One-pot Claisen rearrangement/O-methylation/alkene isomerization in the synthesis of ortho-methoxylated phenylisopropylamines

Tetrahedron Letters

Volumn 37, Issue 44, 1996, Pages 7889-7892

  Waldman, Steve R ^a   Monte, Aaron P ^b   Bracey, Ann ^a   Nichols, David E ^a  

^a PURDUE UNIVERSITY   (United States)

^b UNIVERSITY OF WISCONSIN LA CROSSE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; BENZOFURAN DERIVATIVE; PHENYLISOPROPYLAMINE DERIVATIVE; SEROTONIN AGONIST; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 16044369706     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01807-2     Document Type: Article

References (13)

1. 1. Nichols, D. E.; Snyder, S. E.; Oberlender, R.; Johnson, M. P.; Huang, X. J. Med. Chem. 1991, 34, 276-281.
2. 2. Titeler, M.; Lyon R. A.,; Glennon, R. A. Psychopharmacology 1988, 94, 213-216; Sanders-Bush, E.; Burris, K. D.; Knoth, K. J. Pharmacol. Exp. Ther. 1988, 246, 924-928; Seggal, M. R., Yousif, M. Y.; Lyon, R. A.; Titeler, M.; Roth, B. L.; Suba, E. A.; Glennon, R. A. J. Med. Chem. 1990, 33, 1032-1036; Glennon, R. A.; Raghupathi, R.; Bartyzel, P.; Teitler, M.; Leonhardt, S. J. Med. Chem. 1992, 35, 734-740.
3. 2. Titeler, M.; Lyon R. A.,; Glennon, R. A. Psychopharmacology 1988, 94, 213-216; Sanders-Bush, E.; Burris, K. D.; Knoth, K. J. Pharmacol. Exp. Ther. 1988, 246, 924-928; Seggal, M. R., Yousif, M. Y.; Lyon, R. A.; Titeler, M.; Roth, B. L.; Suba, E. A.; Glennon, R. A. J. Med. Chem. 1990, 33, 1032-1036; Glennon, R. A.; Raghupathi, R.; Bartyzel, P.; Teitler, M.; Leonhardt, S. J. Med. Chem. 1992, 35, 734-740.
4. 2. Titeler, M.; Lyon R. A.,; Glennon, R. A. Psychopharmacology 1988, 94, 213-216; Sanders-Bush, E.; Burris, K. D.; Knoth, K. J. Pharmacol. Exp. Ther. 1988, 246, 924-928; Seggal, M. R., Yousif, M. Y.; Lyon, R. A.; Titeler, M.; Roth, B. L.; Suba, E. A.; Glennon, R. A. J. Med. Chem. 1990, 33, 1032-1036; Glennon, R. A.; Raghupathi, R.; Bartyzel, P.; Teitler, M.; Leonhardt, S. J. Med. Chem. 1992, 35, 734-740.
5. 2. Titeler, M.; Lyon R. A.,; Glennon, R. A. Psychopharmacology 1988, 94, 213-216; Sanders-Bush, E.; Burris, K. D.; Knoth, K. J. Pharmacol. Exp. Ther. 1988, 246, 924-928; Seggal, M. R., Yousif, M. Y.; Lyon, R. A.; Titeler, M.; Roth, B. L.; Suba, E. A.; Glennon, R. A. J. Med. Chem. 1990, 33, 1032-1036; Glennon, R. A.; Raghupathi, R.; Bartyzel, P.; Teitler, M.; Leonhardt, S. J. Med. Chem. 1992, 35, 734-740.
6. 3. See, for example Murray, R. D. H., and Ballantyne, M. M. Tetrahedron 1970, 26, 4667-4671.
7. 4. Pelletier, J. D. and Poirer, D. Tetrahedron Lett., 1994, 35, 1051-1054.
8. 5 Monte, A. P. Structure-Activity Relationships of Hallucinogens: Design, Synthesis, and Pharmacological Evaluation of a Series of Conformationally Restricted Phenethylamines, Ph.D. thesis, 214 pp, Purdue University, 1995.
9. 6. Sy, W. and By, A. W. Tetrahedron Lett. 1985, 26, 1193-1196.
10. 7. Sy, W. Tetrahedron Lett. 1993, 34, 6223-6224.
11. 8. Monte, A. P.; Marona-Lewicka, D.; Parker, M. A.; Wainscott, D. B.; Nelson, D. L.; Nichols, D. E. J. Med. Chem. 1996, in press; A. Monte, et al., manuscripts in preparation.
12. 2Br), 6.6 (s, 1, ArH), 6.9 (s, 1, ArH).
13. 3, J = 16 Hz), 6.8 (s, 1, ArH).