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- Title
Reductive Cyclization of Bromoenynamides with Alcohols as Hydride Source: Synthesis and Reactions of 2-Amidodienes.
- Authors
Greenaway, Rebecca L.; Campbell, Craig D.; Chapman, Helen A.; Anderson, Edward A.
- Abstract
Under basic conditions in alcoholic solvents, bromoenynamides undergo palladium-catalyzed cyclization to cyclic 2-amidodienes in good to excellent yields. This process represents the first use of an alcohol as a hydride source in an alkyne carbopalladation/termination sequence, with the site selectivity of the reduction showing a strong dependence on the tethering ring size (5-8), and the nature of the alcohol and base. Reaction of the dienes with a range of dienophiles (including alkenes, alkynes and arynes) under various conditions gives bi- and tricyclic azacycles, which can be further oxidized to the aromatic azacycles.
- Publication
Advanced Synthesis & Catalysis, 2012, Vol 354, Issue 17, p3187
- ISSN
1615-4150
- Publication type
Article
- DOI
10.1002/adsc.201200703