Dipole-stabilized carbanions in series of cyclic aldonitrones. Part 2: Reactions of the metalated aldonitrones - Derivatives of 3-imidazoline 3- oxide and 2H-imidazole 1-oxide with aldehydes and ketones

Tetrahedron

Volumn 56, Issue 24, 2000, Pages 4071-4077

  Voinov, Maxim A ^a   Grigor'Ev, Igor A ^a   Volodarsky, Leonid B ^a  

^a N N VOROZHTSOV NOVOSIBIRSK INSTITUTE OF ORGANIC CHEMISTRY   (Russian Federation)

Author keywords

hydroxymethyl nitrones; 1,3 dipolar cycloaddition; 2H imidazole 1 oxide; 3 imidazoline 3 oxide; Dipole stabilized organolithiums; Metalation; Nitrones

Indexed keywords

(1,2,2,5,5 PENTAMETHYL 2,5 DIHYDRO 1H IMIDAZOL 4 YL)PHENYLMETHANONE; 3 IMIDAZOLINE 3 OXIDE; 3,3,8 TRIMETHYL 1 PHENYL 5A,6,7,8 TETRAHYDRO 3H,5H 4 OXA 2,3A DIAZA CYCLOPENTA[C]PENTALEN 8 OL; ALDEHYDE; HYDROGEN; IMIDAZOLE DERIVATIVE; KETONE; NITRONE; OXIDE; PIPERIDINE DERIVATIVE; UNCLASSIFIED DRUG;

ACIDITY; ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; PRIORITY JOURNAL; SYNTHESIS;

EID: 0034625365     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(00)00321-5     Document Type: Article

References (37)

