Article ID | Journal | Published Year | Pages | File Type |
---|---|---|---|---|
5217375 | Tetrahedron | 2013 | 9 Pages |
Abstract
A variety of difficult to obtain benzo[c]azepine-1-ones are synthesized via a novel palladium-catalyzed, silver-promoted intramolecular cyclization of cyclopropyl benzamides. This biologically important class of molecules is prepared in an efficient and high-yielding manner from easily accessible starting materials. Both aryl bromides and iodides are effective substrates for the transformation. Mechanistic studies indicate that the reaction proceeds through a cyclopropyl C(sp3)-H cleavage step, followed by ring-opening, deprotonation, and reductive elimination.
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Related Topics
Physical Sciences and Engineering
Chemistry
Organic Chemistry
Authors
Carolyn L. Ladd, Daniela Sustac Roman, André B. Charette,