Rearrangement of α-hydroxylamino oximes to cyclic amidoximes by the action of sodium borohydride

Tetrahedron

Volumn 53, Issue 7, 1997, Pages 2527-2534

  Petukhov, Pavel A ^a   Denisov, Alexey Yu ^b   Tkachev, Alexey V ^a  

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

^b INSTITUTE OF CHEMICAL BIOLOGY AND FUNDAMENTAL MEDICINE   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

3 AZABICYCLO[4.1.1]OCTANE DERIVATIVE; 4 AZABICYCLO[5.1.0]OCTANE DERIVATIVE; OXIME; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DRUG STRUCTURE; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0031575614     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(96)01141-6     Document Type: Article

References (22)

1. 1 Petukhov, P.A.; Tkachev, A.V. Synlett 1993, 8, 580.
2. 2 Chow, Y.L. Canad. J. Chem. 1967, 45, 53-62.
3. 3 Glozman, O.M.; Voronina, T.A.; Orlova, E.K.; Meshcheryakova, L.M.; Rakhmankulova, I.K.; Kazanskaya, A.A.; Smirnov, L.D.; Rostock, A; Siegemund, H. Khim -Farm. Zh. 1989, 23, 1147-1152.
4. 4 Ray, S.M.; Lahiri, S.C. J. Indian Chem. Soc. 1991, 68, 549-555.
5. 5 Sindelar, K., Sedivy, Z.; Hrubantova, M.; Valchar, M., Metysova, J.; Protiva, M. Collect. Czech. Chem. Commun. 1988, 53, 381-388.
6. 6 Clement, B.; Raether, W. Arzneim -Forsch. 1985, 35, 1009-1014.
7. 7 Nicolaides, D.N.; Varella, E.A. The Chemistry of Amidoximes. Wiley, 1992, pp. 875-966.
8. 8 Blaser, H.-U. Chem. Rev. 1992, 92, 935-952.
9. 9 Volodarsky, L.B.; Putsykin, Y.G. Zh. Org. Khim. 1967, 3, 1686-1694.
10. 10 Enders, H.; Jannack, T.; Prickner, B. Acta Cryst. 1980, B36, 2230-2238.
11. 11 Krivdin, L.B.; Kalabin, G.A. Prog. Nucl. Magn. Reson. Spectrosc. 1989, 21, 293-448.
12. 2)-N(amide). This barrier is just the most important for the calculation of the cyclic amidoximes. The barrier seems to be lower than for amides, so MM calculations of cyclic amidoximes as lactams are inapplicable.
13. 13 Bliznuk, A.A.; Voituk, A.A. Zh. Strukt. Khim. 1986, 27, No. 4, 190-191.
14. 14 Chibirjaev, A.M.; Popov, S.A.; Tkachev, A.V. Mendeleev Communications 1996, No. 1, 18-20.
15. 15 Kalinowski, H.-O.; Berger, S.; Braun, S. Carbon-13 NMR Spectroscopy. Wiley, Chichester, 1988.
16. 16 Eckstein, Z.; Jelenski, P. Synth. Commun. 1982, 12, 201-208.
17. 17 Zabza, A.; Wawrzenczyk, C.; Kuczynski, H. Bull. Pol. Acad. Sci., Chem. 1974, 22, 855-862.
18. 18 Tikhonov, A.Ya.; Belova, N.V.; Volodarsky, L.B.; Gatilov, Yu.V. Zh. Org. Khim. 1985, 21, 196-203.
19. 19 The geometry of the imines was optimized by semi-empirical calculations. The most stable forms were those with E-configuration of the oxime moiety.
20. 20 Tkachev, A. V.; Rukavishnikov, A.V.; Chibiryaev, A.M.; Denisov, A.Yu.; Gatilov, Yu.V., Bagryanskaya, I.Yu. Austr. J. Chem 1992, 45, 1077-1086.
21. 21 Booth, S.E.; Jenkins, P.R.; Swain, Christopher J. J. Chem. Soc., Chem. Commun. 1993, 147-148.
22. 22 Rukavishnikov, A.V.; Tkachev, A.V.; Volodarsky, L.B.; Pentegova, V.A. Zh. Org. Khim. 1989, 25, 1665-1671.