Ring transformation of 1,5-diazabicyclo[3.1.0]hexanes under the action of arylketenes

Journal of Heterocyclic Chemistry

Volumn 43, Issue 4, 2006, Pages 881-888

  Shevtsov, Alexander V ^a   Kuznetsov, Vladimir V ^a   Kislukhin, Alexander A ^a   Petukhova, Vera Yu ^a   Strelenko, Yu A ^a   Makhova, Nina N ^a   Lyssenko, Konstantin A ^b  

^a N D ZELINSKY INSTITUTE OF ORGANIC CHEMISTRY   (Russian Federation)

^b A N NESMEYANOV INSTITUTE OF ORGANOELEMENT COMPOUNDS   (Russian Federation)

Author keywords

[No Author keywords available]

Indexed keywords

1,5 DIAZABICYCLO[3.1.0]HEXANE; 1,5 DIAZABICYCLO[3.2.1]OCTAN 6 ONE; 1,5 DIAZABICYCLO[3.3.0]OCTANE 2 ONE; 2 (4 CHLOROPHENYL)TETRAHYDRO 1H,5H PYRAZOLO[1,2 A]PYRAZOL 1 ONE [3 (4 CHLOROPHENYL) 1,5 DIAZABICYCLO[3.3.0]OCTAN 2 ONE]; 2,2 DIPHENYLTETRAHYDRO 1H,5H PYRAZOLO[1,2 A]PYRAZOL 1 ONE (3,3 DIPHENYL 1,5 DIAZABICYCLO[3.3.0]OCTAN 2 ONE); AZIRIDINE DERIVATIVE; BICYCLO COMPOUND; HETEROCYCLIC COMPOUND; HEXANE; KETENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE; X RAY CRYSTALLOGRAPHY;

EID: 33747401639     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570430411     Document Type: Article

References (34)

