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Highly Stereoselective Ugi/Pictet-Spengler Sequence.

ABSTRACT: Discovering novel synthetic routes for rigid nitrogen-containing polyheterocycles using sustainable, atom-economical, and efficient (= short) synthetic pathways is of high interest in organic chemistry. Here, we describe an operationally simple and short synthesis of the privileged scaffold dihydropyrrolo[1,2-a]pyrazine-dione from readily accessible starting materials. The alkaloid-type polycyclic scaffold with potential bioactivity was achieved by a multicomponent reaction (MCR)-based protocol via a Ugi four-component reaction and Pictet-Spengler sequence under different conditions, yielding a diverse library of products.

SUBMITTER: Zhang B

PROVIDER: S-EPMC9490873 | biostudies-literature | 2022 Jun

REPOSITORIES: biostudies-literature

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Highly Stereoselective Ugi/Pictet-Spengler Sequence.

Zhang Bidong B Kurpiewska Katarzyna K Dömling Alexander A

The Journal of organic chemistry 20220512 11

Discovering novel synthetic routes for rigid nitrogen-containing polyheterocycles using sustainable, atom-economical, and efficient (= short) synthetic pathways is of high interest in organic chemistry. Here, we describe an operationally simple and short synthesis of the privileged scaffold dihydropyrrolo[1,2-<i>a</i>]pyrazine-dione from readily accessible starting materials. The alkaloid-type polycyclic scaffold with potential bioactivity was achieved by a multicomponent reaction (MCR)-based pr ...[more]

PMID: 35549475

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