Synthesis of enantiomerically pure, partly saturated (R S)-[(1S)-isoborneol-10-sulfinyl]-substituted [1,2,4]triazolo[1,2-a]pyridazine, cinnolines and benzo[f]cinnolines

Arkivoc

Volumn 2004, Issue 1, 2004, Pages 79-87

  Aversa, Maria Chiara ^a   Barattucci, Anna ^a   Bonaccorsi, Paola ^a   Caruso, Francesco ^a   Giannetto, Placido ^a  

^a UNIVERSITY OF MESSINA   (Italy)

Author keywords

1,2,4 triazolo 1,2 a cinnolines; 1,2,4 triazolo 1,2 a pyridazines; Benzo f 1,2,4 triazolo 1,2 a cinnolines; Diels Alder cycloaddition; Stereoselectivity; Sulfoxides

Indexed keywords

1 [1 (ISOBORNEOL 10 SULFINYL)VINYL]CYCLOHEXENE; 1,2 DIHYDRO 4 [1 (ISOBORNEOL 10 SULFINYL)VINYL] 7 METHOXYNAPHTHALENE; 1,2 DIHYDRO 4 [1 (ISOBORNEOL 10 SULFINYL)VINYL]NAPHTHALENE; 3 (ISOBORNEOL 10 SULFINYL) 1 METHOXYBUTA 1,3 DIENE; 4 PHENYL 1,2,4 TRIAZOLINE 3,5 DIONE; 5,8 DIHYDRO 7 (ISOBORNEOL 10 SULFINYL) 5 METHOXY 2 PHENYL[1,2,4]TRIAZOLO[1,2 A]PYRIDAZINE 1,3(2H) DIONE; ALKADIENE; AZAFAGOMINE DERIVATIVE; BENZO[F]CINNOLINE DERIVATIVE; CINNOLINE DERIVATIVE; ENZYME INHIBITOR; GLUCOSIDASE INHIBITOR; NAPHTHALENE DERIVATIVE; PYRIDAZINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CYCLOADDITION; DIELS ALDER REACTION; ENANTIOMER; REACTION ANALYSIS; SUBSTITUTION REACTION; SYNTHESIS;

EID: 2942655292     PISSN: 14246376     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (21)

1. For recent reviews on the application of Diels-Alder cycloadditions: (a) Corey, E. J. Angew. Chem. Int. Ed. 2002, 41, 1650.
2. (b) Nicolau, K. C.; Snyder, S. A.; Montagnon, T.; Vassilikogiannakis, G. Angew. Chem. Int. Ed. 2002, 41, 1668.
3. (a) Aversa, M. C.; Barattucci, A.; Bonaccorsi, P.; Giannetto, P.; Jones, D. N. J. Org. Chem. 1997, 62, 4376.
4. (b) Aversa, M. C.; Barattucci, A.; Bonaccorsi, P.; Giannetto, P.; Nicolò, F. J. Org. Chem. 1999, 64, 2114.
5. (c) Aversa, M. C.; Barattucci, A.; Bonaccorsi, P.; Giannetto, P.; Policicchio, M. J. Org. Chem. 2001, 66, 4845.
6. (d) Aversa, M. C.;. Barattucci, A.;. Bonaccorsi, P.; Bruno, G.; Caruso, F.; Giannetto, P. Tetrahedron: Asymmetry 2001, 12, 2901.
7. (e) Aucagne, V.; Aversa, M. C.; Barattucci, A.; Bonaccorsi, P.; Giannetto, P.; Rollin, P.; Tatibouët, A. J. Org. Chem. 2002, 67, 6925.
8. (f) Aversa, M. C.; Barattucci, A.; Bonaccorsi, P.; Giannetto, P. ARKIVOC 2002, (xi) 79.
9. (g) Aversa, M. C.; Barattucci, A.; Bilardo, M. C.; Bonaccorsi, P.; Giannetto, P. Synthesis 2003, 2241.
10. Cookson, R. C.; Gilani, S. S. H.; Stevens, I. D. R. J. Chem. Soc. C 1967, 1905.
11. Otani, T.; Takayama, J.; Sugihara, Y.; Ishii, A.; Nakayama, J. J. Am Chem. Soc. 2003, 125, 8255.
12. Henderson, A. P.; Mutlu, E.; Leclercq, A.; Bleasdale, C.; Clegg, W.; Henderson, R. A.; Golding, B. T. Chem. Commun. 2002, 1956.
13. (a) Bols, M.; Hazell, R. G.; Thomsen, I. B. Chem. Eur. J. 1997, 3, 940.
14. (b) Ernholt, B. V.; Thomsen, I. B.; Lohse, A.; Plesner, I. W.; Jensen, K. B.; Hazell, R. G.; Liang, X.; Jakobsen, A.; Bols, M. Chem. Eur. J. 2000, 6, 278.
15. (c) Søndergaard, K.; Liang, X.; Bols, M. Chem. Eur. J. 2001, 7, 2324. Jensen, H. H.; Bols, M.J. Chem. Soc., Perkin Trans. 1 2001, 905.
16. (c) Søndergaard, K.; Liang, X.; Bols, M. Chem. Eur. J. 2001, 7, 2324. Jensen, H. H.; Bols, M.J. Chem. Soc., Perkin Trans. 1 2001, 905.
17. Tišler, M.; Stanovnik, B. in Comprehensive Heterocyclic Chemistry, Boulton, A. J.; McKillop, A. Eds., vol. 3, 1984, Pergamon Press, Oxford, pp. 1-56.
18. (a) Barraja, P.; Diana, P.; Lauria, A.; Passannanti, A.; Almerico, A. M. ; Minnei, C.; Longu, S.; Congiu, D.; Musiu, C.; La Colla, P. Bioorg. Med. Chem. 1999, 7, 1591.
19. (b) Stefańska, B.; Arciemiuk, M.; Bontemps-Gracz, M. M., Dzieduszycka, M.; Kupiec, A.; Martelli, S.; Borowski, E. Bioorg. Med. Chem. 2003, 11, 561.
20. Aversa, M. C.; Bonaccorsi, P.; Giannetto, P.; Jafari, S. M. A.; Jones, D. N. Tetrahedron: Asymmetry 1992, 3, 701.
21. Aversa, M. C.; Barattucci, A.; Bonaccorsi, P.; Giannetto, P.; Nicolò, F.; Rizzo, S. Tetrahedron: Asymmetry 1999, 10, 3907.