A Novel One-Pot Green Synthesis of Dispirooxindolo-pyrrolidines via 1,3-Dipolar Cycloaddition Reactions of Azomethine Ylides

A facile synthesis of dispirooxindolopyrrolidines has been accomplished via a one-pot three component 1,3-dipolar cycloaddition reaction. The reaction of azomethine ylides generated in situ from L-phenylalanine and substituted isatins with a series of unusual (E)-2-oxoindolino-3-ylidene acetophenone...

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Published inMolecules (Basel, Switzerland) Vol. 20; no. 1; pp. 780 - 791
Main Authors Almansour, Abdulrahman, Arumugam, Natarajan, Kumar, Raju, Periyasami, Govindasami, A. Ghabbour, Hazem, Fun, Hoong-Kun
Format Journal Article
LanguageEnglish
Published Switzerland MDPI AG 07.01.2015
Subjects
1,3-dipolar cycloaddition
Azo Compounds - chemistry
azomethine ylide
Brain cancer
Cell cycle
Chemistry
Crystallography, X-Ray
Cycloaddition Reaction
dispiropyrrolidines
Investigations
ionic liquids
Magnetic Resonance Spectroscopy
Models, Molecular
Natural products
Pyrrolidines - chemical synthesis
Solvents
Spectrometry, Mass, Electrospray Ionization
Spectrophotometry, Infrared
Thiosemicarbazones - chemistry
VOCs
Volatile organic compounds
Saudi Arabia
Riyadh Saudi Arabia
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Summary:A facile synthesis of dispirooxindolopyrrolidines has been accomplished via a one-pot three component 1,3-dipolar cycloaddition reaction. The reaction of azomethine ylides generated in situ from L-phenylalanine and substituted isatins with a series of unusual (E)-2-oxoindolino-3-ylidene acetophenone dipolarophiles in the ionic liquid 1-butyl-3-methylimidazolium bromide [bmim]BF4, furnished the cycloadducts in good yields, with the regioisomers 5a–f being obtained with high selectivity. Furthermore, the recyclability of [bmim]BF4, up to five times, was also investigated.
Bibliography:ObjectType-Article-1
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ISSN:1420-3049
1420-3049
DOI:10.3390/molecules20010780