Chromone-indanedione reactant: a bifunctional 3C synthon for diastereoselective construction of skeleton-diversified bispiro-[chromanocyclopentane-oxindole-indanedione]

• Published in: New journal of chemistry 2021-07, Vol.45 (28), p.12356-12361
• Main Authors: Zhou, Wei, Li, Zheng, Tian, You-Ping, Han, Xiao-Xue, Liu, Xiong-Li
• Format: Article
• Language: English
• Subjects: Crystallography; Cycloaddition; Precursors; Single crystals; Stereoselectivity; Substrates
• ISSN: 1144-0546; 1369-9261
• DOI: 10.1039/d1nj02257a

A new type of bifunctional 3C synthon, a chromone-indanedione precursor, was employed for diastereoselective Michael/Michael cycloaddition with methyleneindolinones to generate a series of potentially bioactive bispiro-[chromanocyclopentane-oxindole-indanedione] frameworks with skeletal diversity in a single operation. This reaction exhibited good substrate tolerance and gave the desired products in moderate to good yields with high diastereoselectivities via an endo -transition state (up to 78% yield and >20 : 1 diastereomeric ratio). In particular, this reaction is the first example of using a chromone-indanedione precursor as a bifunctional 3C synthon, the first example of the construction of bispiro-chromanocyclopentanes, and also the first example of the introduction of a chromanocyclopentane moiety into spiroindanone frameworks, which might be valuable in medicinal chemistry. A new type of bifunctional 3C synthon, a chromone-indanedione precursor, was employed for diastereoselective Michael/Michael cycloaddition with methyleneindolinones to generate a series of potentially bioactive bispiro-[chromanocyclopentane-oxindole-indanedione] frameworks with skeletal diversity in a single operation.