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Molecules 2015, 20(9), 16142-16153; doi:10.3390/molecules200916142

An Expedient Regio- and Diastereoselective Synthesis of Hybrid Frameworks with Embedded Spiro[9,10]dihydroanthracene [9,3′]-pyrrolidine and Spiro[oxindole-3,2′-pyrrolidine] Motifs via an Ionic Liquid-Mediated Multicomponent Reaction

1
Department of Chemistry, College of Science, King Saud University, P. O. Box 2455, Riyadh 11451, Saudi Arabia
2
Departamento de Química Orgánica y Farmacéutica, Facultad de Farmacia, Universidad Complutense, Madrid 28040, Spain
3
Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi Arabia
4
Ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, Penang 11800, Malaysia
*
Authors to whom correspondence should be addressed.
Academic Editor: Romano V. A. Orru
Received: 8 August 2015 / Revised: 21 August 2015 / Accepted: 24 August 2015 / Published: 3 September 2015
(This article belongs to the Special Issue MCRs and Related One-Pot Organic Synthesis)
View Full-Text   |   Download PDF [908 KB, uploaded 3 September 2015]   |  

Abstract

A series of hitherto unreported anthracene-embedded dispirooxindoles has been synthesized via a one-pot three-component 1,3-dipolar cycloaddition reaction of an azomethine ylide, generated in situ from the reaction of isatin and sarcosine to 10-benzylideneanthracen-9(10H)-one as a dipolarophile in 1-butyl-3-methylimidazolium bromide([bmim]Br), an ionic liquid. This reaction proceeded regio- and diastereoselectively, in good to excellent yields. View Full-Text
Keywords: multicomponent reactions; 1,3-dipolar cycloaddition reactions; spirooxindoles; spiropyrrolidines; ionic liquids multicomponent reactions; 1,3-dipolar cycloaddition reactions; spirooxindoles; spiropyrrolidines; 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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MDPI and ACS Style

Arumugam, N.; Almansour, A.I.; Kumar, R.S.; Menéndez, J.C.; Sultan, M.A.; Karama, U.; Ghabbour, H.A.; Fun, H.-K. An Expedient Regio- and Diastereoselective Synthesis of Hybrid Frameworks with Embedded Spiro[9,10]dihydroanthracene [9,3′]-pyrrolidine and Spiro[oxindole-3,2′-pyrrolidine] Motifs via an Ionic Liquid-Mediated Multicomponent Reaction. Molecules 2015, 20, 16142-16153.

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