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PIDA-mediated intramolecular oxidative C-N bond formation for the direct synthesis of quinoxalines from enaminones.

ABSTRACT: A intramolecular oxidative C(sp²)-N bond formation mediated by hypervalent iodine(iii) to obtain quinoxalines from readily available N-(2-acetaminophenyl)enaminones was developed. A tandem process involving PIDA-mediated intramolecular condensation cyclization and a subsequent elimination was postulated, which was highly efficient and metal-free under mild conditions. Moreover, flexible structural modifications of quinoxalines bearing carbonyl groups are of interest for further transformations as building blocks in organic synthesis.

SUBMITTER: Zhang H

PROVIDER: S-EPMC9061175 | biostudies-literature | 2019 Mar

REPOSITORIES: biostudies-literature

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PIDA-mediated intramolecular oxidative C-N bond formation for the direct synthesis of quinoxalines from enaminones.

Zhang Hong H Shen Jinhai J Yang Zhenhui Z Cui Xiuling X

RSC advances 20190307 14

A intramolecular oxidative C(sp2)-N bond formation mediated by hypervalent iodine(iii) to obtain quinoxalines from readily available N-(2-acetaminophenyl)enaminones was developed. A tandem process involving PIDA-mediated intramolecular condensation cyclization and a subsequent elimination was postulated, which was highly efficient and metal-free under mild conditions. Moreover, flexible structural modifications of quinoxalines bearing carbonyl groups are of interest for further ...[more]

PMID: 35521175

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