Novel quinone-fused corroles

Tetrahedron Letters

Volumn 48, Issue 50, 2007, Pages 8904-8908

  Vale, Luís S H P ^a   Barata, Joana F B ^a   Neves, Maria G P M S ^a   Faustino, Maria A F ^a   Tomé, Augusto C ^a   Silva, Artur M S ^a   Paz, Filipe A A ^b   Cavaleiro, José A S ^a  

^a UNIVERSITY OF AVEIRO   (Portugal)

^b UNIVERSITY OF AVEIRO   (Portugal)

Author keywords

1,3 Dipolar cycloadditions; Azomethine ylides; Corroles; Quinones

Indexed keywords

5,10,15 TRIS(PENTAFLUOROPHENYL)CORROLE 3 CARBALDEHYDE; AZOMETHINE YLIDE; GALLIUM; PYRIDINE DERIVATIVE; QUINONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL BOND; CRYSTAL STRUCTURE; CYCLOADDITION; DEHYDROGENATION;

EID: 36049007224     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.10.054     Document Type: Article

References (42)

1. Gross Z., Galili N., and Saltsman I. Angew. Chem., Int. Ed. 38 (1999) 1427-1429
2. Paolesse R., Nardis S., Sagone F., and Khoury R.G. J. Org. Chem. 66 (2001) 550-556
3. Gryko D.T. Eur. J. Org. Chem. (2002) 1735-1743
4. Gryko D.T., and Koszarna B. Org. Biomol. Chem. 1 (2003) 350-357
5. Nardis S., Monti D., and Paolesse R. Mini-Rev. Org. Chem. (2005) 355-374
6. A recent review:. Aviv I., and Gross Z. Chem. Commun. (2007) 1987-1999
7. Gross Z., and Gray H.B. Adv. Synth. Catal. 346 (2004) 165-170
8. Barbe J.M., Canard G., Brandès S., and Guilard R. Angew. Chem., Int. Ed. 44 (2005) 3103-3106
9. Barbe J.M., Canard G., Brandès S., and Guilard R. Chem. Eur. J. 13 (2007) 2118-2129
10. Walker D., Chappel S., Mahammed A., Brunschwig B.S., Winkler J.R., Gray H.B., Zaban A., and Gross Z. J. Porphryins Phthalocyanines 10 (2006) 1259-1262
11. Fu, B.; Huang, J.; Ren, L.; Weng, X.; Zhou, Y.; Du, Y.; Wu, X.; Zhou, X.; Yang, G. Chem. Commun. 2007, 3264-3266.
12. Gershman Z., Goldberg I., and Gross Z. Angew. Chem., Int. Ed. 46 (2007) 4320-4324
13. Bendix J., Dmochowski I.J., Gray H.B., Mahammed A., Simkhovich L., and Gross Z. Angew. Chem., Int. Ed. 39 (2000) 4048-4051
14. Mahammed A., Goldberg I., and Gross Z. Org. Lett. 3 (2001) 3443-3446
15. Saltsman I., Mahammed A., Goldberg I., Tkachenko E., Botoshansky M., and Gross Z. J. Am. Chem. Soc. 124 (2002) 7411-7420
16. Paolesse R., Nardis S., Venanzi M., Mastroianni M., Russo M., Fronczek F.R., and Vicente M.G.H. Chem. Eur. J. 9 (2003) 1192-1197
17. Hiroto S., Hisaki I., Shinokubo H., and Osuka A. Angew. Chem., Int. Ed. 44 (2005) 6763-6766
18. Maes W., Ngo T.H., Vanderhaeghen J., and Dehaen W. Org. Lett. 9 (2007) 3165-3168
19. Tomé A.C., Lacerda P.S.S., Neves M.G.P.M.S., and Cavaleiro J.A.S. Chem. Commun. (1997) 1199-1200
20. Silva A.M.G., Tomé A.C., Neves M.G.P.M.S., and Cavaleiro J.A.S. Tetrahedron Lett. 41 (2000) 3065-3068
21. Silva A.M.G., Tomé A.C., Neves M.G.P.M.S., Cavaleiro J.A.S., and Kappe C.O. Tetrahedron Lett. 46 (2005) 4723-4726
22. Silva A.M.G., Tomé A.C., Neves M.G.P.M.S., Silva A.M.S., and Cavaleiro J.A.S. Chem. Commun. (1999) 1767-1768
23. Silva A.M.G., Tomé A.C., Neves M.G.P.M.S., Silva A.M.S., and Cavaleiro J.A.S. J. Org. Chem. 67 (2002) 726-732
24. Silva A.M.G., Tomé A.C., Neves M.G.P.M.S., Silva A.M.S., Cavaleiro J.A.S., Perrone D., and Dondoni A. Tetrahedron Lett. 43 (2002) 603-605
25. Silva A.M.G., Tomé A.C., Neves M.G.P.M.S., Cavaleiro J.A.S., Perrone D., and Dondoni A. Synlett (2005) 857-859
26. Silva A.M.G., Tomé A.C., Neves M.G.P.M.S., Silva A.M.S., and Cavaleiro J.A.S. J. Org. Chem. 70 (2005) 2306-2314
27. Silva A.M.G., Lacerda P.S.S., Tomé A.C., Neves M.G.P.M.S., Silva A.M.S., Cavaleiro J.A.S., Makarova E.A., and Lukyanets E.A. J. Org. Chem. 71 (2006) 8352-8356
28. Barata J.F.B., Silva A.M.G., Faustino M.A.F., Neves M.G.P.M.S., Tome A.C., Silva A.M.S., and Cavaleiro J.A.S. Synlett (2004) 1291-1293
29. 7d
30. 2/hexane/pyridine (a few drops).
31. 5N. The coordinated pyridine is thus exchanged by a deuterated pyridine.
32. + calcd 1022.0158, found 1022.0192.
33. + calcd 1072.0315, found 1072.0307.
34. {radical dot}+ calcd 1041.9971, found 1041.9935.
35. Cava M.P., Deana A., and Mut K. J. Am. Chem. Soc. 81 (1959) 6458-6460
36. + calcd 1122.0471, found 1122.0500.
37. + calcd 1093.0206, found 1093.0241.
38. 2 = 0.4671 (all data). Data completeness to theta = 25.35°, 88.3%. Crystallographic data (excluding structure factors) for the structure reported in this Letter have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication no. CCDC-654082. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 2EZ, UK. Fax: +44 1223 336033. E-mail: deposit@ccdc.cam.ac.uk.
39. Allen F.H. Acta Crystallogr. B 58 (2002) 380-388
40. Allen F.H., and Motherwell W.D.S. Acta Crystallogr. B 58 (2002) 407-422
41. Silva A.M.G., Faustino M.A.F., Tomé A.C., Neves M.G.P.M.S., Silva A.M.S., and Cavaleiro J.A.S. J. Chem. Soc., Perkin Trans. 1 (2001) 2752-2753
42. Vicente M.G.H., Jaquinod L., Khoury R.G., Madrona A.Y., and Smith K.M. Tetrahedron Lett. 40 (1999) 8763-8766