Reactivity of 5-hydroxy-5,6-dihydro-4H-pyrazines-easy and efficient access to ring-fused polycyclic diazinic systems

Tetrahedron Letters

Volumn 50, Issue 26, 2009, Pages 3679-3682

  Claveau, Elise ^a   Gillaizeau, Isabelle ^a   Coudert, Gérard ^a  

^a UNIVERSITÉ D'ORLÉANS   (France)

Author keywords

1,4 Diazine; Indole alkaloids; MICHAEL addition; Oxazine; Pyrazine

Indexed keywords

CARBOXYLIC ACID; PYRAZINE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; SYNTHESIS;

EID: 65549166550     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2009.03.152     Document Type: Article

References (25)

1. For diversity-oriented synthesis, see:. Tan D.S. Nat. Chem. Biol. 1 (2005) 74-84
2. Burke M.D., and Schreiber S.L. Angew. Chem., Int. Ed. 43 (2004) 46-58
3. Schreiber S.L. Science 287 (2000) 1964-1969
4. Mousset D., Gillaizeau I., Sabatié A., Bouyssou P., and Coudert G. J. Org. Chem. 71 (2006) 5993-5999
5. Mousset D., Gillaizeau I., Hassan J., Lepifre F., Bouyssou P., and Coudert G. Tetrahedron Lett. 46 (2005) 3703-3705
6. Claveau E., Gillaizeau I., Blu J., Bruel A., and Coudert G. J. Org. Chem. 72 (2007) 4832-4836
7. Cottineau B., Gillaizeau I., Farard J., Auclair M.-L., and Coudert G. Synlett (2007) 1925-1929
8. Chaignaud M., Gillaizeau I., Ouhamou N., and Coudert G. Tetrahedron 64 (2008) 8059-8066
9. Claveau E., Gillaizeau I., and Coudert G. Synlett 2 (2009) 263-267
10. Claveau, E.; Gillaizeau, I.; Kalinowska, J.; Bouyssou, P.; Coudert, G. 2009 (ASAP) doi:10.1021/jo900291f.
11. The necessary primary amine was prepared from 4-azamelatonin by deprotection of the corresponding acetamide by KOH/EtOH. See:. Jeanty M., Suzenet F., and Guillaumet G. J. Org. Chem. 73 (2008) 7390-7393
12. Royer J., Bonin M., and Micouin L. Chem. Rev. 104 (2004) 2311-2352
13. Enders D., and Shilvock J.P. Chem. Rev. 29 (2000) 359-373
14. Recent reviews:. Avendaño C., and Menéndez J.C. Curr. Org. Chem. 7 (2003) 149-173
15. Mhaske S.B., and Argade N.P. Tetrahedron 62 (2006) 9787-9826
16. Eguchi S. Top. Heterocycl. Chem. 6 (2006) 113-156
17. Wong S.-M., Musza L.L., Kydd G.C., Kullnig R., Gillum A.M., and Cooper R. J. Antibiot. 46 (1993) 545-553
18. Fujimoto H., Negishi E., Yamaguchi K., Nishi N., and Yamazaki M. Chem. Pharm. Bull. 44 (1996) 1843-1848
19. Brown, R. T. Indoles. The Monoterpenoid Indole Alkaloids; Saxton, J. E., Ed. In The Chemistry of Heterocyclic Compounds; Weissberger, A., Taylor, E. C., Eds.; Wiley: New York, 1983; Vol. 25, Part 4, Chapter 3.
20. Szántay C., Blaskó G., Honty K., and Dörnyei G. In: Brossi A. (Ed). The Alkaloids Vol. 27 (1986), Academic Press, London UK Chapter 2
21. Lounasmaa, M.; Tolvanen, A. In Monoterpenoid Indole Alkaloids; Saxton, J. E., Ed. In The Chemistry of Heterocyclic Compounds; Taylor, E. C., Ed.; Wiley: Chichester, UK, 1994; Vol. 25, Part 4, Chapter 3.
22. Amat M., Gòmez-Esqué A., Escolano C., Santos M.M., Molins E., and Bosch J. J. Org. Chem. 74 (2009) 1205-1211
23. Ma J., Yin W., Zhou H., Liao X., and Cook J.M. J. Org. Chem. 74 (2009) 264-273 and references cited herein
24. Compound 5c was isolated in low yield as the sole product. No regioisomer could be detected by NMR analysis. The low yield might have been partially due to the degradation of the starting compound.
25. Muhammad I., Dunbar D.C., Khan S.I., Tekwani B.L., Bedir E., Takamatsu S., Ferreira D., and Walker L. J. Nat. Prod. 66 (2003) 962-967