A DBU-catalyzed Michael–Pinner–isomerization cascade reaction of 3-hydroxyoxindoles with isatylidene malononitriles: access to highly functionalized bispirooxindoles containing a fully substituted dihydrofuran motif. Issue 4 (9th January 2017)

• Record Type: Journal Article
• Authors: Zhu, Yan-Shuo; Wang, Wen-Bo; Yuan, Bei-Bei; Li, Ya-Ning; Wang, Qi-Lin; Bu, Zhan-Wei
• Is Part Of: Organic & biomolecular chemistry. Volume 15:Issue 4(2017)
• Page Start: 984
• Page End: 990
• Publication Date: 2017-01-09
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c6ob02254e
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : The first DBU-catalyzed Michael/Pinner/isomerization cascade reaction of 3-hydrooxindoles with isatylidene malononitriles was developed. Abstract : The first DBU-catalyzed Michael/Pinner/isomerization cascade reaction of 3-hydrooxindoles with isatylidene malononitriles was developed, and the corresponding highly functionalized bispirooxindoles containing a fully substituted dihydrofuran motif were obtained in up to 92% yields. This protocol also provides an efficient method for the synthesis of an α-cyano-γ-butyrolactone bispirooxindole. In addition, a one-pot three-component cascade reaction was conducted. Also, the asymmetric version of the cascade reaction was achieved.