Carbonylative Synthesis of Fused Quinoxalinones via Palladium-Catalyzed Cascade Cyclization of 2-Heteroaryl Iodobenzene and NaN<sub>3</sub>

Song, Yu‐Fei; Quan, Zhaolin; Chen, Zhengkai; Wu, Xiao‐Feng

doi:10.1021/acs.orglett.3c01466

Cited by 5 publications

(2 citation statements)

References 31 publications

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“…So, Many researchers extensively studied carbonylation processes for heterocycle synthesis [35–40] . Several authors have recently reviewed the cyclo‐carbonylation reaction that gives rise to a simple lactone and lactam ring with five, six, and seven members [41–50] .…”

Section: Catalytic Carbonylation Via Homogeneous Catalytic Routementioning

confidence: 99%

“…So, Many researchers extensively studied carbonylation processes for heterocycle synthesis. [35][36][37][38][39][40] Several authors have recently reviewed the cyclo-carbonylation reaction that gives rise to a simple lactone and lactam ring with five, six, and seven members. [41][42][43][44][45][46][47][48][49][50] This section explained the synthesis of α, βalkynyl ketones, coumarin, 2-quinolone, indol derivative, furane derivative, and chromenone heterocyclic compound from homogenous palladium-catalyzed carbonylation reaction.…”

Section: Synthesis Of Heterocyclic Compoundsmentioning

confidence: 99%

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A Review of Synthetic Application of Homogeneous, Heterogenised‐Homogeneous, and Microwave‐Assisted Catalytic Carbonylation of Selected Substrates

Pant,

Prakash,

Dhami

2024

ChemistrySelect

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Catalytic carbonylation has gained a lot of interest over the past 20 years. It produced various pharmaceuticals, agrochemicals, and intermediates that can made through this process. The carbonylation process is the most straightforward method to insert CO into any organic substrate using a simple carbonyl source, i. e., CO gas. Apart from gaseous CO, many techniques have devised for producing CO in situ using surrogates such as HCOOH, DMF, Formic acid, Phenyl Formate, Oxalic acid, and Chloroform. Several carbonylation methods, such as aminocarbonylation, alkoxycarbonylation, double carbonylation, and oxidative carbonylation, provide viable and appealing substitutes for conventional synthetic methods on a commercial or laboratory scale. Many recent studies focus on catalyst‐product separation, catalyst recoverability, and reusability in these reactions. Therefore, advancements in using different approaches, such as supported liquid phase catalysis and biphasic catalysis, to anchor homogeneous catalysts are becoming increasingly important. These carbonylation methods are easy to use, cost‐effective, and do not require ligands. They also produce excellent yields of the products necessary. Using phosphine ligands has drawbacks, including high work‐up costs, laborious work‐up techniques, and sensitivity to air and moisture. Several phosphine‐free carbonylation pathways offer affordable and straightforward ways to accomplish these changes without phosphine ligands. This review summarizes the synthetic application of homogeneous and immobilized catalysts in producing carboxylic acid derivatives and heterocycles that have medicinal properties.

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Section: Catalytic Carbonylation Via Homogeneous Catalytic Routementioning

confidence: 99%

Section: Synthesis Of Heterocyclic Compoundsmentioning

confidence: 99%

A Review of Synthetic Application of Homogeneous, Heterogenised‐Homogeneous, and Microwave‐Assisted Catalytic Carbonylation of Selected Substrates

Pant,

Prakash,

Dhami

2024

ChemistrySelect

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Palladium-Catalyzed Carbonylative Cyclization of 1-Alkynyl-2-iodo-d-glucal

Hornink,

Figlino,

Toledo

et al. 2024

Org. Lett.

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Cascade reactions are important synthetic tools for the synthesis of heterocyclic molecules, particularly those catalyzed by palladium. Herein, we report a palladium-catalyzed aminocarbonylative cyclization of new 1-alkynyl-2-iodo-D-glucals, which undergo a tandem carbonylative cyclization in the presence of various amine nucleophiles. A broad range of aromatic and aliphatic amines were applied as coupling partners, resulting in the selective and high-yield synthesis of glycosides fused to pyridinones. A plausible mechanism is proposed, proceeding via a tandem palladium aminocarbonylation followed by a palladium-catalyzed endo-dig cyclization.

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Site-Selective Access to Functionalized Pyrroloquinoxalinones via H-Atom Transfer from N═C_sp²–H Bonds of Quinoxalinones

Qu,

Li,

Liu

et al. 2024

Org. Lett.

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Site-selective hydrogen atom transfer (HAT) from the N�C sp 2 −H bonds of quinoxaline-2(1H)-ones is a highly attractive but underdeveloped domain. Reported herein is a highly selective, practical, and economically efficient approach for facile assembly of pyrroloquinoxalinones by synergistic photocatalysis and HAT catalysis. The reaction proceeds through bromine radicalmediated HAT of quinoxalinones and imine radical addition to α-cyano-α,β-unsaturated ketones that establishes a cross-coupling/ annulation cascade process, resulting in the synthesis of a series of functionalized pyrroloquinoxalinones. This protocol does not require transition metals or excess oxidants and uses easy-to-synthesize starting materials with excellent scalability and broad substrate scope. The establishment of N�C sp 2 radical chemistry illustrates great potential for the synthesis of imine-containing molecules that are not possible with some traditional methods.

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Carbonylative Synthesis of Fused Quinoxalinones via Palladium-Catalyzed Cascade Cyclization of 2-Heteroaryl Iodobenzene and NaN₃

Cited by 5 publications

References 31 publications

A Review of Synthetic Application of Homogeneous, Heterogenised‐Homogeneous, and Microwave‐Assisted Catalytic Carbonylation of Selected Substrates

A Review of Synthetic Application of Homogeneous, Heterogenised‐Homogeneous, and Microwave‐Assisted Catalytic Carbonylation of Selected Substrates

Palladium-Catalyzed Carbonylative Cyclization of 1-Alkynyl-2-iodo-d-glucal

Site-Selective Access to Functionalized Pyrroloquinoxalinones via H-Atom Transfer from N═C_sp²–H Bonds of Quinoxalinones

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Carbonylative Synthesis of Fused Quinoxalinones via Palladium-Catalyzed Cascade Cyclization of 2-Heteroaryl Iodobenzene and NaN3

Cited by 5 publications

References 31 publications

A Review of Synthetic Application of Homogeneous, Heterogenised‐Homogeneous, and Microwave‐Assisted Catalytic Carbonylation of Selected Substrates

A Review of Synthetic Application of Homogeneous, Heterogenised‐Homogeneous, and Microwave‐Assisted Catalytic Carbonylation of Selected Substrates

Palladium-Catalyzed Carbonylative Cyclization of 1-Alkynyl-2-iodo-d-glucal

Site-Selective Access to Functionalized Pyrroloquinoxalinones via H-Atom Transfer from N═Csp2–H Bonds of Quinoxalinones

Contact Info

Product

Resources

About

Carbonylative Synthesis of Fused Quinoxalinones via Palladium-Catalyzed Cascade Cyclization of 2-Heteroaryl Iodobenzene and NaN₃

Site-Selective Access to Functionalized Pyrroloquinoxalinones via H-Atom Transfer from N═C_sp²–H Bonds of Quinoxalinones