Synthesis of 5-substituted 7,8-benzomorphans by intramolecular cyclization of N-protected 4,4-disubstituted 1,4-dihydropyridines

Synthesis

Volumn , Issue 13, 2010, Pages 2147-2160

  Schmaunz, Cornelia E ^a   Pabel, Jörg ^a   Wanner, Klaus T ^a  

^a UNIVERSITY OF MUNICH   (Germany)

Author keywords

alkaloids; benzomorphans; electrophilic aromatic substitution; intramolecular cyclization; N acyliminium ion

Indexed keywords

ACYLIMINIUM ION; CYCLIZATION REACTIONS; DIHYDROPYRIDINES; ELECTROPHILIC AROMATIC SUBSTITUTIONS; INTRAMOLECULAR CYCLIZATIONS; RING SYSTEMS;

AROMATIC COMPOUNDS; AROMATIZATION; IONS; PYRIDINE; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

CYCLIZATION;

1,4 DIHYDROPYRIDINE DERIVATIVE; 2' HYDROXY 2,9 DIMETHYL 5 PHENYL 6,7 BENZOMORPHAN; 7,8 BENZOMORPHAN; 7,8 BENZOMORPHAN DERIVATIVE; ANALGESIC AGENT; BENZOMORPHAN; BENZOMORPHAN DERIVATIVE; DIORGANOMAGNESIUM DERIVATIVE; MAGNESIUM DERIVATIVE; MORPHAN; MORPHINE; MORPHINE DERIVATIVE; N SILYLPYRIDINIUM; NATURAL PRODUCT; PYRIDINIUM DERIVATIVE; UNCLASSIFIED DRUG;

ANALGESIC ACTIVITY; ARTICLE; CYCLIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; ELECTROPHILICITY; STRUCTURE ACTIVITY RELATION; SUBSTITUTION REACTION;

EID: 77953845025     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0029-1218808     Document Type: Article

References (25)

1. Bosch J, Bonjoch J, Heterocycles 1980 14 505
2. Frackenpohl J, Chem. Unserer Zeit 2000 34 99
3. Palmer D C., Strauss M J., Chem. Rev. 1977 77 1
4. Carroll F I., Melvin M S., Nuckols M C., Mascarella S W., Navarro H A., Thomas J B., J. Med. Chem. 2006 49 1781
5. Kim I J., Dersch C M., Rothmann R B., Jacobson A E., Rice K C., Bioorg. Med. Chem. 2004 12 4543
6. Thomas J B., Zhang L, Navarri H A., Carroll F I., J. Med. Chem. 2006 49 5597
7. Latshaw W E., MacDonnell D R., J. Pharm. Sci. 1961 50 792
8. Englberger W, Sattlegger M, Przewosny M, WO 9,965,485 1999
9. Yokoyama N, Almaula P I., Block F B., Granat F R., Gottfried N, Hill R T., McMahon E H., Munch W F., Rachlin H, Saelens J K., Siegel M G., Tomaselli H C., Clarke F H., J. Med. Chem. 1979 22 537
10. Bosch J, Canals J, Granados R, J. Heterocycl. Chem. 1975 12 1117
11. Khartulyari A S., Maier M E., Eur. J. Org. Chem. 2007 317
12. Magnus P, Fairhurst R A., J. Chem. Soc., Chem. Commun. 1994 1541
13. Bosch J, Bonjoch J, Diez A, Linares A, Moral M, Rubiralta M, Tetrahedron 1985 41 1753
14. Klegraf E, Knauer S, Kunz H, Angew. Chem. Int. Ed. 2006 45 2623
15. Kometani T, Shiotani S, J. Med. Chem. 1978 21 1105
16. Bräckow J, Wanner K T., Tetrahedron 2006 62 2395
17. Bräckow J, Ph.D. Thesis LMU München Germany 2006
18. Reichardt C, Solvents and Solvent Effects in Organic Chemistry Vol. 3 VCH Weinheim 2003
19. Perrin D D., Armarego W L. F., In Purification of Laboratory Chemicals Vol. 3 Pergamon New York 1988
20. Shiao M.-J, Chia W.-L, Synth. Commun. 1991 21 401
21. Wakefield B J., Organomagnesium Methods in Organic Synthesis Academic New York 1995 65-67
22. Akiba K.-Y, Iseki Y, Wada M, Tetrahedron Lett. 1982 23 3935
23. Kalashnikov V V., Tomilova L G., Mendeleev Commun. 2007 17 343
24. Sperger C A., Wanner K T., Tetrahedron 2009 65 5824
25. Wallace D J., Gibb A D., Cottrell I F., Kennedy D J., Brands K M. J., Dolling U H., Synthesis 2001 1784