Pyrimidine ortho-quinodimethanes. Part 2: Synthesis of new [60]fullerene adducts based on substituted pyrimidine derivatives and their 1H NMR dynamic study

Tetrahedron

Volumn 65, Issue 29-30, 2009, Pages 5817-5823

  Herrera, Antonio ^a   Martínez Alvarez, Roberto ^a   Martín, Nazario ^a   Chioua, Mourad ^a   Chioua, Rachid ^a   Molero, Dolores ^b   Sánchez Vázquez, Angel ^b   Almy, John ^c  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

^b Facultad de Química   (Spain)

^c CALIFORNIA STATE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1',2',3',4' TETRAHYDRO 6' METHYLSULFONYL 8' AMINOQUINAZOLINO[2',3':1,2][6']FULLERENE; 1',2',3',4' TETRAHYDRO 6',8' BIS(METHYLSULFANYL)QUINAZOLINO[2',3':1,2][6']FULLERENE; 1',2',3',4' TETRAHYDRO 6',8' BIS(METHYLSULFONYL)QUINAZOLINO [2',3':1,2][6']FULLERENE; 1',2',3',4' TETRAHYDRO 6',8' DIMETHOXYQUINAZOLINO [2',3':1,2][6']FULLERENE; 1',2',3',4' TETRAHYDROQUINAZOLINO[2',3':1,2][6']FULLERENE 6',8' (5H 7H) DIONE; 2,4 BIS(METHYLSULFANYL) 5,6 DIHYDROCYCLOBUTA[D]PYRIMIDINE; 2,4 BIS(METHYLSULFONYL) 5,6 DIHYDROCYCLOBUTA[D]PYRIMIDINE; 2,4 DIMETHOXY 5,6 DIHYDROCYCLOBUTA[D]PYRIMIDINE; 4 AMINO 2 (METHYLSULFONYL) 5,6 DIHYDROCYCLOBUTA[D]PYRIMIDINE; FULLERENE DERIVATIVE; PYRIMIDINE DERIVATIVE; QUINAZOLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; DIELS ALDER REACTION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; TEMPERATURE MEASUREMENT; THERMODYNAMICS;

ALNUS;

EID: 66949126053     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2009.05.026     Document Type: Article

References (55)

