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Access and Modulation of Substituted Pyrrolo[3,4-c]pyrazole-4,6-(2H,5H)-diones.

ABSTRACT: The first access to polyfunctionnalized pyrrolo[3,4-c]pyrazole-4,6-(2H,5H)-dione derivatives is reported. The series were generated from diethyl acetylenedicarboxylate and arylhydrazines, which afforded the key intermediates bearing two functional positions. The annellation to generate the maleimide moiety of the bicycle was studied. Moreover, an efficient palladium-catalyzed C-C and C-N bond formation via Suzuki-Miyaura or Buchwald-Hartwig coupling reactions in C-6 position was investigated from 6-chloropyrrolo[3,4-c]pyrazole-4,6-(2H,5H)-diones. This method provides novel access to various 1,6 di-substituted pyrrolo[3,4-c] pyrazole-4,6-(2H,5H)-diones.

SUBMITTER: Ejjoummany A

PROVIDER: S-EPMC10421423 | biostudies-literature | 2023 Aug

REPOSITORIES: biostudies-literature

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Access and Modulation of Substituted Pyrrolo[3,4-c]pyrazole-4,6-(2H,5H)-diones.

Ejjoummany Abdelaziz A Elie Jonathan J El Hakmaoui Ahmed A Akssira Mohamed M Routier Sylvain S Buron Frédéric F

Molecules (Basel, Switzerland) 20230801 15

The first access to polyfunctionnalized pyrrolo[3,4-c]pyrazole-4,6-(2H,5H)-dione derivatives is reported. The series were generated from diethyl acetylenedicarboxylate and arylhydrazines, which afforded the key intermediates bearing two functional positions. The annellation to generate the maleimide moiety of the bicycle was studied. Moreover, an efficient palladium-catalyzed C-C and C-N bond formation via Suzuki-Miyaura or Buchwald-Hartwig coupling reactions in C-6 position ...[more]

PMID: 37570778

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