbon [165] (depicted in Figure 31e). Both approaches are innovative and capitalize on the unique reactivity of isocyanates.…”

Section: Amides From Carbonyl‐containing Compoundsmentioning

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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“…Broad functional group tolerances, mild setup procedure, and good chemoselectivity are some of the salient features of this protocol. The synthetic application of the present protocol was established by the acid-catalyzed reaction of product 51d with 4-formylbenzonitrile to form the biologically active 2-styrylquinazolinones such as product 52 ( Scheme 13 ) ( Lin et al, 2021 ).…”

Section: Synthesis Of Quinazolinones From Two-component Organocatalyt...mentioning

confidence: 99%

Recent advances and prospects in the organocatalytic synthesis of quinazolinones

et al. 2022

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Quinazolinone, a bicyclic compound, comprises a pyrimidine ring fused at 4´ and 8´ positions with a benzene ring and constitutes a substantial class of nitrogen-containing heterocyclic compounds on account of their frequent existence in the key fragments of many natural alkaloids and pharmaceutically active components. Consequently, tremendous efforts have been subjected to the elegant construction of these compounds and have recently received immense interest in synthetic and medicinal chemistry. The domain of synthetic organic chemistry has grown significantly over the past few decades for the construction of highly functionalized therapeutically potential complex molecular structures with the aid of small organic molecules by replacing transition-metal catalysis. The rapid access to this heterocycle by means of organocatalytic strategy has provided new alternatives from the viewpoint of synthetic and green chemistry. In this review article, we have demonstrated a clear presentation of the recent organocatalytic synthesis of quinazolinones of potential therapeutic interests and covered the literature from 2015 to date. In addition to these, a clear presentation and understanding of the mechanistic aspects, features, and limitations of the developed reaction methodologies have been highlighted.

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Chemoselective Reactions of Isocyanates with Secondary Amides: One-Pot Construction of 2,3-Dialkyl-Substituted Quinazolinones

Cited by 10 publications

References 77 publications

Photoinduced Direct Carbamoylation of Ethers with Isocyanates towards the Synthesis of α-Amide-Substituted Ether Derivatives

Photoinduced Direct Carbamoylation of Ethers with Isocyanates towards the Synthesis of α-Amide-Substituted Ether Derivatives

Contemporary Approaches for Amide Bond Formation

Recent advances and prospects in the organocatalytic synthesis of quinazolinones

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