Palladium catalyzed tandem cyclization of acryloylbenzamides and <i>N</i>-arylacrylamides with epoxides: access to functionalized isoquinolinediones and oxindoles

Lu, Xiao-Yu; Shui, Fu-Yi; Zhang, Xiang; Huang, Rui; Wang, Zi-Zhen; Song, Yi-Wei; Jiang, Fan; Yang, Gui-Xian; Sun, Yan-Xi

doi:10.1039/d3qo01243c

Org. Chem. Front.

2023

DOI: 10.1039/d3qo01243c

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Palladium catalyzed tandem cyclization of acryloylbenzamides and N-arylacrylamides with epoxides: access to functionalized isoquinolinediones and oxindoles

Xiao-Yu Lu,

Fu-Yi Shui,

Xiang Zhang

et al.

Abstract: Herein, a practical and efficient tandem cyclization ring-opening coupling of acryloylbenzamides and N-arylacrylamides with epoxides is reported.

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Cited by 5 publications

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Recent advances in constructing efficient materials for electrocatalytic oxidation of propylene

Zhao,

Liu,

et al. 2025

Journal of Molecular Structure

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Recent advances in constructing efficient materials for electrocatalytic oxidation of propylene

Zhao,

Liu,

et al. 2025

Journal of Molecular Structure

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Photocatalytic Proton-Coupled Electron Transfer Enabled Radical Cyclization for Isoquinoline-1,3-diones Synthesis

Zhang,

Song,

Sun

et al. 2024

J. Org. Chem.

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Radical cyclization has been demonstrated to be an efficient method to access functionalized heterocycles from easily accessible raw materials. Described herein is the development of a photocatalytic proton-coupled electron transfer (PCET) strategy for the synthesis of isoquinoline-1,3-diones using readily prepared naphthalimide (NI)-based organic photocatalysts. The process features free metal-complex photocatalysts, acids, and mild reaction conditions. This mild radical cyclization protocol has a broad substrate scope and can be effectively applied to a variety of medicinally relevant substrates. Furthermore, control experiments were conducted to elucidate the mechanism of this visible light-induced methodology.

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Sulfonyl Radical-Induced Regioselective Cyclization of Enamide–Olefin To Form Sulfonylated 6–7-Membered Cyclic Enamines

Ding,

Gang,

Tang

et al. 2024

J. Org. Chem.

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Remarkable progress has been made in the radical cascade cyclization of heteroaryl-or aryl-tethered alkenes to construct benzene-fused frameworks via the cracking of aryl C−H bonds. In contrast, the radical cascade cyclization of linear dienes through the cracking of vinyl C−H bonds to construct nonbenzene-fused ring frameworks with endocyclic double bonds has significantly lagged behind, and major advances have largely been restricted to the generation of 5-membered heterocycles, such as pyrrolinones. Herein, we report the silver-mediated regioselective sulfonylation-cyclization of linear dienes with sodium sulfinates to form sulfonylated 6and 7-membered cyclic enamines.

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Palladium catalyzed tandem cyclization of acryloylbenzamides and N-arylacrylamides with epoxides: access to functionalized isoquinolinediones and oxindoles

Abstract: Herein, a practical and efficient tandem cyclization ring-opening coupling of acryloylbenzamides and N-arylacrylamides with epoxides is reported.

Cited by 5 publications

References 84 publications

Recent advances in constructing efficient materials for electrocatalytic oxidation of propylene

Recent advances in constructing efficient materials for electrocatalytic oxidation of propylene

Photocatalytic Proton-Coupled Electron Transfer Enabled Radical Cyclization for Isoquinoline-1,3-diones Synthesis

Sulfonyl Radical-Induced Regioselective Cyclization of Enamide–Olefin To Form Sulfonylated 6–7-Membered Cyclic Enamines

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