Structure-reactivity relationship in 19-methyl- and 19-nor-5,10-secosteroids. Part 4. Intramolecular nitrone 1,3-dipolar cycloadditions

Tetrahedron

Volumn 52, Issue 36, 1996, Pages 11995-12008

  Mihailović, Mihailo Lj ^a   Rajković, Milica M ^a   Lorenc, Ljubinka B ^a   Pavlović, Vladimir D ^a   Milovanović, Aleksandar Ž ^a   Tinant, Bernard ^b   Declercq, Jean Paul ^b  

^a UNIVERSITY OF BELGRADE   (Serbia)

^b UNIVERSITÉ CATHOLIQUE DE LOUVAIN   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

SECOSTEROID;

ARTICLE; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY; X RAY ANALYSIS;

EID: 0030565489     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00694-1     Document Type: Article

References (25)

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3. c. Akhtar, M.; Marsh, S. J. Chem. Soc. (C), 1966, 937-942.
4. 2. Mihailović, M. Lj.; Lorenc, Lj.; Rajković, M.; Juranić, I.; Milovanović, A. Heterocycles, 1989, 28, 869-878.
5. 3. a. Grigg, R.; Thianpantangul, S. J. Chem. Soc. Perkin Trans. I, 1984, 653-656.
6. b. Padwa, A.; Chiacchio, U.; Dean, D. C.; Schoffstahl, A. M.; Hassner, A.; Murthy, K. S. K. Tetrahedron Lett., 1988, 29, 4169-4172.
7. c. Bishop, J. E.; Flaxman, K. A.; Orlek, B. S.; Sammes, P. G. J. Chem. Soc. Perkin Trans. 1, 1995, 2551-2555.
8. 4. Huisgen, R. Angew. Chem. Int. Ed. Engl., 1963, 2, 633-645. Tufariello, J. J. in "1,3-Dipolar Cycloaddition Chemistry", Padwa, A., Ed., Wiley-Interscience, New York, Vol. 2, 1984.
9. 4. Huisgen, R. Angew. Chem. Int. Ed. Engl., 1963, 2, 633-645. Tufariello, J. J. in "1,3-Dipolar Cycloaddition Chemistry", Padwa, A., Ed., Wiley-Interscience, New York, Vol. 2, 1984.
10. 5. Mihailović, M. Lj.; Lorenc, Lj.; Maksimović, Z.; Kalvoda, J. Tetrahedron, 1973, 29, 2683-2692.
11. 6. Mez, H.-Ch.; Rist, G.; Ermer, O.; Lorenc, Lj.; Kalvoda. J.; Mihailović, M. Lj. Helv. Chim. Acta, 1976, 59, 1273-1293.
12. 7. Fuhrer, H.; Lorenc, Lj.; Pavlović, V.; Rihs, G.; Rist, G.; Kalvoda, J.; Mihailović, M. Lj. Helv. Chim. Acta, 1981, 64, 703-715.
13. 9
14. 9. Lorenc, Lj.; Bondarenko, L.; Rajković, M.; Milovanović, A.; Mihailović, M. Lj. Tetrahedron, 1983, 39, 3609-3614.
15. 10. Tinant, B.; Declercq, J.-P.; Lorenc, Lj.; Rajković, M.; Milovanović, A.; Mihailović, M. Lj. Bull. Soc. Chim. Belg., 1992, 101, 953-958.
16. 11. Tinant, B.; Declercq, J.-P.; Lorenc, Lj.; Rajković, M.; Milovanović, A.; Mihailović, M. Lj. Bull. Soc. Chim, Belg., 1992, 101, 771-774.
17. 12. Sheldrick, G. M. (1985). SHELXS86. In Crystallographic Computing 3, edited by G. M. Sheldrick, C. Kruger & R. Goddard, pp. 175-189. Oxford Univ. Press.
18. 13. Sheldrick, G. M. (1976). SHELX76. Program for crystal structure determination. Univ. of Cambridge, England.
19. 14. Spek A. L.(PLATON1990) Acta Crystall. A46, C-34.
20. 15. Tinant, B.; Declercq, J.-P.; Van Meersschee, M.; Mihailović, M. Lj.; Lorenc, Lj.; Rajković, M.; Milovanović, A. Bull. Soc. Chim. Belg., 1988, 97, 485-491.
21. 7,9
22. 17. Failure of (Z)-seco ketones 1 and 11 to undergo transannular cycloaddition with hydroxylamine hydrochloride may be due to insufficient stabilization of the transition state for isoxazolidine ring closure of the 1,3-dipolar oxime tautomer in conformation B (Scheme 5, R' = H).
23. 18. About details on the proposed mechanism see Ref. 19.
24. 19. Pavlović, V.; Rajković, M.; Lorenc, Lj.; Mihailović, M. Lj. J. Serb. Chem. Soc., 1994, 59, 903-907.
25. 13C-NMR at 360 MHz) at Ciba-Geigy Limited, Basel, Switzerland (Dr. H. Fuhrer) and (IR and mass) in the laboratories for Instrumental Analysis, Faculty of Chemistry, Belgrade.