1. E. Schmitz, "Three-membered rings with two heteroatoms", Advances in Heterocycl. Chem., 24, 63 (1979).
2. E. Schmitz, Three-membered rings with two heteroatoms and fused-ring derivatives, Comprehensive Heterocycl. Chem., ed. W. Lwowski, Pergamon press, 1, 195 (1984).
3. H. W. Heine, "Diaziridines, 3H-Diazirines, Diaziridinones and Diaziridinimines", Small ring Heterocycles, part 2, ed. A. Hassner, Wiley-Interscience, chapter IV, pp. 547-629 (1983).
4. R. Kostyanovsky, R. Murugan and M. Sutharchanadevi, "Diaziridines and diazirines", Comprehensive Heterocycl. Chem. II, ed. A. Padwa, Pergamon press, 1A, pp. 348-364 (1996).
5. A. P. Molchanov, D. I. Sipkin, Yu. B. Koptelov and R. R. Kostikov, Synlett., 1779, (2000).
6. M. Schulz, G. West, U. Muller and D. Henke, J. Pract. Chem., 318, 946 (1976).
7. H. W Heine, R. H. Thomas, G. Paul and W. and R. Cowan Hoye, J. Org. Chem., 38, 2984 (1973).
8. B. Carbony, L. Toupet and R. Carrie, Tetrahedron, 43, 2293 (1987).
9. E. V. Dehmlov and J. Schonefeld, Z. Naturforsch. 30B: Anorg. Chem., Org. Chem., 824 (1975).
10. P. G. Kostyanovsky, K. S. Zakharov, M. Zaripova and V. F. Rudchenko, Izv. Akad. Nauk SSSR, Ser. Khim. (in Russian), 875 (1975);
11. [Bull. Acad. Sci. USSR, Div. Chem. Sci. (Engl. Transl.) 24, 791 (1975).]
12. M. Komatsu, N. Nishikaze, M. Sakamoto, Y. Ohshiro and T. Agawa, J. Org. Chem., 22, 3198 (1974).
13. [a] A. V. Shevtsov, V. Yu. Petukhova, Yu. A. Strelenko, K. A. Lyssenko, I. V. Fedyanin and N. N. Makhova, Mendeleev Commun., 221 (2003)
14. [b] A. V. Shevtsov, V. Yu. Petukhova, Yu. A. Strelenko, K. A. Lyssenko, N. N. Makhova and Tartakovsky, Izv. Akad. Nauk, Ser. Khim., (in Russian), 997 (2005)
15. [Rus. Chem. Bull., Int. Ed., 1021 (2005)]
16. [c] A. V. Shevtsov, V. Yu. Petukhova, Yu. A. Strelenko and N. N. Makhova, Mendeleev Commun., 29 (2005).
17. L. Fieser and M. Fieser, "Reagents for Organic Synthesis", M. Mir, 1, p. 393 (1970) (in Russian).
18. D. E. Davies and R. C. Storr, Compehensive Heterocycl. Chem., ed. W. Lwowski, Pergamon press 1, 237-284 (1984).
19. G. V. Shustov, S. N. Denisenko, I. I. Chervin, N. L. Astandiarov and R. G. Kostyanovsky, Tetrahedron, 41, 5719 (1985).
20. A. Mannschreck and W. Seitz, Angew. Chem., 81, 224 (1969).
21. H. Borme, E. Mundlos, and O. E. Herboth, Chem. Ber., 90, 2003 (1957).
22. J. E. Baldwin, J. Chem. Soc., Chem. Commun., 734 (1976).
23. L. L. Rodina, A. B. Khalikova, O. A. Verzhba, and I. K. Korobizina, Khim. Azometiniminov//Sovrem. Problemi organich. Khim., ed. K. A. Ogloblina, Izdatelstvo Leningradskogo univer., v.8, 135-171 (1986) (in Russian).
24. A. P. Molchanov, D. I. Sipkin, Yu. B. Koptelov and R. R. Kostikov, Zhurn. Org. Khim., 37, 888 ,(2001),
25. Synlett, 1779 (2000).
26. A. P. Molchanov, D. I. Sipkin, Yu. B. Koptelov and R. R. Kostikov, Eur. J. Org. Chem., 453 (2002).
27. L. N. Jungheim and S. K. Sigmund, J. Org. Chem., 52, 4007 (1987).
28. L. N. Jungheim, Tetrahedron Lett, 30, 1889 (1989).
29. T. Toya, K. Yamaguchi, Y. Endo, Bioorg. Med. Chem., 953 (2002).
30. M. J. Laufersweiler, T. A. Brugel, M. P. Clark, A. Golebiowski, R. G. Bookland, S. K. Laughlin, M. P. Sabat, J. A. Townes, J. C. VanRens, B. De, L. C. Hsieh, S. A. Heitmeyer, K. Juergens, K. K. Brown, M. J. Mekel, R. L. Walter, and M. J. Janusz, Bioorg. Med. Chem. Lett., 14, 4267, (2004).
31. M. P. Clark, S. K. Laughlin, M. J. Laufersweiler, R. G. Bookland, T. A. Brugel, A. Golobiowski, M. P. Sabat, J. A. Townes, J. C. VanRens, J. F. Djung, M. G. Natehus, B. De, L. C. Hsieh, S. C. Xu, R. L. Walter, M. J. Mekel, S. A. Heitmeyer, K. K. Brown, K. Juergens, Ye. O. Taiwo, and M. J. Janusz, J. Med. Chem., 47, 2724 (2004).
32. SMART V5.051 and SAINT V5.00, Area detector control and integration software, Bruker AXS Inc., Madison, WI-53719, USA (1998).
33. G.M. Sheldrick, SADABS, Bruker AXS Inc., Madison, WI-53719, USA (1997).
34. G.M. Sheldrick, SHELXTL-97, Version 5.10, Bruker AXS Inc., Madison, WI-53719, USA.