1. Brown R.F.C., Clark V.M., Todd A. Sir. J. Chem. Soc. 1965;2337-2340.
2. Boocock D.G., Darcey B.R., Ullman E.F. J. Am. Chem. Soc. 90:1968;5945-5946.
3. (a) Kliegel, W. Pharmazie, 1978, 33 (6), 331-335.
4. (b) Johnson, C. R.; Taylor, J. D.; Honn, K. V.; Cheng, S. US Patent US4,758,669. Appl. 859,694,05. Chem. Abstr. 1988, 109 (17), 149366a.
5. (c) Anana, R. D.; Ng, H.; Hawlett, S. E.; Knaus, E. E. Arch. Pharm. Pharm. Med. Chem., 1997, 330 (3), 53-58.
6. (d) Ellwood, C. W.; Tikhonov, A. Ya. PCT Int. Appl. WO9803,479. Chem. Abstr. 1998, 128 (13), 153919t.
7. (e) Tikhonov, A. Ya.; Mazhukin, D. G.; Grigor'eva, L. N.; Khlestkin, V. K.; Voinova, N. N.; Syropyatov, B. Ya.; Shrinkina, S. S.; Volodarsky, L. B. Arch. Pharm. Pharm. Med. Chem., 1999, 332 (9), 305-308.
8. Torssell, K. B. G. Nitrile Oxides, Nitrones, and Nitronates in Organic Synthesis, VCH Publishers, 1988.
9. Martin, V. V.; Volodarskii, L. B. Khim. Geterotsikl. Soedin., 1979, 1, 103-109. Chem. Abstr. 1979, 90, 186860s.
10. Martin, V. V.; Volodarskii, L. B. Khim. Geterotsikl. Soedin., 1979, 1, 103-109. Chem. Abstr. 1979, 90, 186860s.
11. (a) Kirilyuk, I. A.; Grigor'ev, I. A.; Volodarskii, L. B. Izv. Akad. Nauk. SSSR. Ser. Khim., 1991, 9, 2122-2127. Chem. Abstr. 1991, 115, 279911j;
12. (a) Kirilyuk, I. A.; Grigor'ev, I. A.; Volodarskii, L. B. Izv. Akad. Nauk. SSSR. Ser. Khim., 1991, 9, 2122-2127. Chem. Abstr. 1991, 115, 279911j;
13. (b) Volodarsky, L. B.; Tikhonov, A. Ya. Synthesis 1986, 704-715.
14. (a) Putsykin, Yu. G.; Volodarskii, L. B. Izv. Sib. Otd. Akad. Nauk. SSSR. Ser. Khim., 1969, 9 (4), 86-93. Chem. Abstr. 1970, 72, 54514a.
15. (a) Putsykin, Yu. G.; Volodarskii, L. B. Izv. Sib. Otd. Akad. Nauk. SSSR. Ser. Khim., 1969, 9 (4), 86-93. Chem. Abstr. 1970, 72, 54514a.
16. (b) Volodarskii, L. B.; Lysak, A. N.; Koptyug, V. A. Khim. Geterotsikl. Soedin., 1968, 2, 334-338. Chem. Abstr. 1968, 69, 96577s.
17. (b) Volodarskii, L. B.; Lysak, A. N.; Koptyug, V. A. Khim. Geterotsikl. Soedin., 1968, 2, 334-338. Chem. Abstr. 1968, 69, 96577s.
18. (c) Kirilyuk, I. A.; Grigor'ev, I. A.; Petrenko, O. P.; Volodarskii, L. B. Izv. Akad. Nauk. SSSR. Ser. Khim., 1993, 12, 2096-2100.
19. (d) Samsonov, V. A.; Volodarskii, L. B. Khim. Geterotsikl. Soedin., 1980, 6, 808-813. Chem. Abstr. 1980, 93, 186242d.
20. (d) Samsonov, V. A.; Volodarskii, L. B. Khim. Geterotsikl. Soedin., 1980, 6, 808-813. Chem. Abstr. 1980, 93, 186242d.
21. Volodarsky L.B., Grigor'ev I.A. Synthesis of Heterocyclic Nitroxides. Volodarsky L.B., Imidazoline Nitroxides. 1:1988;5-28 CRC Press, Boca Raton. Chap. 2.
22. Döpp, D., Döpp, H., Nitrones. In: Methoden der Organischen Chemie (Houben-Weyl); Klamann, D., Hagemann, H., Eds.; Georg Thieme Verlag: Stuttgart: New York, 1990; Bd. E14b, Teil 2, S. 1372-1544.
23. Voinov M.A., Grigor'ev I.A., Volodarsky L.B. Heterocycl. Comm. 4:(3):1998;261-270.
24. Mitasov, M. M.; Grigor'ev, I. A.; Shchukin, G. I.; Korobeinicheva, I. K.; Volodarskii, L. B. Izv. Sib. Otd. Akad. Nauk. SSSR. Ser. Khim., 1978, 2 (1), 112-116. Chem. Abstr. 1978, 88(26), 200214b.
25. Mitasov, M. M.; Grigor'ev, I. A.; Shchukin, G. I.; Korobeinicheva, I. K.; Volodarskii, L. B. Izv. Sib. Otd. Akad. Nauk. SSSR. Ser. Khim., 1978, 2 (1), 112-116. Chem. Abstr. 1978, 88(26), 200214b.
26. 13C NMR signals were made with the use of data for compounds with related tricyclic carbon skeleton: Weyerstahl, P.; Marschall, H.; Seelmann, I.; Jakupovic, J. Eur. J. Org. Chem., 1998, 1205-1212.
27. Clark B.A.J., Evans T.J., Simmonds R.G. J. Chem. Soc. Perkin Trans. I. 18:1975;1803-1806.
28. Grigor'ev, I. A.; Martin, V. V.; Shchukin, G. I.; Mamatyuk, V. I.; Volodarskii, L. B. Khim. Geterotsikl. Soedin., 1985, 2, 247-251. Chem. Abstr. 1985, 103 (1), 5831b.
29. Grigor'ev, I. A.; Martin, V. V.; Shchukin, G. I.; Mamatyuk, V. I.; Volodarskii, L. B. Khim. Geterotsikl. Soedin., 1985, 2, 247-251. Chem. Abstr. 1985, 103 (1), 5831b.
30. Grigor'ev, I. A.; Mamatyuk, V. I.; Shchukin, G. I.; Martin, V. V.; Volodarskii, L.B. Khim. Geterotsikl. Soedin., 1986, 8, 1065-1072. Chem. Abstr. 1987, 106 (21), 175673f.
31. Grigor'ev, I. A.; Mamatyuk, V. I.; Shchukin, G. I.; Martin, V. V.; Volodarskii, L.B. Khim. Geterotsikl. Soedin., 1986, 8, 1065-1072. Chem. Abstr. 1987, 106 (21), 175673f.
32. Hamer J., Macaluso A. Chem. Rev. 64:1964;473-495.
33. Klemmensen P., Schroll G., Lawesson S.-O. Ark. Kemi. 28:1968;405-411.
34. Grigor'ev, I. A.; Volodarskii, L.B. Zh. Org. Khim., 1975, 11 (6), 1328-1332. Chem. Abstr. 1975, 83 (25), 206157d.
35. Grigor'ev, I. A.; Volodarskii, L.B. Zh. Org. Khim., 1975, 11 (6), 1328-1332. Chem. Abstr. 1975, 83 (25), 206157d.
36. Castagnoli N. Jr, Cymerman J.C., Melikian A.P., Roy S.K. Tetrahedron. 26:1970;4319-4327.
37. 13C Nuclear Magnetic Resonance Spectroscopy in Natural Products Chemistry. In Progress in the Chemistry of Organic Natural Products; Springer-Verlag: 1979; 36, pp 24-33.