Solid‐Phase Synthesis of 3,4‐Dihydroquinoxalin‐2(1H)‐ones via the Cyclative Cleavage of N‐Arylated Carboxamides

Carbain, Benoît; Schütznerová, Eva; Přibylka, Adam; Krchňák, Viktor

doi:10.1002/adsc.201500826

Cited by 11 publications

(3 citation statements)

References 34 publications

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“…We developed a practical route for the synthesis of diverse derivatives of tetramic acid, a natural product with a broad range of pharmacologically relevant activities. We exploited the advantages of SP synthesis and designed the synthesis in a modular fashion using simple building blocks and user‐friendly reaction conditions following a strategy we frequently use for the synthesis of diverse heterocycles . To assess the feasibility of this synthetic route, we first prepared acyclic resin‐bound precursor 5 .…”

Section: Resultsmentioning

confidence: 99%

Solid‐Phase Synthesis of Tetramic Acid via Resin‐Bound Enol Ethers as a Privileged Scaffold in Drug Discovery

et al. 2018

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This paper reports the practical synthesis of a tetramic acid scaffold on solid phase using simple, commercially available building blocks under mild conditions. Acyclic precursors were assembled on solid phase in four steps, and cyclization was achieved by Wittig olefination. The target compounds contained three points of diversification and allowed for further modifications while still being attached to the resin. Solidphase synthesis represents a method of choice, particularly for parallel synthesis, because the intermediates can be isolated simply and quickly by washing the resin beads, which typically takes only minutes.

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Section: Resultsmentioning

confidence: 99%

Solid‐Phase Synthesis of Tetramic Acid via Resin‐Bound Enol Ethers as a Privileged Scaffold in Drug Discovery

et al. 2018

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“…As a part of their study on 2-nitrobenzensulfonamides as advanced intermediates for the synthesis of diverse classes of heterocycles, Krchňák et al developed a method to synthesize 3,4-dihydroquinoxalin-2(1 H )-ones . Linear precursors were synthesized on Wang resin 2 (Scheme ) with an ethanolamine linker from Fmoc-amino acids, 2-nitrobenzensulfonyl chlorides, and alcohols.…”

Section: Cyclative Cleavagementioning

confidence: 99%

Traceless Solid-Phase Organic Synthesis

2019

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Traceless solid-phase synthesis represents an ultimate sophisticated synthetic strategy on insoluble supports. Compounds synthesized on solid supports can be released without a trace of the linker that was used to tether the intermediates during the synthesis. Thus, the target products are composed only of the components (atoms, functional groups) inherent to the target core structure. A wide variety of synthetic strategies have been developed to prepare products in a traceless manner, and this review is dedicated to all aspects of traceless solid-phase organic synthesis. Importantly, the synthesis does not need to be carried out on a linker designed for traceless synthesis; most of the synthetic approaches described herein were developed using standard, commercially available linkers (originally devised for solid-phase peptide synthesis). The type of structure prepared in a traceless fashion is not restricted. The individual synthetic approaches are divided into eight sections, each devoted to a different methodology for traceless synthesis. Each section consists of a brief outline of the synthetic strategy followed by a description of individual reported syntheses.

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“…Dihydroquinoxalinones are bioactive compounds of high interest, due to their anticancer [ 42 , 43 , 44 ] and anti-inflammatory [ 45 ] properties, as well as their activity against neurological diseases [ 46 ] ( Scheme 2 ). Dihydroquinaxolinone derivatives have been mainly synthesized via coupling of o -nitroaryl- or o -aminoaryl halides with amino acids [ 43 , 45 , 47 , 48 , 49 , 50 , 51 , 52 , 53 , 54 ], or transition metal-catalyzed asymmetric hydrogenation of the corresponding quinoxaline derivatives ( Scheme 2 ) [ 55 , 56 , 57 , 58 , 59 , 60 , 61 , 62 , 63 ]. However, these methods required air-sensitive catalysts, toxic organic solvents, and several ligands.…”

Section: Introductionmentioning

confidence: 99%

Supported Gold Nanoparticle-Catalyzed Selective Reduction of Multifunctional, Aromatic Nitro Precursors into Amines and Synthesis of 3,4-Dihydroquinoxalin-2-Ones

et al. 2022

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The synthesis of 3,4-dihydroquinoxalin-2-ones via the selective reduction of aromatic, multifunctional nitro precursors catalyzed by supported gold nanoparticles is reported. The reaction proceeds through the in situ formation of the corresponding amines under heterogeneous transfer hydrogenation of the initial nitro compounds catalyzed by the commercially available Au/TiO2-Et3SiH catalytic system, followed by an intramolecular C-N transamidation upon treatment with silica acting as a mild acid. Under the present conditions, the Au/TiO2-TMDS system was also found to catalyze efficiently the present selective reduction process. Both transfer hydrogenation processes showed very good functional-group tolerance and were successfully applied to access more structurally demanding products bearing other reducible moieties such as chloro, aldehyde or methyl ketone. An easily scalable (up to 1 mmol), low catalyst loading (0.6 mol%) synthetic protocol was realized, providing access to this important scaffold. Under these mild catalytic conditions, the desired products were isolated in good to high yields and with a TON of 130. A library analysis was also performed to demonstrate the usefulness of our synthetic strategy and the physicochemical profile of the derivatives.

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Solid‐Phase Synthesis of 3,4‐Dihydroquinoxalin‐2(1H)‐ones via the Cyclative Cleavage of N‐Arylated Carboxamides

Cited by 11 publications

References 34 publications

Solid‐Phase Synthesis of Tetramic Acid via Resin‐Bound Enol Ethers as a Privileged Scaffold in Drug Discovery

Solid‐Phase Synthesis of Tetramic Acid via Resin‐Bound Enol Ethers as a Privileged Scaffold in Drug Discovery

Traceless Solid-Phase Organic Synthesis

Supported Gold Nanoparticle-Catalyzed Selective Reduction of Multifunctional, Aromatic Nitro Precursors into Amines and Synthesis of 3,4-Dihydroquinoxalin-2-Ones

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