Cyclocondensation of coumarin-3-thioformates with 3-hydroxyoxindoles and 3-aminooxindoles for the synthesis of spiro-fused pentaheterocyclic compounds. Issue 3 (3rd January 2020)

• Record Type: Journal Article
• Authors: Lei, Chuan-Wen; Zhang, Chuan-Bao; Wang, Zhen-Hua; Xie, Ke-Xin; Zhao, Jian-Qiang; Zhou, Ming-Qiang; Zhang, Xiao-Mei; Xu, Xiao-Ying; Yuan, Wei-Cheng
• Is Part Of: Organic chemistry frontiers. Volume 7:Issue 3(2020)
• Page Start: 499
• Page End: 506
• Publication Date: 2020-01-03
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/c9qo01039d
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : A range of spiro-fused pentaheterocyclic compounds including spiro-butyrolactoneoxindole[3, 4- c ]coumarins and spiro-butyrolactamoxindole[3, 4- c ]coumarins were smoothly obtained via tandem Michael addition-lactonization/lactamization process. 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 Et3 N 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.