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Synthesis of Aryl-Substituted 1,4-Dihydroquinolines by [4+2] Cycloaddition of Benzyne with 1-Azadienes

Abstract The synthesis of aryl-substituted 1,4-dihydroquinolines can be achieved using a [4+2] cycloaddition between benzyne and various aryl-substituted 1-azadienes. The conditions are tolerated by N-aryl-, alkyl-, tosyl-, and TERT-butoxycarbonyl-protected 1-azadienes. A short synthesis of the fung...

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Bibliographic Details
Published in:Synlett 2012-02, Vol.2012 (3), p.389-392
Main Authors: Stokes, Sean, Bekkam, Markondaiah, Rupp, Madeline, Mead, Keith T.
Format: Article
Language:English
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Summary:Abstract The synthesis of aryl-substituted 1,4-dihydroquinolines can be achieved using a [4+2] cycloaddition between benzyne and various aryl-substituted 1-azadienes. The conditions are tolerated by N-aryl-, alkyl-, tosyl-, and TERT-butoxycarbonyl-protected 1-azadienes. A short synthesis of the fungal metabolite 3-O-methylviri­dicatin is reported.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0031-1290137