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An efficient and facile access to highly functionalized pyrrole derivatives.

ABSTRACT: A straightforward and one-pot synthesis of pyrrolo[3,4-c]pyrrole-1,3-diones via Ag(I)-catalyzed 1,3-dipolar cycloaddition of azomethine ylides with N-alkyl maleimide, followed by readily complete oxidation with DDQ, has been successfully developed. Further transformation with alkylamine/sodium alkoxide alcohol solution conveniently afforded novel polysubstituted pyrroles in good to excellent yields. This methodology for highly functionalized pyrroles performed well over a broad scope of substrates. It is conceivable that this efficient construction method for privileged pyrrole scaffolds could deliver more active compounds for medicinal chemistry research.

SUBMITTER: Gao M

PROVIDER: S-EPMC5942380 | biostudies-literature | 2018

REPOSITORIES: biostudies-literature

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An efficient and facile access to highly functionalized pyrrole derivatives.

Gao Meng M Zhao Wenting W Zhao Hongyi H Lin Ziyun Z Zhang Dongfeng D Huang Haihong H

Beilstein journal of organic chemistry 20180420

A straightforward and one-pot synthesis of pyrrolo[3,4-c]pyrrole-1,3-diones via Ag(I)-catalyzed 1,3-dipolar cycloaddition of azomethine ylides with N-alkyl maleimide, followed by readily complete oxidation with DDQ, has been successfully developed. Further transformation with alkylamine/sodium alkoxide alcohol solution conveniently afforded novel polysubstituted pyrroles in good to excellent yields. This methodology for highly functionalized pyrroles performed well over a broad sco ...[more]

PMID: 29765469

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