Synthesis and application of novel bicyclic guanidines: N-alkylation of 1,5,7-triazabicyclo[4.4.0]dec-5-ene

Arkivoc

Volumn 2000, Issue 3 SPEC.ISS., 2000, Pages 266-273

  Genski, Thorsten ^a   Macdonald, Gregor ^a   Wei, Xudong ^a   Lewis, Norman ^b   Taylor, Richard J K ^a  

^a UNIVERSITY OF YORK   (United Kingdom)

^b GLAXOSMITHKLINE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

1,5,7 TRIAZABICYCLO[4 4 0]DEC 5 ENE; 3 TERT BUTOXYCARBONYLAMINO 4,4 DIMETHOXYCYCLOHEXA 2,5 DIEN 1 ONE; BUTYL HYDROPEROXIDE; CAMPHOR; CHALCONE; GUANIDINE DERIVATIVE; NUCLEOSIDE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; ENANTIOMER; EPOXIDATION; PROTON TRANSPORT; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0001019447     PISSN: 14246376     EISSN: 14246376     Source Type: Journal    
DOI: None     Document Type: Article

References (34)

1. (a) Corey, E. J.; Grogan, M. J. Org. Lett. 1999, 1, 157;
2. (b) Alcázar, V.; Morán, J. R.; de Mendoza, J. Tetrahedron Lett. 1995, 36, 3941;
3. (c)Chinchilla, R.; Nájera, C.; Sánchez-Agullá, P. Tetrahedron: Asymmetry 1994, 5, 1393.
4. (a) Kurzmeier, H.; Schmidtchen, F. P. J. Org. Chem. 1990, 55, 3749;
5. (b) Schmidtchen, F. P.; Berger, M. Chem. Rev. 1997, 97, 1609.
6. Preliminary communication on part of this work: Genski, T.; Macdonald, G.; Wei, X.; Lewis, N.; Taylor, R. J. K. Synlett 1999, 795.
7. (a) Taylor, R. J. K.; Alcaraz, L.; Kapfer-Eyer, I.; Macdonald, G.; Wei, X.; Lewis, N. Synthesis 1998, 775;
8. (b) Alcaraz, L.; Macdonald, G.; Ragot, J. P.; Lewis, N.; Taylor, R. J. K. J. Org. Chem. 1998, 63, 3526 and Tetrahedron 1999, 55, 3707;
9. (b) Alcaraz, L.; Macdonald, G.; Ragot, J. P.; Lewis, N.; Taylor, R. J. K. J. Org. Chem. 1998, 63, 3526 and Tetrahedron 1999, 55, 3707;
10. (c) Macdonald, G.; Alcaraz, L.; Lewis, N. J.; Taylor, R. J. K. Tetrahedron Lett. 1998, 39, 5433;
11. (d)Dwyer, C. L.; Gill, C. D.; Ichihara, O.; Taylor, R. J. K. Synlett. 2000, 704.
12. (a) Schlessinger, R. H.; Bebernitz, G. R.; Lin, P.; Poss, A. J. J. Am. Chem. Soc. 1985, 107, 1777;
13. (b) Yadav, V. K.; Kapoor, K. K. Tetrahedron 1995, 51, 8573.
14. Horváth, A. Tetrahedron Lett. 1996, 37, 4423.
15. (a) Alder, R. W.; Mowlam, R. W.; Vachon, D. J.; Weisman, G. R. J. Chem. Soc., Chem. Commun. 1992, 507;
16. (b) Kosasayama, A.; Konno, T.; Higashi, K.; Ishikawa, F. Chem. Pharm. Bull. 1979, 27, 841.
17. Subba Rao, Y. V.; De Vos, D. E.; Jacobs, P. A. Angew. Chem. Int. Ed. Engl. 1997, 36, 2661.
18. (a) Anderson, S. R.; Ayers, J. T.; DeVries, K. M.; Ito, F.; Mendenhall, D.; Vanderplas, B. C. Tetrahedron: Asymmetty 1999, 10, 2655
19. (b) Gorzynski Smith, J. Synthesis 1984, 629.
20. Gravier-Pelletier, C.; Bourissou, D.; Le Merrer, Y.; Depezay, J.-C. Synlett 1996, 275.
21. (a) Casey, M.; Moody, C. J.; Rees, C. W. J. Chem. Soc., Chem. Commun. 1982, 714;
22. (b) Fiorenza, M.; Ricci, A.; Taddei, M.; Tassi, D. Synthesis 1983, 640.
23. Onaka, M.; Kawai, M.; Izumi, Y. Chem. Lett. 1985, 779.
24. Chini, M.; Crotti, P.; Favero, L.; Macchia, F.; Pineschi, M. Tetrahedron Lett. 1994, 35, 433.
25. Iranpoor, N.; Tamami, B.; Niknam, K. Can. J. Chem. 1997, 75, 1913.
26. Vidal-Ferran, A.; Moyano, A.; Pericàs, M. A.; Riera, A. J. Org. Chem. 1997, 62, 4970.
27. Choshi, T.; Yamada, S.; Sugino, E.; Kuwada, T.; Hibino, S. J. Org. Chem. 1995, 60, 5899.
28. (a) Dimitrov, V.; Bratovanov, S.; Simova, S.; Kostova, K Tetrahedron Lett. 1994, 35, 6713
29. (b) Dimitrov, V.; Simova, S.; Kostova, K Tetrahedron 1996, 52, 1699.
30. For lead references see: (a) Enders, D.; Zhu, J.; Kramps, L. Liebigs Ann./Recueil 1997, 1101;
31. (b) Watanabe, S.; Arai, T.; Sasai, H.; Bougauchi, M.; Shibasaki, M. J. Org. Chem. 1998, 63, 8090;
32. (b) Elston, C. L.; Jackson, R. F. W.; MacDonald, S. J. F.; Murray, P. J. Angew. Chem. Int. Ed. Engl. 1997, 36, 410
33. (d) Corey, E. J.; Zhang, F.-Y. Org. Lett. 1999,1, 1287
34. (e) Porter, M. J.; Roberts, S. M.; Skidmore, J. Bioorg. Med. Chem. 1999, 7, 2145.