Issue 26, 2023

Trimethylindolenines as C–N synthons for the assembly of spiro[oxindole-thioxoimidazolidine-indoline] hybrids in formal [3+2] cycloadditions

Abstract

Herein, previously unreported trimethylindolenines serving as useful C–N synthons in [3+2] cycloaddition reactions of donor–acceptor 3-isothiocyanato oxindoles to build a library of spiro[oxindole-thioxoimidazolidine-indoline] hybrids are described. A wide range of intriguing and complex products bearing three pharmacophores and three adjacent quaternary stereocentres were smoothly afforded in up to 92% yield, >20 : 1 dr, under catalyst-free conditions. Moreover, this strategy further expands the skeletal diversity of polyheterocycles, which will aid the search for new bioactive molecules.

Graphical abstract: Trimethylindolenines as C–N synthons for the assembly of spiro[oxindole-thioxoimidazolidine-indoline] hybrids in formal [3+2] cycloadditions

Supplementary files

Article information

Article type
Paper
Submitted
27 Feb 2023
Accepted
31 May 2023
First published
31 May 2023

New J. Chem., 2023,47, 12296-12303

Trimethylindolenines as C–N synthons for the assembly of spiro[oxindole-thioxoimidazolidine-indoline] hybrids in formal [3+2] cycloadditions

W. Zhang, Z. Chen, R. Liu, X. Liu, B. Pan, J. Zhou, Y. Zhou, Y. Tian and X. Liu, New J. Chem., 2023, 47, 12296 DOI: 10.1039/D3NJ00901G

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