New approaches to bicylic vinyl heterocycles from propargylic acetals

Le Strat, Frédéric, Harrowven, David C. and Maddaluno, Jacques (2005) New approaches to bicylic vinyl heterocycles from propargylic acetals. Journal of Organic Chemistry, 70 (2), 489-498. (doi:10.1021/jo048794d).

Record type: Article

Abstract

The paper describes further studies on the intramolecular carbolithiation of propargylic acetals with aryllithiums leading to 2-vinylbenzofurans and 3-vinylfuropyridines. Attempts to extend the cascade to [4.4.0] binuclear heterocycles met with limited success. An alternative, two-step entry, to such ring systems has been developed using the palladium-induced cyclization/hydride capture methodology. A new route to isoquinilinones from simple benzamides is also disclosed.

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Submitted date: 15 July 2004

Published date: 21 January 2005

Keywords: diels-alder reactions, catalyzed tandem cyclization, anion capture processes, carbazole derivatives, annellated indoles, 3-vinylindoles, access, carbodienophiles, -cycloadditions, 3-vinylbenzofurans

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