Issue 3, 2020

Cyclocondensation of coumarin-3-thioformates with 3-hydroxyoxindoles and 3-aminooxindoles for the synthesis of spiro-fused pentaheterocyclic compounds

Abstract

Coumarin-3-thioformates acting as a new type of 3-carbon partner were firstly prepared and engaged in reacting with 3-hydroxyoxindoles and 3-aminooxindoles by using DABCO or Et3N as the catalyst. A wide scope of structurally diverse spiro-fused pentaheterocyclic compounds including spiro-butyrolactoneoxindole[3,4-c]coumarins and spiro-butyrolactamoxindole[3,4-c]coumarins, which combined oxindole, dihydrofuranone or pyrrolidone, and coumarin in one molecule, could be smoothly obtained in high yields via a tandem Michael addition–lactonization/lactamization process under mild conditions.

Graphical abstract: Cyclocondensation of coumarin-3-thioformates with 3-hydroxyoxindoles and 3-aminooxindoles for the synthesis of spiro-fused pentaheterocyclic compounds

Supplementary files

Article information

Article type
Research Article
Submitted
22 Aug 2019
Accepted
22 Dec 2019
First published
23 Dec 2019

Org. Chem. Front., 2020,7, 499-506

Cyclocondensation of coumarin-3-thioformates with 3-hydroxyoxindoles and 3-aminooxindoles for the synthesis of spiro-fused pentaheterocyclic compounds

C. Lei, C. Zhang, Z. Wang, K. Xie, J. Zhao, M. Zhou, X. Zhang, X. Xu and W. Yuan, Org. Chem. Front., 2020, 7, 499 DOI: 10.1039/C9QO01039D

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