Synlett 2012; 23(17): 2531-2533
DOI: 10.1055/s-0032-1317183
letter
© Georg Thieme Verlag Stuttgart · New York

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

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
› Author Affiliations
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.

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
    • 9a Kobayashi T, Tanaka M. Tetrahedron Lett. 1986; 27: 4745
    • 9b Negishi E, Zhang Y, Shimoyama I, We G. J. Am. Chem. Soc. 1989; 111: 8018