Coumarin-3-formylpyrazoles as 3-carbon synthons in cyclocondensation for the synthesis of spiro-fused pentacyclic spirooxindoles. Issue 5 (14th 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 & biomolecular chemistry. Volume 18:Issue 5(2020)
• Page Start: 845
• Page End: 850
• Publication Date: 2020-01-14
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c9ob02434d
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : A range of spiro-fused pentacyclic spirooxindoles were smoothly obtained by using coumarin-3-formylpyrazoles as 3-carbon synthons via a tandem esterification/intramolecular Michael addition process. Abstract : Coumarin-3-formylpyrazoles have been synthesized and applied as 3-carbon synthons in reaction with 3-hydroxyoxindoles by using DABCO as the catalyst. A range of structurally diverse spiro-fused pentacyclic spirooxindoles, bearing a spirooxindole-γ-lactone and a 3, 4-dihydrocoumarin substructure, could be smoothly obtained in good to excellent yields (up to 99%) with excellent diastereoselectivities (all cases >20 : 1 dr). The asymmetric version of this tandem reaction was preliminarily investigated by using chiral organocatalysts.