Synthesis of quinoxaline derivatives <i>via</i> aromatic nucleophilic substitution of hydrogen

Zasada, Aleksandra Anna; Brześkiewicz, Jakub; Antoniak, Damian; Bechcicka, Małgorzata; Loska, Rafał; Mąkosza, Mieczysław

doi:10.1039/d2ob02016e

Cited by 3 publications

(3 citation statements)

References 69 publications

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Section: Introductionmentioning

confidence: 64%

“…Although there are many protocols reported for the synthesis of quinoxaline derivatives involving both heterogeneous and homogeneous catalysts such as ceric ammonium nitrate, hexa fluoro isopropanol, mono‐ammonium phosphate, di‐ammonium phosphate, TiO 2 −Pr−SO 3 H, Ga(OTf) 3, etc [21,37–41] . but we did not find any heterogeneous organocatalyst‐based one‐pot multicomponent protocol reported for the synthesis of indeno [1, 2‐b] quinoxalin‐11‐ylidenamine derivatives in the literature which motivated us to develop a green heterogeneous‐catalyst‐based protocol for the construction of indeno [1, 2‐b] quinoxalin‐11‐ylidenamines.…”

Section: Introductionmentioning

confidence: 92%

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[MTP−IL] as Mesoporous Heterogeneous Organocatalyst for the One‐Pot Synthesis of Indeno [1,2‐b] Quinoxalin‐11‐Ylidenamine Derivatives: A Green, Sustainable, and Metal‐Free Protocol

Mustafa,

Zameer,

Khan

et al. 2024

ChemistrySelect

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Herein, we report a green, sustainable, and metal‐free, one‐pot three‐component protocol for the synthesis of indeno [1, 2‐b] quinoxalin‐11‐ylidenamine derivatives using a novel, effective, and recyclable mesoporous heterogeneous organocatalyst [MTP−IL]. [MTP−IL] was constructed by immobilizing an imidazolium‐cation‐based ionic liquid on a melamine−terephthalaldehyde covalent organic polymer and was thoroughly characterized using several analytical techniques. It displayed high thermochemical stability and catalytic efficacy, offering title compounds with 90–94 % yields in a short reaction time, and was recyclable for up to six cycles. The synthesized compounds were characterized through FTIR, 1H, and 13C Nuclear Magnetic Resonance (NMR), and the molecular structure of N′‐(11H‐indeno[1,2‐b]quinoxalin‐11‐ylidene)benzohydrazide (7) was confirmed by the Single Crystal XRD (SCXRD) analysis. The key features of the present protocol are the use of ethanol as a green solvent, easy catalyst recovery, a simple work‐up procedure, and zero involvement of any metal.

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Section: Introductionmentioning

confidence: 64%

Section: Introductionmentioning

confidence: 92%

[MTP−IL] as Mesoporous Heterogeneous Organocatalyst for the One‐Pot Synthesis of Indeno [1,2‐b] Quinoxalin‐11‐Ylidenamine Derivatives: A Green, Sustainable, and Metal‐Free Protocol

Mustafa,

Zameer,

Khan

et al. 2024

ChemistrySelect

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“…In the reaction between chlorofluoroacetyl derivatives 81 and quinoxaline N‐oxides 80 under basic conditions, vicarious nucleophilic substitution takes place to access monofluorinated derivatives 82 (Scheme 33). [64] …”

Section: Fluoroacetyl Carbene Transfermentioning

confidence: 99%

Recent Advances in Monofluorinated Carbenes, Carbenoids, Ylides, and Related Species

Sperga,

Veliks

2023

Chemistry A European J

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The synthesis of monofluorinated compounds is of great interest because of the vast applications of organofluorine compounds. Recently, the introduction of monofluorocarbene synthons has emerged as an important strategy for the synthesis of fluorine‐containing products. In contrast to direct fluorination, in which C−F bonds are formed, the use of monofluorinated carbenes and related reactive species involves C−C or C−X bond formation while delivering valuable fluorine atoms into the target structure. Owing to increased knowledge on carbon‐carbon and carbon‐heteroatom bond formations, monofluorinated carbenes have enormous potential for the synthesis of organofluorine compounds, which, in our opinion, has not yet been fully exploited. This review summarizes the recent advances in the synthetic applications of monofluorinated carbenes, carbenoids, ylides, and related species.

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From Conventional to Sustainable Catalytic Approaches for Heterocycles Synthesis

Rizzo,

Pace,

Pibiri

et al. 2024

ChemSusChem

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Synthesis of heterocyclic compounds is fundamental for all the research area in chemistry, from drug synthesis to material science. In this framework, catalysed synthetic methods are of great interest to effective reach such important building blocks. In this review, we will report on some selected examples from the last five years, of the major improvement in the field, focusing on the most important conventional catalytic systems, such as transition metals, organocatalysts, to more sustainable ones such as photocatalysts, iodine‐catalysed reaction, electrochemical reactions and green innovative methods.

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Synthesis of quinoxaline derivatives via aromatic nucleophilic substitution of hydrogen

Abstract: Electrophilic nature of quinoxaline has been explored in the vicarious nucleophilic substitution of hydrogen (VNS) with various carbanions as nucleophiles, in the attempt to develop a general method of functionalizing...

Cited by 3 publications

References 69 publications

[MTP−IL] as Mesoporous Heterogeneous Organocatalyst for the One‐Pot Synthesis of Indeno [1,2‐b] Quinoxalin‐11‐Ylidenamine Derivatives: A Green, Sustainable, and Metal‐Free Protocol

[MTP−IL] as Mesoporous Heterogeneous Organocatalyst for the One‐Pot Synthesis of Indeno [1,2‐b] Quinoxalin‐11‐Ylidenamine Derivatives: A Green, Sustainable, and Metal‐Free Protocol

Recent Advances in Monofluorinated Carbenes, Carbenoids, Ylides, and Related Species

From Conventional to Sustainable Catalytic Approaches for Heterocycles Synthesis

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