Diels-Alder reactions of pyrimidine o-Quinodimethanes: Stereochemistry and applications to the synthesis of tetrahydro- and quinazoline derivatives

Letters in Organic Chemistry

Volumn 3, Issue 9, 2006, Pages 703-708

  Herrera, Antonio ^a   Martínez Alvarez, Roberto ^a   Chioua, Mourad ^a   Chioua, Rachid ^b   Almy, John ^c   Sánchez, Angel ^a  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

^b FACULTÉ DES SCIENCES   (Morocco)

^c CALIFORNIA STATE UNIVERSITY   (United States)

Author keywords

Diels Alder reaction; Pyrimidine ortho quinodimethanes; Quinazolines; Tetrahydroquinazolines

Indexed keywords

EID: 33750454079     PISSN: 15701786     EISSN: None     Source Type: Journal    
DOI: 10.2174/157017806778699955     Document Type: Article

References (33)

1. For recent reviews, see: (a) Collier, S.J.; Storr, R.C. Progress in Heterocyclic Chemistry; Gribble, G.W.; Gilchrist, T.L. Eds.; Pergamon: New-York, 1998, Vol. 10;
2. (b) Martin N.; Segura, J.L. Chem. Rev. 1999, 99, 3199-3246.
3. (a) Nicolaou, K.C.; Gray, D.L.F.; Tae, J. S. J. Am. Chem. Soc. 2004, 126, 613-627;
4. (b) Nicolaou, K.C.; Gray, D.L.F.; Tae, J.S. Angew. Chem. Int. Ed. 2001, 40, 3675-3678;
5. (c) Clive, D.L.J.; Wang, J. Org. Prep. Proced. Int. 2005, 37, 1-36.
6. (a) Gruber, J.; Li, R.W.C.; Aguiar, L.H.J.M.C; Benvenho, A.R.V.; Lessmann, R.; Hummelgen, I.A. J. Mat. Chem. 2005, 15, 517-522;
7. (b) Itoh, T.; Nomura, S.; Ohtake, M.; Yoshida, T.; Uno, T.; Kajiwara, A.; Sada, K.; Miyata, M. Macromolecules 2004, 37, 8230-8238.
8. (a) Aihara, J Bull. Chem. Soc. Jpn. 2005, 78, 443-444;
9. (b) Tang, K.C.; Lee, S.J.; Chi, S.H.; Lu, K.L.; Chen, W.C.; Yu, C. H.; Wu, S. L.; Chen, C.C.; Lin, W.D.; Chen, L.J.; Wang, N.S.; Chung, W.S. J. Photochem. Photobiol., A 2005 170, 69-81.
10. (a) Terzidis, M.; Tsoleridis, C.A.; Stephanidou-Stephanatou, J. Tetrahedron Lett. 2005, 46, 7239-7242;
11. (b) Vessels, J.T.; Janicki, S.Z.; Petillo, P.A. Org. Lett. 2000, 2, 73-76.
12. Konstantinidou, D.; Papageorgiou, M.; Stephanidou-Stephanatou, J.; Tsoleridis, C.A. Tetrahedron Lett. 2005, 46, 4843-4845.
13. Zhao, S.X.; Neves, M.G.P.M.S.; Tome, A.C.; Silva, A.M.S.; Cavaleiro, J.A.S.; Domingues, M.R.M.; Ferrer, A.J.F. Tetrahedron Lett. 2005, 46, 2189-2191.
14. (a) Herrera, A.; Martinez, R.; González, B.; Illescas, B.; Martin, N.; Seoane, C. Tetrahedron Lett. 1997, 38, 4873-4876;
15. (b); Ko, C.W.; Chou, T.S. Tetrahedron Lett. 1997, 30, 5315-5318;
16. (c) Mertzanos, G.R.; Stephanidou-Stephanatou, J.; Tsoleridis, C.A.; Alexandrou, N.E. Tetrahedron Lett. 1992, 33, 4499-4502;
17. (d) Sheperd, M.K. J. Chem. Soc. Perkin Trans. 1 1986, 1495-1498;
18. (e) Carly, P. R.; Cappelle, S.L.; Compernolle, F.; Hoomaert, G.J. Tetrahedron 1996, 52, 11889-11904.
19. (a) Cappelle, S.L.; Vogels, I.; Van Meervelt, L.; Compernolle, F.; Hoomaert, G.J. Tetrahedron Lett. 2001, 42, 3759-3762;
20. (b) Carly, P.R.; Govaerst, T.C.; Capelle, S.L.; Hoomaert, G.J. Tetrahedron 2001, 57, 4203-4212.
21. (a) Govaerts, T.C.; Vogels, I.; Compernolle, F.; Hoornaert, G. Tetrahedron Lett. 2002, 43, 799-802;
22. (b) Govaerts, T.C.; Vogels, I.; Compernolle, F.; Hoomaert, G. Tetrahedron 2003, 59, 5481-5494;
23. (c) Govaerts, T.C.; Vogels, I.; Compernolle, F.; Hoornaert, G. Tetrahedron 2004, 60, 429-439.
24. González, B.; Herrera, A.; Illeascas, B.; Martín, N.; Martínez, R.; Moreno, F.; Sánchez, L.; Sánchez, A. J. Org. Chem. 1998, 63, 6807-6813.
25. Durst, T.; Kozma, E. C.; Saegusa, T. J. Org. Chem. 1985, 50, 4829-4833.
26. (a) Li, C.T.; Chen, K-Z.; Chou, T-C. Tetrahedron 2003, 59, 1493-1500;
27. (b) Di Valentin, C.; Freccero, M.; Sarzi-Amadè, M.; Zanaletti, R. Tetrahedron 2000, 56, 2547-2559.
28. Choi, S.; Frank, W.; Ritter, H. React. Funct. Polym. 2006, 66, 149-156.
29. Turececk, F.; Hanus, V. Mass Spectrom. Rev. 1984, 3, 85-152.
30. Chioua, R.; Benabdelouahab, F.; Chioua, M.; Martínez-Alvarez, R.; Herrera, A. Molecules 2002, 7, 507-510.
31. Günther, H. In NMR Spectroscopy; John Wiley & Sons: Chichester, 1995; pp. 122-128.
32. Stang, P.J.; Dueber, T.E. Org. Synth. 1974, 54, 79-84
33. Stang, P.J.; Hanack, M.; Subramanian, L.R. Synthesis 1982, 85-126.