Diastereoselective synthesis of dispiro[indoline-3,3 '-furan-2 ',3 ''-pyrrolidine]via[3+2]cycloaddition reaction of MBH maleimides of isatins and 1,3-dicarbonyl compounds

In the presence of mixed bases DABCO and K2CO3, the reaction of MBH maleimides of isatins with various cyclic 1,3-dicarbonyl compounds such as 1,3-cyclohexanedione, dimedone, 4-hydroxychromenone and benzoylacetonitrile afforded functionalized dispiro[indoline-3,3 '-furan-2 ',3 ''...

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Published inORGANIC CHEMISTRY FRONTIERS Vol. 7; no. 20; pp. 3202 - 3208
Main Authors Pan, Liu-Na, Sun, Jing, Shi, Rong-Guo, Yan, Chao-Guo
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 21.10.2020
Royal Society of Chemistry
Subjects
Acrylonitrile
Adducts
Carbonyl compounds
Chemistry
Chemistry, Organic
Crystallography
Cycloaddition
NMR
Nuclear magnetic resonance
Organic chemistry
Physical Sciences
Potassium carbonate
Pyrrolidine
Science & Technology
Stereoselectivity
Substitution reactions
DOMINO REACTION
MDM2 INHIBITORS
4+1 ANNULATIONS
ENANTIOSELECTIVE SYNTHESIS
ANTICANCER
OXINDOLES
BAYLIS-HILLMAN CARBONATES
ADDUCTS
CYCLOADDITION REACTION
SPIROOXINDOLES
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Summary:In the presence of mixed bases DABCO and K2CO3, the reaction of MBH maleimides of isatins with various cyclic 1,3-dicarbonyl compounds such as 1,3-cyclohexanedione, dimedone, 4-hydroxychromenone and benzoylacetonitrile afforded functionalized dispiro[indoline-3,3 '-furan-2 ',3 ''-pyrrolidines] in satisfactory yields and with high diastereoselectivity. This formal [3 + 2]cycloaddition proceeded with nucleophilic substitution of an allylammonium ylide and oxa-Michael addition of an enolate. However, a similar reaction of MBH adducts of isatins derived from acrylonitrile and methyl acrylate resulted in functionalized spiro[indoline-3,4 '-pyranes] in good yields through formal [3 + 3]cycloaddition reaction.
ISSN:2052-4129
2052-4110
2052-4110
DOI:10.1039/d0qo00845a