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New approaches to bicylic vinyl heterocycles from propargylic acetals

New approaches to bicylic vinyl heterocycles from propargylic acetals
New approaches to bicylic vinyl heterocycles from propargylic acetals
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.
diels-alder reactions, catalyzed tandem cyclization, anion capture processes, carbazole derivatives, annellated indoles, 3-vinylindoles, access, carbodienophiles, -cycloadditions, 3-vinylbenzofurans
0022-3263
489-498
Le Strat, Frédéric
5d1cb200-f6fb-4735-a6f7-df4fa4ca8119
Harrowven, David C.
aae936c3-fdf8-4e87-ac7b-48f8b7fd1bff
Maddaluno, Jacques
37e0bd01-a822-42e2-832d-69dc876fcefa
Le Strat, Frédéric
5d1cb200-f6fb-4735-a6f7-df4fa4ca8119
Harrowven, David C.
aae936c3-fdf8-4e87-ac7b-48f8b7fd1bff
Maddaluno, Jacques
37e0bd01-a822-42e2-832d-69dc876fcefa

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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More information

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

Identifiers

Local EPrints ID: 20843
URI: http://eprints.soton.ac.uk/id/eprint/20843
ISSN: 0022-3263
PURE UUID: fdfffa1e-5848-4ef8-93d2-0926558ec577

Catalogue record

Date deposited: 02 Mar 2006
Last modified: 15 Jul 2019 19:25

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