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

Natarajan Arumugam; Abdulrahman I Almansour; Raju Suresh Kumar; J Carlos Menéndez; Mujeeb A Sultan; Usama Karama; Hazem A Ghabbour; Hoong-Kun Fun

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

Molecules. 2015 Sep 3;20(9):16142-53. doi: 10.3390/molecules200916142.

Authors

Natarajan Arumugam¹, Abdulrahman I Almansour², Raju Suresh Kumar³, J Carlos Menéndez⁴, Mujeeb A Sultan⁵, Usama Karama⁶, Hazem A Ghabbour⁷, Hoong-Kun Fun^{8

9}

Affiliations

¹ Department of Chemistry, College of Science, King Saud University, P. O. Box 2455, Riyadh 11451, Saudi Arabia. anatarajan@ksu.edu.sa.
² Department of Chemistry, College of Science, King Saud University, P. O. Box 2455, Riyadh 11451, Saudi Arabia. almansor@ksu.edu.sa.
³ Department of Chemistry, College of Science, King Saud University, P. O. Box 2455, Riyadh 11451, Saudi Arabia. sraju@ksu.edu.sa.
⁴ Departamento de Química Orgánica y Farmacéutica, Facultad de Farmacia, Universidad Complutense, Madrid 28040, Spain. josecm@farm.ucm.es.
⁵ Department of Chemistry, College of Science, King Saud University, P. O. Box 2455, Riyadh 11451, Saudi Arabia. alhosami1983@yahoo.co.uk.
⁶ Department of Chemistry, College of Science, King Saud University, P. O. Box 2455, Riyadh 11451, Saudi Arabia. karama@ksu.edu.sa.
⁷ Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi Arabia. ghabbourh@yahoo.com.
⁸ Department of Pharmaceutical Chemistry, College of Pharmacy, King Saud University, P.O. Box 2457, Riyadh 11451, Saudi Arabia. hfun.c@ksu.edu.sa.
⁹ Ray Crystallography Unit, School of Physics, Universiti Sains Malaysia, Penang 11800, Malaysia. hfun.c@ksu.edu.sa.

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.

Keywords: 1,3-dipolar cycloaddition reactions; ionic liquids; multicomponent reactions; spirooxindoles; spiropyrrolidines.

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Anthracenes / chemical synthesis*
Anthracenes / chemistry
Cycloaddition Reaction
Humans
Indoles / chemical synthesis*
Indoles / chemistry
Models, Molecular
Molecular Structure

Substances

Anthracenes
Indoles