CuI-mediated benzannulation of (<i>ortho</i>-arylethynyl)phenylenaminones to assemble α-aminonaphthalene derivatives

Jiang, Wen-Nian; Zhao, Qinglan; Cheng, Wen-Shuo; Xiao, Jun‐An; Xiang, Hao-Yue; Chen, Kai; Ye, Hua

doi:10.1039/d1qo00298h

Cited by 8 publications

(1 citation statement)

References 31 publications

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“…Owing to the internal highest occupied molecular orbital heightening effect, enaminones have been disclosed to possess excellent application in the designation of transition-metal-free and sustainable synthetic reactions . Particularly, employing enaminones as building blocks has been identified with highly broad application in the construction of aromatic cycles, including both heteroaryls and carboaryls . In this context, we hypothesized that it is possible to develop a more convenient and atom-economical method for the synthesis cinnolines by employing enaminone as the main building block without using transition-metal catalysts .…”

Section: Introductionmentioning

confidence: 99%

Catalyst-Free Cascade Annulation of Enaminones and Aryl Diazonium Tetrafluoroboronates for Cinnoline Synthesis and the Anti-Inflammatory Activity Study

et al. 2023

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A simple and concise method for the synthesis of cinnolines has been developed by the reactions of readily available enaminones and aryl diazonium tetrafluoroboronates. The reactions run efficiently to provide cinnolines with broad diversity in the substructure by heating in dimethyl sulfoxide without using any catalyst or additive. In addition, the primary investigation of the anti-inflammatory activity of these products leads to the observation of p-chlorobenzoyl (3f) and p-nitrobenzoyl (3j) cinnolines as attractive anti-inflammatory compounds in vitro.

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Section: Introductionmentioning

confidence: 99%

Catalyst-Free Cascade Annulation of Enaminones and Aryl Diazonium Tetrafluoroboronates for Cinnoline Synthesis and the Anti-Inflammatory Activity Study

et al. 2023

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Recent Advances in Reactions Using Enaminone in Water or Aqueous Medium

et al. 2022

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Enaminones have in the past decade received renewed interest in organic synthesis by acting as highly versatile building blocks. Particularly, the featured amino and carbonyl group in the enaminone structure endow them with the ability of tolerating water via hydrogen bonding effect. Thus, designing synthetic methods in aqueous medium with enaminones as the main building blocks has received extensive attention and notable success. Based on our longstanding efforts and interests in enaminone chemistry, we review herein the research advances in enaminone participated organic synthesis in aqueous medium.

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Brønsted Acid‐Promoted Benzannulation of o‐Alkynylbenzaldehyde and Alkyne, and the Positive Effect of Propargyl Alcohol

et al. 2022

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Bromotrimethylsilane-promoted benzannulation of o-alkynylbenzaldehydes and alkynes to yield 1naphthyl aryl ketones is reported. The reaction conditions are mild, metal-free, and do not require pretreatment/protection of the substrates. We found that aryl propargyl alcohols were very effective substrates for this reaction, compared with other alkynes. Studies on the reaction scope, monitoring the reaction progress by 1 H NMR, and theoretical calculations suggest that isochromenylium (benzopyrilium) ion is the key reaction intermediate.

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CuI-mediated benzannulation of (ortho-arylethynyl)phenylenaminones to assemble α-aminonaphthalene derivatives

Abstract: A copper-mediated annulation protocol of new (ortho-arylethynyl)phenyl enaminones bearing a N,N-dimethylamine moiety was developed to facilely install a series of α-aminonaphthalene derivatives. Simple manuipulation of exogenous amine readily offers the...

Cited by 8 publications

References 31 publications

Catalyst-Free Cascade Annulation of Enaminones and Aryl Diazonium Tetrafluoroboronates for Cinnoline Synthesis and the Anti-Inflammatory Activity Study

Catalyst-Free Cascade Annulation of Enaminones and Aryl Diazonium Tetrafluoroboronates for Cinnoline Synthesis and the Anti-Inflammatory Activity Study

Recent Advances in Reactions Using Enaminone in Water or Aqueous Medium

Brønsted Acid‐Promoted Benzannulation of o‐Alkynylbenzaldehyde and Alkyne, and the Positive Effect of Propargyl Alcohol

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