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Synlett 2012(3): 389-392  
DOI: 10.1055/s-0031-1290137
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

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

Sean Stokes, Markondaiah Bekkam, Madeline Rupp, Keith T. Mead*
Department of Chemistry, Mississippi State University, MS State, Mississippi 39762, USA
Fax: +1(662)3251618; e-Mail: kmead@chemistry.msstate.edu;
Further Information

Publication History

Received 25 October 2011
Publication Date:
19 January 2012 (online)

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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.

Key words

benzyne - dihydroquinolines - azadienes - cycloaddition - 3-O-methylviridicatin

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