New approach to 4-phenyl-β-aminotetralin from 4-(3-halophenyl)tetralen-2-ol phenylacetate

Tetrahedron Letters

Volumn 50, Issue 36, 2009, Pages 5107-5109

  Vincek, Adam S ^a   Booth, Raymond G ^a  

^a UNIVERSITY OF FLORIDA HEALTH   (United States)

Author keywords

Aminotetralin; Cascade; Halostryene; Phenylacetate; Tetralen 2 ol

Indexed keywords

4 (3 HALOPHENYL)TETRALEN 2 OL PHENYLACETATE; 4 PHENYL BETA AMINOTETRALIN; 4 PHENYLTETRALEN 2 OL PHENYLACETATE; BENZENE DERIVATIVE; BROMINE DERIVATIVE; BROMOPHENYLTETRALEN 2 OL PHENYLACETATE; CHLORINE DERIVATIVE; CYCLOALKANE DERIVATIVE; FLUORINE DERIVATIVE; PHENYLACETIC ACID DERIVATIVE; TETRALIN DERIVATIVE; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ACYLATION; ALCOHOLYSIS; ALKYLATION; ARTICLE; CYCLIZATION; FRIEDEL CRAFTS REACTION; HYDROGENATION; QUANTUM YIELD; REACTION ANALYSIS; SUZUKI REACTION;

EID: 67650499136     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.06.099     Document Type: Article

References (42)

1. Rowland N.E., Crump E.M., Nguyen N., Robertson K., Sun Z., and Booth R.G. Pharmacol., Biochem. Behav. 91 (2008) 176
2. Ghoneim O.M., Legere J.A., Golbraikh A., Tropsha A., and Booth R.G. Bioorg. Med. Chem. 14 (2006) 6640
3. Bucholtz E.C., Brown R.L., Tropsha A., Booth R.G., and Wyrick S.D. J. Med. Chem. 42 (1999) 3041
4. Youngman M.A., Willard N.M., Dax S.L., and McNally J.J. Synth. Commun. 33 (2003) 2215
5. 2 GPCRs for will be reported in J. Med. Chem.
6. Schreiber S.L. Nature 457 (2009) 153
7. Ahn Y., Ko S.-B., Kim M.-J., and Park J. Coord. Chem. Rev. 252 (2008) 647
8. Panella L., Feringa B.L., de Vries J.G., and Minnaard A. J. Org. Lett. 7 (2005) 4177
9. In: Tsuji J. (Ed). Palladium in Organic Synthesis. Topics in Organometallic Chemistry Vol. 14 (2005), Springer, Berlin
10. Nakagawa H., Okimoto Y., Sakaguchi S., and Ishii Y. Tetrahedron Lett. 44 (2003) 103
11. In: Miyaura N. (Ed). Cross-Coupling Reactions. Topics in Current Chemistry Vol. 219 (2002), Springer, Berlin
12. Carreño M.C., González-López M., Latorre A., and Urbano A. J. Org. Chem. 71 (2006) 4956
13. Silveira C.C., Machado A., Braga A.L., and Lenardão E.J. Tetrahedron Lett. 45 (2004) 4077
14. Silveira C.C., Braga A.L., Kaufman T.S., and Lenardão E.J. Tetrahedron 60 (2004) 8295
15. Lutz R.E., Bailey P.S., and Shearer Jr. N.H. J. Am. Chem. Soc. 68 (1946) 2224
16. Fine S.A., and Stern R.L. J. Org. Chem. 32 (1967) 4132
17. Fine S.A., and Stern R.L. J. Org. Chem. 35 (1970) 1857
18. Rhee S.W., and Tanga M.J. J. Labelled Compd. Radiopharm. 43 (2000) 925
19. Wyrick S.D., Booth R.G., Myers A.M., Owens C.E., Kula N.S., Baldessarini R.J., McPhail A.T., and Mailman R.B. J. Med. Chem. 36 (1993) 2542
20. Khalaf A.A., and El-Khawaga A.M.A. Rev. Roum. Chim. 26 (1981) 739
21. Bertolini G., Vecchietti V., Mabilia M., Norcini G., Restelli A., Santangelo F., Villa A.M., and Casagrande C. Eur. J. Med. Chem. 27 (1992) 663
22. Gatti G., Piersanti G., and Spadoni G. Farmaco 58 (2003) 469
23. Prakash S.G.K., Yan P., Török B., and Olah G.A. Catal. Lett. 87 (2003) 109
24. Brook M.A., Henry C., Jefferson E., Jüschke R., Sebastian T., Tomaszewski M., and Wenzel S. Bull. Soc. Chim. Fr. 132 (1995) 559
25. Fleming I., and Pearce A. J. Chem. Soc., Perkin Trans. 1 11 (1980) 2485
26. Lucarini S., Bedini A., Spadoni G., and Piersanti G. Org. Biomol. Chem. 6 (2008) 147
27. Galli C. Synthesis 4 (1979) 303
28. Gray A.D., and Smyth T.P. J. Org. Chem. 66 (2001) 7113
29. Smith S.M., Reyes S.M., Bravo O.V., Herrera M.A.F., Pascual R.M., Ramírez J.S., Fuente A., Reyes M., and Ruiz J.A. ARKIVOC 6 (2005) 127
30. Veeramaneni V.R., Pal M., and Yeleswarapu K.R. Tetrahedron 59 (2003) 3283
31. Nevy J.B., Hawkinson D.C., Blotny G., Yao X., and Pollack R.M. J. Am. Chem. Soc. 119 (1997) 12722
32. Yao X., Gold M.A., and Pollack R.M. J. Am. Chem. Soc. 121 (1999) 6220
33. Matyjaszewski K., and Sawamoto M. In: Matyjaszewski K. (Ed). Cationic Polymerizations Mechanism, Synthesis, and Applications (1996), Marcel Dekker, New York 323
34. Wang X.-Z., Yao Z.-J., Liu H., Zhang M., Yang D., George C., and Burke Jr. T.R. Tetrahedron 59 (2003) 6087
35. Peach P., Cross D.J., Kenny J.A., Mann I., Houson I., Campbell L., Walsgrove T., and Wills M. Tetrahedron 62 (2006) 1864
36. Mogi M., Fuji K., and Node M. Tetrahedron: Asymmetry 15 (2004) 3715
37. Alcock N.J., Mann I., Peach P., and Wills M. Tetrahedron: Asymmetry 13 (2002) 2485
38. Bosse K., Marineau J., Nason D.M., Fliri A.J., Segelstein B.E., Desai K., and Volkmann R.A. Tetrahedron Lett. 47 (2006) 7285
39. Lamberts J.J.M., Cuppen T.J.H.M., and Laarhoven W.H. J. Chem. Soc., Perkin Trans. 1 9 (1985) 1819
40. Monguchi Y., Kume A., Hattori K., Maegawa T., and Sajiki H. Tetrahedron 62 (2006) 7926
41. Wolfe J.P., Singer R.A., Yang B.H., and Buchwald S.L. J. Am. Chem. Soc. 121 (1999) 9550
42. Wolfe J.P., and Buchwald S.L. Angew. Chem., Int. Ed. 38 (1999) 2413