DABCO-Catalyzed Mono-/Diallylation of N -Unsubstituted Isatin N , N '-Cyclic Azomethine Imine 1,3-Dipoles with Morita-Baylis-Hillman Carbonates

Allylation of -unsubstituted isatin , '-cyclic azomethine imines with Morita-Baylis-Hillman carbonates in the presence of 1-10 mol% DABCO in DCM at room temperature, rapidly gave -allylated and , -diallylated isatin , '-cyclic azomethine imine 1,3-dipoles in moderate to high yields. The re...

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Published inMolecules (Basel, Switzerland) Vol. 28; no. 7; p. 3002
Main Authors Wang, Qiumi, Li, Sicheng, Yang, Guosheng, Zou, Xinyu, Yin, Xi, Feng, Juhua, Chen, Huabao, Yang, Chunping, Zhang, Li, Lu, Cuifen, Yue, Guizhou
Format Journal Article
LanguageEnglish
Published Switzerland MDPI AG 28.03.2023
MDPI
Subjects
Adducts
Alkylation
Allyl compounds
allylation
azomethine imine
Carbonates
Chemical reactions
Cycloaddition
dipole
Dipoles
Hydrocarbons
Imines
MBH carbonate
Room temperature
Solvents
cycloaddition
allylation
dipole
MBH carbonate
azomethine imine
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Summary:Allylation of -unsubstituted isatin , '-cyclic azomethine imines with Morita-Baylis-Hillman carbonates in the presence of 1-10 mol% DABCO in DCM at room temperature, rapidly gave -allylated and , -diallylated isatin , '-cyclic azomethine imine 1,3-dipoles in moderate to high yields. The reaction features mild reaction conditions, easily practical operation, and short reaction times in most cases. Furthermore, the alkylated products were transformed into novel bicyclic spiropyrrolidine oxoindole derivatives through the [3+2] or [3+3]-cycloaddition with maleimides or Knoevenagel adducts.
Bibliography:ObjectType-Article-1
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These authors contributed equally to this work.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules28073002