Asymmetric 1,3-dipolar reactions of 3-sulfinylfuran-2(5H)-ones with 11H-dibenzo[b,e]azepine 5-oxide. Synthesis of pyrroloazepines via isoxazoloazepines

Tetrahedron Letters

Volumn 45, Issue 24, 2004, Pages 4653-4656

  García Ruano, José L ^a   Andrés Gil, J Ignacio ^b   Fraile, Alberto ^a   Martín Castro, Ana María ^a   Martín, M Rosario ^a  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

^b Johnson Johnson Pharmaceutical R D   (Spain)

Author keywords

1,3 Dipolar reaction; Dibenzoazepines; Pyrroloazepines; Sulfoxides

Indexed keywords

11H DIBENZ[B,E]AZEPINE 5 OXIDE; AZEPINE DERIVATIVE; DOPAMINE RECEPTOR; FURANONE DERIVATIVE; G PROTEIN COUPLED RECEPTOR; ISOXAZOLOAZEPINE; MORPHANTHRIDINE N OXIDE; OXIDE; PIPERIDINE DERIVATIVE; PYRROLE DERIVATIVE; SEROTONIN RECEPTOR; UNCLASSIFIED DRUG;

ADDITION REACTION; ARTICLE; BINDING AFFINITY; CRYSTALLIZATION; DECOMPOSITION; DIASTEREOISOMER; DRUG RECEPTOR BINDING; DRUG SYNTHESIS; STEREOCHEMISTRY; STEREOISOMERISM; X RAY ANALYSIS;

STAPHYLOCOCCUS PHAGE 3A;

EID: 2442672563     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.04.108     Document Type: Article

References (33)

1. Guzikowski A.P., Espitia S.A., Hawkinson J.E., Huettner J.E., Nogales D.F., Wodward R.M., Weber E., Keana C. J. Med. Chem. 39:1996;4643-4653. and references cited therein
2. Link A., Kunick C. J. Med. Chem. 41:1998;1299-1305. and references cited therein
3. Andrés J.I., Alcázar J., Alonso J.M., Díaz A., Fernández J., Gil P., Iturrino L., Matesanz E., Meert T.F., Megens A., Sipido V.K. Bioorg. Med. Chem. Lett. 12:2002;243-248
4. Andrés J.I., Alcázar J., Alonso J.M., Diaz A., Fernández J., Gil P., Iturrino L., Matesanz E., Meert T.F., Megens A., Sipido V.K. Bioorg. Med. Chem. Lett. 12:2002;249-253
5. Nickolson V.J., Wieringa J.H. J. Pharm. Pharmacol. 33:1981;760-766
6. Mizuno A., Miya M., Kamei T., Shibata M., Tatsuoka T., Nakanishi K., Takiguchi C., Hidaka T., Yamaki A., Inomata N. Chem. Pharm. Bull. 48:2000;1129-1137
7. (c) Mizuno, A.; Shibata, M.; Iwamori, T.; Shimamoto, T.; Nakanishi, K.; Inomata, N. U.S. Patent No 875, 495, 2001; Chem. Abstr. 2001, 135, 92553
8. Tufariello J.J. Padwa A. 1, 3-Dipolar Cycloaddition Chemistry. Vol. 2:1984;83-168 John Wiley & Sons, New York
9. Frederickson M. Tetrahedron. 53:1997;403-425
10. Gothelf K.V., Jørgensen K.A. Chem. Rev. 98:1998;863-909
11. García Ruano J.L., Cid B. Top. Curr. Chem. 204:1999;1-126. (Organosulfur Chemistry I)
12. García Ruano J.L., Carreño M.C., Toledo M.A., Aguirre J.M., Aranda M.T. Angew. Chem., Int. Ed. 39:2000;2736-2737
13. García Ruano J.L., Alemán J., Soriano J.F. Org. Lett. 5:2003;677-680
14. García Ruano J.L., Alemán J. Org. Lett. 5:2003;4513-4516
15. García Ruano J.L., Alemparte C. J. Org. Chem. 69:2004;1405-1408
16. Carretero J.C., García Ruano J.L., Lorente A., Yuste F. Tetrahedron: Asymmetry. 2:1993;177-180
17. García Ruano J.L., Fraile A., Martín M.R. Tetrahedron: Asymmetry. 7:1996;1943-1950
18. García Ruano J.L., Fraile A., González G., Martín M.R., Clemente F.R., Gordillo R. J. Org. Chem. 68:2003;6522-6534
19. García Ruano J.L., Fraile A., Martín M.R. Tetrahedron. 55:1999;14491-14500
20. (a) García Ruano J. L.; Fraile, A.; Martín, M. R. In 19th International Symposium Organic Chemistry of Sulfur, Book of Abstracts, 2000; pp 26
21. García Ruano J.L., Tito A., Peromingo M.T. J. Org. Chem. 68:2003;10013-10019
22. García Ruano J.L., Tito A., Peromingo M.T. J. Org. Chem. 67:2002;981-987
23. Louis C., Hootelé C. Tetrahedron: Asymmetry. 8:1997;109-131. and references cited therein
24. Aggarwal V.K., Roseblade S., Barrell J.K., Alexander K. Org. Lett. 4:2002;1227-1229
25. Rispens M.T., Keller E., de Lange B., Zijlstra W.J., Feringa B.L. Tetrahedron Asymmetry. 4:1994;607-624. and references cited therein
26. 3a (Scheme 2), is related to the face of the dipolarophile, which is attacked by the dipole, using as a reference the spatial arrangement of the ethoxy group. The endo- or exo-terms, indicative of the cis- or trans-arrangement exhibited by furanone and azepine moieties at the isoxazolidine ring, are related to the endo- and exo-addition modes of the dipole, using the ester group at the furanone ring as a reference
27. Merenda I., Ottana R., Romeo G., Rotondo E. Heterocycles. 29:1989;547-555
28. Burdisco M., Gamba A., Gandolfi R., Pevarelo P. Tetrahedron. 44:1988;3735-3748
29. Crystallographic data (excluding structure factors) for anti-3a-endo have been deposited with the Cambridge Crystallographic Data Centre as suplementary publication number CCDC 190809. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44(0)-1223-366033 or e-mail: deposit@ccdc.cam.ac.uk]
30. Schenck G.O. Liebigs Ann. 584:1953;156-176
31. Tufariello J.J., Tette J. J. Org. Chem. 40:1975;3866-3869
32. Kubáň J., Kolarovič A., Fišera L., Jäger V., Humpa O., Prónayová N. Synlett. 2001;1866-1868
33. The in vitro screening of the compounds was performed at Johnson & Johnson Pharmaceutical Research & Development, Division of Janssen Pharmaceutica N.V., Turnhoutsweg 30, B2340 Beerse, Belgium. The authors would like to acknowledge support from this company