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Synthesis 2012; 44(9): 1410-1416
DOI: 10.1055/s-0031-1290504
DOI: 10.1055/s-0031-1290504
paper
A Concise Synthesis of 3-Arylated Di- and Tetrahydro-2H-2-benzazepin-1-ones; A New Synthetic Approach to the Homoprotoberberine Framework
Further Information
Publication History
Received: 13 December 2011
Accepted after revision: 14 February 2012
Publication Date:
16 March 2012 (online)
Abstract
A variety of 3-arylated di- and tetrahydro-2H-2-benzazepin-1-ones were efficiently assembled through a sequence involving a Suzuki–Miyaura cross-coupling reaction with enol phosphates derived from the corresponding benzazepine-1,3-diones. This technique has been further exploited for the construction of the homoprotoberberine skeleton, which was readily accessed by intramolecular carbocationic annulation reaction applied to a suitably substituted precursor.
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