Synthesis 2015; 47(18): 2721-2730
DOI: 10.1055/s-0034-1379931
special topic
© Georg Thieme Verlag Stuttgart · New York

Dipolar Cycloaddition-Based Multicomponent Reactions in Ionic Liquids: A Green, Fully Stereoselective Synthesis of Novel Polycyclic Cage Systems with the Generation of Two New Azaheterocyclic Rings

Raju Suresh Kumar*
a  Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Kingdom of Saudi Arabia   Email: sraju@ksu.edu.sa
,
Abdulrahman I. Almansour
a  Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Kingdom of Saudi Arabia   Email: sraju@ksu.edu.sa
,
Natarajan Arumugam
a  Department of Chemistry, College of Science, King Saud University, P.O. Box 2455, Riyadh 11451, Kingdom of Saudi Arabia   Email: sraju@ksu.edu.sa
,
J. Carlos Menéndez*
b  Departamento de Química Orgánica y Farmacéutica, Facultad de Farmacia, Universidad Complutense, 28040 Madrid, Spain
,
Hasnah Osman
c  School of Chemical Sciences, Universiti Sains Malaysia, Minden 11800, Penang, Malaysia
,
Raju Ranjith Kumar
d  Department of Organic Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai 625021, India
› Author Affiliations
Further Information

Publication History

Received: 09 April 2015

Accepted after revision: 06 May 2015

Publication Date:
09 July 2015 (eFirst)

Abstract

Two libraries of novel, bifunctional polycyclic cage structures have been synthesized for the first time in an ionic liquid, 1-butyl-3-methylimidazolium bromide ([bmim]Br), employing a sustainable microwave-assisted, one-pot, three-component [3+2] cycloaddition–annulation protocol in good to excellent yields. The ring systems thus generated contain as structural elements bridged, fused and spiro rings and were obtained with complete regio- and stereoselectivity through the creation of two C–C and two C–N bonds, which led to the generation of two azaheterocyclic rings and five adjacent stereogenic carbons, three of which are quaternary.

Supporting Information

 
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