Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000083.xml
Synlett 2012; 23(17): 2531-2533
DOI: 10.1055/s-0032-1317183
DOI: 10.1055/s-0032-1317183
letter
Palladium-Catalyzed Synthesis of 1,2,3,4-Tetrahydro-5H-2-benzazepin-5-ones
Further Information
Publication History
Received: 13 June 2012
Accepted after revision: 09 August 2012
Publication Date:
28 September 2012 (online)
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 acceptorSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synlett.
- Supporting Information
-
References
- 1 Mitani N, Inagaki J, Kuwabara R, Sato M PCT Int. Appl. WO037128, 2011; Chem. Abstr. 2011; 154: 409839
- 2 Toda N, Tago K, Marumoto S, Takami K, Ori M, Yamada N, Koyama K, Naruto S, Abe K, Yamazaki R, Hara T, Aoyagi A, Abe Y, Kaneko T, Kogen H. Bioorg. Med. Chem. 2003; 11: 4389
- 3a Liu S, Yang Y.-LA, Sambandam A, Molino BF, Olson RE PCT Int. Appl. WO141082, 2008; Chem. Abstr. 2008; 149: 576408
- 3b Molino B. F., Liu S., Sambandam A., Guzzo P. R., Hu M., Zha C., Nacro K., Manning D. D., Isherwood M. L., Fleming K. N., Chu W., Olson R. E.; PCT Int. Appl. WO011820, 2007; Chem. Abstr. 2007, 146, 184383.
- 4a McLean A, Proctor GR. J. Chem. Soc., Perkin Trans. 1 1972; 1084
- 4b Macdonald I, Proctor GR. J. Chem. Soc. C 1970; 1461
- 4c Bachand C., Belema M., Deon D. H., Good A. C., Goodrich J., James C. A., Lavoie R., Lopez O. D., Martel A., Meanwell N. A., Nguyen V. N., Romine J. L., Ruediger E. H., Snyder L. B., St. Laurent D. R., Yang F., Langley D. R., Wang G., Hamann L. G.; US Patent 0202478, 2009; Chem. Abstr. 2009, 151, 267309.
- 5 Okuro K, Alper H. J. Org. Chem. 2012; 77: 4420
- 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.
- 7 Netherton MR, Fu GC. Org. Lett. 2001; 3: 4295
- 8 Tsuji J. Palladium Reagents and Catalysts . Wiley & Sons; Hoboken: 1995