A copper-catalyzed three component reaction of aryl acetylene, sulfonyl azide and enaminone to form iminolactone <i>via</i> 6π electrocyclization

Sun, Jiarui; Cheng, Xiangsheng; Mansaray, John Kamanda; Fei, Weihong; Wan, Jie‐Ping; Yao, Weijun

doi:10.1039/c8cc06868b

Cited by 23 publications

(9 citation statements)

References 66 publications

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“…(Scheme ). For CuAAC/ring cleavage reaction, CuI/R 3 N is the most efficient catalytic system. This strong basic condition limited the application of the reaction in dual catalyst systems, and certain substrates such as terminal ynones would undergo self-condensation under basic conditions .…”

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confidence: 99%

CuX Dual Catalysis: Construction of Oxazolo[2,3-b][1,3]oxazines via a Tandem CuAAC/Ring Cleavage/[4+2+3] Annulation Reaction

et al. 2022

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CuX as a simple dual catalyst strategy that promotes the tandem transformations of fused oxazolo[2,3-b][1,3]oxazines has been developed. Copper catalyzed terminal ynones, sulfonyl azides, and nitriles for the CuAAC/ring cleavage/[4+2] annulation reaction, while the halogen catalyzed ring cleavage and [2+3] annulation of oxiranes to form the final fused products. This study provides a four-component, one-pot strategy for synthesizing complex fused heterocycles from simple ingredients and expands the application of CuAAC in organic synthesis.

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confidence: 99%

CuX Dual Catalysis: Construction of Oxazolo[2,3-b][1,3]oxazines via a Tandem CuAAC/Ring Cleavage/[4+2+3] Annulation Reaction

et al. 2022

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“…In 2018, Yao and team established a three-component reaction to form iminolactone from aryl acetylene, enaminone and sulfonyl azide through 6π electrocyclization ( Scheme 26 ). 35 Synthesis proceeds via reaction of in situ generated metalated ketenimine from copper( i )-catalyzed alkyne–azide cycloaddition (CuAAC) with enaminone followed by 6π electrocyclization. Model substrates chosen was p -tolyl enaminone, phenylacetylene and p -toluenesulfonyl azide.…”

Section: Synthesis Of Heterocyclesmentioning

confidence: 99%

Recent developments and perspectives in the copper-catalyzed multicomponent synthesis of heterocycles

2021

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“…In 2018, Yao's group described copper-catalyzed tandem multicomponent reactions (MCRs) with a 6-electrocyclization as a pivotal step, in which the metalated ketenimine generated in situ from alkyne-azide cycloaddition (CuAAC) attacked the enaminone (Scheme 51). 54 Thus, various substituted iminolactones were obtained from a broad range of enaminones, aryl acetylenes and sulfonyl azides J. Huang, F. Yu…”

Section: Review Synthesismentioning

confidence: 99%

Recent Advances in Organic Synthesis Based on N,N-Dimethyl Enaminones

Huang

2020

Synthesis

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Enaminones are gaining increasing interest because of their unique properties and their importance in organic synthesis as versatile building blocks. N,N-Dimethyl enaminones offer a better leaving group (a dimethylamine group) than other enaminones, and allow further elaboration via a range of facile chemical transformations. Over the past five years, there have been an increasing number of reports describing the synthetic applications of N,N-dimethyl enaminones. This review provides a comprehensive overview on the synthetic applications of N,N-dimethyl enaminones that have been reported since 2016.1 Introduction2 Direct C(sp2)–H α-Functionalization2.1 Synthesis of α-Sulfenylated N,N-Dimethyl Enaminones2.2 Synthesis of α-Thiocyanated N,N-Dimethyl Enaminones2.3 Synthesis of α-Acyloxylated N,N-Dimethyl Enaminones3 Functionalization Reactions via C=C Double Bond Cleavage3.1 Synthesis of Functionalized Methyl Ketones3.2 Synthesis of α-Ketoamides, α-Ketoesters and 1,2-Diketones3.3 Synthesis of N-Sulfonyl Amidines4 Construction of All-Carbon Aromatic Scaffolds4.1 Synthesis of Benzaldehydes4.2 Synthesis of the Naphthalenes5 Construction of Heterocyclic Scaffolds5.1 Synthesis of Five-Membered Heterocycles5.2 Synthesis of Six-Membered Heterocycles5.3 Synthesis of Quinolines 5.4 Synthesis of Functionalized Chromones5.5 Synthesis of Other Fused Polycyclic Heterocycles6 Conclusions and Perspectives

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A copper-catalyzed three component reaction of aryl acetylene, sulfonyl azide and enaminone to form iminolactone via 6π electrocyclization

Abstract: We developed a copper-catalyzed three component reaction of aryl acetylene, enaminone and sulfonyl azide to construct iminolactone via copper-catalyzed alkyne–azide cycloaddition (CuAAC), Michael addition of metalated ketenimine followed by elimination and 6π electrocyclization.

Cited by 23 publications

References 66 publications

CuX Dual Catalysis: Construction of Oxazolo[2,3-b][1,3]oxazines via a Tandem CuAAC/Ring Cleavage/[4+2+3] Annulation Reaction

CuX Dual Catalysis: Construction of Oxazolo[2,3-b][1,3]oxazines via a Tandem CuAAC/Ring Cleavage/[4+2+3] Annulation Reaction

Recent developments and perspectives in the copper-catalyzed multicomponent synthesis of heterocycles

Recent Advances in Organic Synthesis Based on N,N-Dimethyl Enaminones

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