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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

1
Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Saudi Arabia
2
Centro de Química-Física Molecular and Institute of Nanoscience and Nanotechnology, Instituto Superior Técnico, Universidade de Lisboa, Lisboa 1049-001, Portugal
3
Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi Arabia
4
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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Abstract

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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MDPI and ACS Style

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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