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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Bibliographic Details
Published in:Molecules (Basel, Switzerland) Switzerland), 2015-01, Vol.20 (1), p.780-791
Main Authors: Almansour, Abdulrahman I, Arumugam, Natarajan, Kumar, Raju Suresh, Periyasami, Govindasami, A Ghabbour, Hazem, Fun, Hoong-Kun
Format: Article
Language:English
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
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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.
ISSN:1420-3049
1420-3049
DOI:10.3390/molecules20010780