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

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...

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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
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cited_by cdi_FETCH-LOGICAL-c211t-c77446d587037436fe97ad9beb144616aa763b2a3bd7faa04723ede39fc9c3d93
cites cdi_FETCH-LOGICAL-c211t-c77446d587037436fe97ad9beb144616aa763b2a3bd7faa04723ede39fc9c3d93
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container_issue 28
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container_title New journal of chemistry
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creator Zhou, Wei
Li, Zheng
Tian, You-Ping
Han, Xiao-Xue
Liu, Xiong-Li
description 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.
doi_str_mv 10.1039/d1nj02257a
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source Royal Society of Chemistry:Jisc Collections:Royal Society of Chemistry Read and Publish 2022-2024 (reading list)
subjects Crystallography
Cycloaddition
Precursors
Single crystals
Stereoselectivity
Substrates
title Chromone-indanedione reactant: a bifunctional 3C synthon for diastereoselective construction of skeleton-diversified bispiro-[chromanocyclopentane-oxindole-indanedione]
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