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Synthesis 2015; 47(18): 2721-2730
DOI: 10.1055/s-0034-1379931
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
Further Information
Publication History
Received: 09 April 2015
Accepted after revision: 06 May 2015
Publication Date:
09 July 2015 (online)
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 compoundsSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0034-1379931.
- Supporting Information
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For a review of the concept of multiple bond-forming transformations, see:
For a special issue on the use of multiple bond-forming reactions in the synthesis of heterocycles, see:
Representative examples: For antitumour activity, see:
For nociceptin agonism, see:
For nociceptin antagonism, see: