Formation of 4-N-arylamino-1-butanol derivatives from aromatic nitro compounds via a novel palladium-catalyzed tetrahydrofuran ring-opening reaction

Synthetic Communications

Volumn 42, Issue 23, 2012, Pages 3413-3418

  Moran, Brian W ^a   Kenny, Peter T M ^a  

^a DUBLIN CITY UNIVERSITY   (Ireland)

Author keywords

4 Amino 1 butanol; nitro; palladium catalyzed; reduction; ring opening; siloxane; tetrahydrofuran

Indexed keywords

4 ARYLAMINO 1 BUTANOL DERIVATIVE; AROMATIC NITRO COMPOUND; BUTANOL; HYDROGEN PEROXIDE; PALLADIUM; POTASSIUM FLUORIDE; TETRAHYDROFURAN; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL REACTION; SYNTHESIS;

EID: 84864658053     PISSN: 00397911     EISSN: 15322432     Source Type: Journal    
DOI: 10.1080/00397911.2011.582978     Document Type: Article

References (14)

1. Yuan, D.; Brown, R. G.; Hepworth, J. D.; Alexiou, M. S.; Tyman, J. H. P. J. Heterocyclic Chem. 2008, 45, 397.
2. D'Andrea, S.; Zheng, Z. B.; DenBleyker, K.; Fung-Tomc, J. C.; Yang, H.; Clark, J.; Taylor, D.; Bronson, J. Bioorg. Med. Chem. Lett. 2005, 15, 2834.
3. Flaniken, J. M.; Collins, J. C.; Lanz, M.; Singaram, B. Org. Lett. 1999, 1, 799.
4. Shafir, A.; Lichtor, P. A.; Buchwald, S. L. J. Am. Chem. Soc. 2007, 129, 3490.
5. Russell, H. F.; Bremner, J. B.; Bushelle-Edghill, J.; Lewis, M. R.; Thomas, S. R.; Bates II, F. Tetrahedron Lett. 2007, 48, 1637.
6. Moran, B. W.; Anderson, F. P.; Devery, A.; Cloonan, S.; Butler, W. E.; Varughese, S.; Draper, S. M.; Kenny, P. T. M. Bioorg. Med. Chem. 2009, 17, 4510.
7. Rahaim, R. J.; Maleczka, R. E. Synthesis 2006, 19, 3316.
8. Wichterle, O. Collect. Czech. Chem. Commun. 1949, 14, 209.
9. Winberg, H. E. U.S. Patent 2,628,978, 1953.
10. McCalmont, W. F.; Patterson, J. R.; Lindenmuth, M. A.; Heady, T. N.; Haverstick, D. M.; Gray, L. S.; Macdonald, T. L. Bioorg. Med. Chem. 2005, 13, 3821.
11. Boisson, C.; Berthet, J. C.; Lance, M.; Nierlich, M.; Ephritikhine, M. Chem. Commun. 1996, 18, 2129.
12. Borkowsky, S. L.; Jordan, R. F.; Hinch, G. D. Organometallics 1991, 10, 1268.
13. Lunsford, C. D.; Murphey, R. S.; Rose, E. K. J. Org. Chem. 1957, 22, 1225.
14. Behforouz, M.; Cai, W.; Mohammadi, F.; Stocksdale, M. G.; Gu, Z.; Ahmadian, M.; Baty, D. E.; Etling, M. R.; Al-Anzi, C. H.; Swiftney, T. M.; Tanzer, L. R.; Merriman, R. L.; Behforouz, N. C. Bioorg. Med. Chem. 2007, 15, 495.