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; Abdulrahman I. Almansour; Natarajan Arumugam; J. Carlos Menéndez; Hasnah Osman; Raju Ranjith Kumar

doi:10.1055/s-0034-1379931

Synthesis, Inhaltsverzeichnis

Synthesis 2015; 47(18): 2721-2730
DOI: 10.1055/s-0034-1379931

special topic

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*

^aDepartment 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

^aDepartment 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

^aDepartment 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*

^bDepartamento de Química Orgánica y Farmacéutica, Facultad de Farmacia, Universidad Complutense, 28040 Madrid, Spain

,

Hasnah Osman

^cSchool of Chemical Sciences, Universiti Sains Malaysia, Minden 11800, Penang, Malaysia

,

Raju Ranjith Kumar

^dDepartment of Organic Chemistry, School of Chemistry, Madurai Kamaraj University, Madurai 625021, India

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Abstract

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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.

Key words

azomethine ylides - [3+2] cycloadditions - ionic liquids - stereoselective synthesis - spiro compounds

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Referenzen

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