Palladium-Catalyzed Synthesis of 1,2,3,4-Tetrahydro-5H-2-benzazepin-5-ones

Kazumi Okuro; Howard Alper

doi:10.1055/s-0032-1317183

Synlett, Table of Contents

Synlett 2012; 23(17): 2531-2533
DOI: 10.1055/s-0032-1317183

letter

Palladium-Catalyzed Synthesis of 1,2,3,4-Tetrahydro-5H-2-benzazepin-5-ones

Authors

Kazumi Okuro

Centre for Catalysis Research and Innovation, Department of Chemistry, University of Ottawa, 10 Marie Curie, Ottawa, Ontario, K1N 6N5, Canada, Fax: +1(613)5625871 Email: howard.alper@uottawa.ca
Howard Alper*

Centre for Catalysis Research and Innovation, Department of Chemistry, University of Ottawa, 10 Marie Curie, Ottawa, Ontario, K1N 6N5, Canada, Fax: +1(613)5625871 Email: howard.alper@uottawa.ca

Abstract

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Abstract

Palladium-catalyzed intermolecular cyclocarbonylation of 2-iodobenzylamines with Michael acceptors produces 1,2,3,4-tetrahydro-5H-2-benzazepin-5-one derivatives in moderate to good yields. This methodology enables the direct preparation of highly functionalized 1,2,3,4-tetrahydro-5H-2-benzazepin-5-ones from readily available starting materials.

Key words

cyclocarbonylation - heterocycles - palladium - 1,2,3,4-tetrahydrobenzazepin-5-one - Michael acceptor

Full Text

References

References
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6 General Procedure: A mixture of 1 (1.0 mmol), Michael acceptor 2 (1.2 mmol or 2.0 mmol), Pd₂(dba)₃⋅CHCl₃ (0.025 mmol, 25.9 mg), PCy₃HBF₄ (0.1 mmol, 36.8 mg), and Et₃N (10 mmol, 1.01 g) in MeCN (2 mL) was charged in a glass liner, equipped with a magnetic stirring bar. The glass liner was then inserted into a 45-mL autoclave. The autoclave was flushed with CO (5 ×) and pressurized to 100 psi. The autoclave was heated at 80 °C with stirring. After the reaction, the autoclave was cooled to r.t. prior to the release of CO. The solvent was evaporated under reduced pressure, and the product was purified by silica gel column chroma-tography with n-hexane and Et₂O as the eluent.
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Supplementary Material

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