Issue 24, 2020

General and efficient synthesis of 1,2-dihydropyrrolo[3,4-b]indol-3-ones via a formal [3 + 2] cycloaddition initiated by C–H activation

Abstract

A [Cp*RhCl2]2-catalyzed formal [3 + 2] cycloaddition between isocyanates and indoles with electron-deficient alkenes at the C3-position of the indole moiety and directing groups at the N1-position of the indole moiety has been described. Undergoing sequential coupling reaction initiated by C–H activation and aza-Michael addition, a series of 1,2-dihydropyrrolo[3,4-b]indol-3-ones were successfully afforded in moderate to good yields by the formation of one C–C bond and one C–N bond. Interestingly, the pyridyl group at the N1-position of the indole moiety not only plays a role as the directing group, but also catalyses further intramolecular Michael addition as a base.

Graphical abstract: General and efficient synthesis of 1,2-dihydropyrrolo[3,4-b]indol-3-ones via a formal [3 + 2] cycloaddition initiated by C–H activation

Supplementary files

Article information

Article type
Research Article
Submitted
03 Aug 2020
Accepted
22 Oct 2020
First published
23 Oct 2020

Org. Chem. Front., 2020,7, 4057-4063

General and efficient synthesis of 1,2-dihydropyrrolo[3,4-b]indol-3-ones via a formal [3 + 2] cycloaddition initiated by C–H activation

S. Xing, J. Guo, Y. Wang, C. Wang, K. Wang and B. Zhu, Org. Chem. Front., 2020, 7, 4057 DOI: 10.1039/D0QO00922A

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