Highly Selective Synthesis of 6-Glyoxylamidoquinoline Derivatives via Palladium-Catalyzed Aminocarbonylation

Chniti, Sami; Kollár, László; Bényei, Attila; Takács, Attila

doi:10.3390/molecules27010004

Cited by 4 publications

(1 citation statement)

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“…It is well documented that 6‐quinoline derivatives are important synthons for the preparation of central nervous system and anti‐asthmatic drugs. [ 81 ] In this regard, palladium‐catalyzed aminocarbonylation of 6‐iodoquinoline, recently described by Kollár, [ 82 ] is another paradigmatic example of the application of this reaction in the preparation of carboxamide and ketocarboxamide quinoline derivatives, catalyzed by Pd(OAc) 2 /xantphos (using 1 bar CO) or Pd(OAc) 2 /triphenylphosphine (using 40 bar CO pressure), respectively (Scheme 33).…”

Section: Synthesis Of Fine Chemicals Using Comentioning

confidence: 99%

Carbon Monoxide as C1 Building Block in Fine Chemical Synthesis^†

Carrilho,

Calvete,

Mikle

et al. 2023

Chin. J. Chem.

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Carbon monoxide (CO) has become one of the most relevant and versatile renewable C1 building blocks for chemical synthesis, especially in the fine chemicals industry, due to the development of efficient and selective catalysts for its activation. In this review, we present a comprehensive critical analysis of the last 10 years literature on the use of CO as a renewable feedstock for fine chemicals production. The review is organized by type of catalytic reaction, namely alkene and alkyne carbonylation, hydroformylation, carbonylation of aryl halides, carbonylative cross‐coupling and C–H carbonylation. Notable examples of the synthesis of relevant building blocks and/or known pharmaceuticals are highlighted. Emphasis is placed on examples of utilizing CO as the C1 building block in one or more catalytic steps. The catalyst used and the reaction conditions are consistently presented throughout all of the examples.This article is protected by copyright. All rights reserved.

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Section: Synthesis Of Fine Chemicals Using Comentioning

confidence: 99%

Carbon Monoxide as C1 Building Block in Fine Chemical Synthesis^†

Carrilho,

Calvete,

Mikle

et al. 2023

Chin. J. Chem.

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Palladium‐Catalyzed Aminocarbonylation of Heteroaryl Iodides

2022

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Palladium‐catalyzed aminocarbonylation of heteroaryl iodides is reported in the presence of chloroform as the carbon monoxide surrogate. The substrate scope of the reaction was demonstrated by the synthesis of quinoline‐3‐carboxamides and other heteroaryl amides in yields up to 90 % under non‐inert conditions and microwave irradiation at 80 °C in 30 min. This carbonylation method provides efficient access to previously inaccessible biologically important heteroaryl carboxamides.

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Synthesis of Chroman-2,4-diones via Ring-Opening/Ring-Closing Reaction Involving Palladium-Catalyzed Intramolecular Aryloxycarbonylation

Chniti,

Pongrácz,

Kollár

et al. 2024

J. Org. Chem.

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Palladium-catalyzed aminocarbonylation of 3-iodochromone was studied in the presence of primary and secondary amines using atmospheric pressure of carbon monoxide as a carbonyl source. This procedure successfully provided a library of chromone-3-carboxamides and 3-substituted chroman-2,4-diones in 40 to 92% isolated yields. The reaction proceeded via highly chemoselective aminocarbonylation (up to 100%) in the presence of secondary amines by using monodentate or bidentate phosphine ligands. The tendency of 3-iodochromone substrate to undergo ANRORC rearrangement with N-nucleophiles was crucial to shift the reaction toward an unprecedented chemoselective carbonylative transformation, where a late-stage carbonyl insertion is favored concomitantly to the last ring-closure step. The proposed aza-Michael addition/ring-opening/intramolecular aryloxycarbonylation sequence showed compatibility, uniquely, to primary amines when XantPhos was used as a ligand. The solid-state structures of chromone-3-carboxamide (2a) and chroman-2,4-dione (3s) were undoubtedly established by single-crystal XRD analysis. A catalytic cycle was proposed to rationalize the formation of the two types of carbonylated compounds.

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Highly Selective Synthesis of 6-Glyoxylamidoquinoline Derivatives via Palladium-Catalyzed Aminocarbonylation

Cited by 4 publications

References 88 publications

Carbon Monoxide as C1 Building Block in Fine Chemical Synthesis^†

Carbon Monoxide as C1 Building Block in Fine Chemical Synthesis^†

Palladium‐Catalyzed Aminocarbonylation of Heteroaryl Iodides

Synthesis of Chroman-2,4-diones via Ring-Opening/Ring-Closing Reaction Involving Palladium-Catalyzed Intramolecular Aryloxycarbonylation

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Highly Selective Synthesis of 6-Glyoxylamidoquinoline Derivatives via Palladium-Catalyzed Aminocarbonylation

Cited by 4 publications

References 88 publications

Carbon Monoxide as C1 Building Block in Fine Chemical Synthesis†

Carbon Monoxide as C1 Building Block in Fine Chemical Synthesis†

Palladium‐Catalyzed Aminocarbonylation of Heteroaryl Iodides

Synthesis of Chroman-2,4-diones via Ring-Opening/Ring-Closing Reaction Involving Palladium-Catalyzed Intramolecular Aryloxycarbonylation

Contact Info

Product

Resources

About

Carbon Monoxide as C1 Building Block in Fine Chemical Synthesis^†

Carbon Monoxide as C1 Building Block in Fine Chemical Synthesis^†