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Molecules 2015, 20(1), 780-791; doi:10.3390/molecules20010780

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

Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia
Centro de Química-Física Molecular and Institute of Nanoscience and Nanotechnology, Instituto Superior Técnico, Universidade de Lisboa, Lisboa 1049-001, Portugal
Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi Arabia
Crystallography Unit, School of Physics, Universiti Sains Malaysia, Penang 11800, Malaysia
Author to whom correspondence should be addressed.
Academic Editor: Panayiotis A. Koutentis
Received: 1 December 2014 / Accepted: 30 December 2014 / Published: 7 January 2015
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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 5af being obtained with high selectivity. Furthermore, the recyclability of [bmim]BF4, up to five times, was also investigated. View Full-Text
Keywords: 1,3-dipolar cycloaddition; azomethine ylide; dispiropyrrolidines; ionic liquids 1,3-dipolar cycloaddition; azomethine ylide; dispiropyrrolidines; ionic liquids

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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Almansour, A.I.; Arumugam, N.; Kumar, R.S.; Periyasami, G.; A. Ghabbour, H.; Fun, H.-K. A Novel One-Pot Green Synthesis of Dispirooxindolo-pyrrolidines via 1,3-Dipolar Cycloaddition Reactions of Azomethine Ylides. Molecules 2015, 20, 780-791.

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