Issue 3, 2024

An umpolung strategy for chemoselective metal-free [4 + 2] annulation of azlactones: access to tetrahydro-β-carbolin 1,3-diketone frameworks

Abstract

A series of tetrahydro-β-carbolin 1,3-diketone frameworks can be synthesized under mild conditions utilizing azlactones and indole-2-ylamides. This highly efficient [4 + 2] annulation further broadens the application of azlactones derived from amino acids via the umpolung strategy in organic synthesis, featuring good compatibility. Furthermore, control experiments indicate that the addition of the oxidant DDQ could complete the homocoupling of azlactones without a metal mediator. Moreover, DFT computational calculations were performed to further elucidate the chemoselectivity of the reaction and a plausible mechanism is proposed to explain the reaction process.

Graphical abstract: An umpolung strategy for chemoselective metal-free [4 + 2] annulation of azlactones: access to tetrahydro-β-carbolin 1,3-diketone frameworks

Supplementary files

Article information

Article type
Research Article
Submitted
29 Jul 2023
Accepted
09 Dec 2023
First published
12 Dec 2023

Org. Chem. Front., 2024,11, 822-829

An umpolung strategy for chemoselective metal-free [4 + 2] annulation of azlactones: access to tetrahydro-β-carbolin 1,3-diketone frameworks

M. Wang, Z. Zheng, M. Chen, G. Zhan, J. Wang, Q. Yang and W. Huang, Org. Chem. Front., 2024, 11, 822 DOI: 10.1039/D3QO01184D

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