Synthesis of 2,4-Diarylquinoline Derivatives via Chloranil-Promoted Oxidative Annulation and One-Pot Reaction

Cheng, Dongping; Yan, Xianhang; Shen, Jing; Pu, Yueqi; Xu, Xinhua; Yan, Jizhong

doi:10.1055/s-0039-1691740

Cited by 9 publications

(1 citation statement)

References 12 publications

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“…The various 4-chloro- [1,2,4]triazolo [4,3a]quinoxaline intermediates substituted in position 1 are obtained after purifications, with yields ranging from 47% to 86%. Chloranil, a tetrachlorinated derivative of quinone, is a mild commercial oxidant that allows for the formation of complex heterocycles with good yields [84]. A hypothetical mechanism for the formation of [1,2,4]triazolo [4,3-a]quinoxaline has been proposed by V. Krishnan [83].…”

Section: Selected General Chemical Strategy and Diversificationmentioning

confidence: 99%

[1,2,4]triazolo[4,3-a]quinoxaline as Novel Scaffold in the Imiqualines Family: Candidates with Cytotoxic Activities on Melanoma Cell Lines

Patinote,

Raevens,

Baumann

et al. 2023

Molecules

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Cutaneous melanoma is one of the most aggressive human cancers and is the deadliest form of skin cancer, essentially due to metastases. Novel therapies are always required, since cutaneous melanoma develop resistance to oncogenic pathway inhibition treatment. The Imiqualine family is composed of heterocycles diversely substituted around imidazo[1,2-a]quinoxaline, imidazo[1,2-a]pyrazine, imidazo[1,5-a]quinoxaline, and pyrazolo[1,5-a]quinoxaline scaffolds, which display interesting activities on a panel of cancer cell lines, especially melanoma cell lines. We have designed and prepared novel compounds based on the [1,2,4]triazolo[4,3-a]quinoxaline scaffold through a common synthetic route, using 1-chloro-2-hydrazinoquinoxaline and an appropriate aldehyde. Cyclization is ensured by an oxidation-reduction mechanism using chloranil. The substituents on positions 1 and 8 were chosen based on previous structure–activity relationship (SAR) studies conducted within our heterocyclic Imiqualine family. Physicochemical parameters of all compounds have also been predicted. A375 melanoma cell line viability has been evaluated for 16 compounds. Among them, three novel [1,2,4]triazolo[4,3-a]quinoxalines display cytotoxic activities. Compounds 16a and 16b demonstrate relative activities in the micromolar range (respectively, 3158 nM and 3527 nM). Compound 17a shows the best EC50 of the novel series (365 nM), even if EAPB02303 remains the lead of the entire Imiqualine family (3 nM).

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Section: Selected General Chemical Strategy and Diversificationmentioning

confidence: 99%

[1,2,4]triazolo[4,3-a]quinoxaline as Novel Scaffold in the Imiqualines Family: Candidates with Cytotoxic Activities on Melanoma Cell Lines

Patinote,

Raevens,

Baumann

et al. 2023

Molecules

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Fe‐Catalyzed, Solvent‐Controlled, Switchable Routes for the Domino Construction of 2,4‐Disubstituted and 4‐Substituted Quinoline Scaffolds

Jagtap,

Sawant,

Bhanage

2024

ChemCatChem

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In this report, we unveil a highly efficient novel protocol for the domino synthesis of 2,4‐disubstituted and 4‐substituted quinoline scaffolds. The developed strategy involves earth‐abundant Fe‐catalyzed, solvent‐controlled, switchable routes for the selective construction of 2,4‐disubstituted and 4‐substituted quinoline frameworks, achieved by using either trifluoroethanol (TFE) or methanol (MeOH) as a solvent. By employing TFE as a solvent in Path A, the alkyne itself serves as a dual synthon through Fe‐catalyzed in situ C(sp)‐C(sp) bond cleavage, enabling the synthesis of two important molecules: 2,4‐disubstituted and 4‐substituted quinolines. Later, upon switching the reaction medium from TFE to MeOH for Path‐B, only 4‐substituted quinolines were obtained extensively. In this Path‐B, Fe‐catalyzed oxidation of methanol was observed and here methanol functioned as both a solvent and an environmentally benign carbon source. Both of these strategies were utilized to prepare a broad range of mono‐ and di‐substituted quinoline derivatives. In the application section and for practical utility, the scale‐up studies, along with the photophysical properties of the synthesized quinoline moiety are also demonstrated.

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2,3‐Dichloro‐5,6‐dicyano‐1,4‐benzoquinone (DDQ)‐Mediated Tandem Oxidative Annulation for Preparing 2,2‐Disubstituted 2,3‐Dihydroquinazolin‐4(1H)‐ones

Cheng

Yan

et al. 2021

Eur J Org Chem

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An efficient tandem oxidative annulation for the synthesis of 2,2‐disubstituted 2,3‐dihydroquinazolin‐4(1H)‐ones via DDQ‐mediated dual cross‐dehydrogenative‐coupling (CDC) reactions is described. This transformation proceeds from easily available o‐aminobenzamides and 1,3‐diarylpropenes under mild conditions, and the corresponding products are obtained in moderate to excellent yields.

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Synthesis of 2,4-Diarylquinoline Derivatives via Chloranil-Promoted Oxidative Annulation and One-Pot Reaction

Cited by 9 publications

References 12 publications

[1,2,4]triazolo[4,3-a]quinoxaline as Novel Scaffold in the Imiqualines Family: Candidates with Cytotoxic Activities on Melanoma Cell Lines

[1,2,4]triazolo[4,3-a]quinoxaline as Novel Scaffold in the Imiqualines Family: Candidates with Cytotoxic Activities on Melanoma Cell Lines

Fe‐Catalyzed, Solvent‐Controlled, Switchable Routes for the Domino Construction of 2,4‐Disubstituted and 4‐Substituted Quinoline Scaffolds

2,3‐Dichloro‐5,6‐dicyano‐1,4‐benzoquinone (DDQ)‐Mediated Tandem Oxidative Annulation for Preparing 2,2‐Disubstituted 2,3‐Dihydroquinazolin‐4(1H)‐ones

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