1. In: Guldi D.M., and Martín N. (Eds). Fullerenes: From Synthesis to Optoelectronic Properties (2002), Kluwer Academic, Dordrech, The Netherlands
2. Hirsch A., and Brettreich M. The Chemistry of Fullerenes (2005), Wiley-VCH, Weinheim, Germany
3. Fullerenes. Principles and Applications. In: Langa de la Puente F., and Nierengarten J.-F. (Eds). RSC Nanoscience and Nanotechnology Series (2007), RSC, Cambridge, United Kingdom
4. Signorini R., Meneghetti M., Bozio R., Maggini M., Scorrano G., Prato M., Brusatin G., Innocenzi P., and Guglielmi M. Carbon 38 (2000) 1653-1662
5. Kondoumas E., Konstantaki M., Mavromanolakis A., Couris S., Fanti M., Zerbetto F., Kordatos K., and Prato M. Chem.-Eur. J. 9 (2003) 1529-1534
6. Xenogiannopoulou E., Mevded M., Iliopoulos K., Couris S., Papadopoulos M.G., Bonifazi D., Sooambar C., Mateo-Alonso A., and Prato M. Chem. Phys. Chem. 8 (2007) 1056-1064
7. Mateo-Alonso A., Iliopoulos K., Ocurrís S., and Prato M. J. Am. Chem. Soc. 130 (2008) 1534-1535
8. Mateo-Alonso A., Ehil C., Aminur Rahman G.M., Guldi D.M., Fiovaranti G., Marcaccio M., Paolucci F., and Prato M. Angew. Chem., Int. Ed. 46 (2007) 3521-3525
9. Mateo-Alonso A., Guldi D.M., Paolucci F., and Prato M. Angew. Chem., Int. Ed. 46 (2007) 8120-8126
10. As representative examples, see:
11. Guldi D.M., and Prato M. J. Am. Chem. Soc. 119 (1997) 974-980
12. Martín N., Sánchez L., Herranz M.A., Illescas B., and Guldi D.M. Acc. Chem. Res. 40 (2007) 1015-1024
13. Pérez E.M., Sánchez L., Fernández G., and Martín N. J. Am. Chem. Soc. 128 (2006) 7172-7173
14. Ma W., Yang C., Gong X., Lee K., and Heeger A.J. Adv. Funct. Mater. 15 (2005) 1617-1622
15. Li G., Shrotriya S., Huang J., Yao Y., Moriarty T., Emery K., and Yang Y. Nat. Mater. 4 (2005) 864-868
16. Riedel I., von Hauff E., Parisi J., Martín N., Giacalone F., and Dyakonov V. Adv. Funct. Mater. 15 (2005) 1979-1987
17. Kim J.K., Lee K., Coates N.E., Moses D., Nguyen T.-Q., Dante M., and Heeger A.J. Nature 317 (2007) 222-225
18. For a recent review, see:. Thompson B.C., and Fréchet J.M.J. Angew. Chem., Int. Ed. 47 (2008) 58-77
19. Amriou S., Mehta A., and Bryce M.R. J. Mater. Chem. 15 (2005) 1232-1234
20. For a review, see:. Sánchez L., Martín N., and Guldi D.M. Angew. Chem., Int. Ed. 44 (2005) 5374-5382
21. For reviews, see:
22. Pérez E.M., and Martín N. Chem. Soc. Rev. 37 (2008) 1512-1519
23. Guldi D.M., and Martín M. J. Mater. Chem. 12 (2002) 1978-1992
24. Maggini M., Scorrano G., and Prato M. J. Am. Chem. Soc. 115 (1993) 9798-9799
25. Prato M., and Maggini M. Acc. Chem. Res. 31 (1998) 519-526
26. Segura J.L., and Martín N. Chem. Rev. 99 (1999) 3199-3246
27. Fernández-Paniagua U.M., Illescas B., Martín N., Seoane C., de la Cruz P., de la Hoz A., and Langa F. J. Org. Chem. 62 (1997) 3705-3710
28. Liu J.-H., Wu A.-T., Huang M.-H., Wu C.-W., and Cheng W.-S. J. Org. Chem. 65 (2000) 3395-3403
29. Tomé A.C., Ener R.F., Cavaleiro J.A.S., and Elguero J. Tetrahedron Lett. 38 (1997) 2557-2560
30. Tomé A.C., Enes R.F., Tomé J.P.C., Rocha J., Neves M.G.P.M.S., Cavaleiro J.A.S., and Elguero J. Tetrahedron 54 (1998) 11141-11150
31. Enes R.F., Tomé A.C., and Cavaleiro J.A.S. Tetrahedron 61 (2005) 1423-1431
32. Hermann A., Diederich F., Thilgen C., ter Meer H.-U., and Müller W.H. Helv. Chim. Acta 77 (1994) 1689-1706
33. García Martínez A., Herrera Fernández A., Moreno Jiménez F., García Fraile A., Subramanian L.R., and Hanack M. J. Org. Chem. 57 (1992) 1627-1630
34. García Martínez A., Herrera A., Moreno F., Luengo M.J., and Subramanian L.R. Synlett (1994) 559-560
35. Herrera A., Martínez-Alvarez R., Martín N., Chioua M., Chioua R., Sánchez-Vazquez A., Molero D., and Almy J. Tetrahedron 65 (2009) 1697-1703
36. Herrera A., Martínez R., Gónzalez B., Illescas B., Martín N., and Seoane C. Tetrahedron Lett. 27 (1997) 4873-4876
37. González B., Herrera A., Illescas B., Martín N., Martínez R., Moreno F., Sánchez L., and Sánchez A. J. Org. Chem. 63 (1998) 6807-6813
38. Nakamura Y., O-Kawa K., Minami S., Ogawa T., Tobita S., and Nishimura J. J. Org. Chem. 67 (2002) 1247-1252
39. Sandström J. Dynamic NMR Spectroscopy (1982), Academic, London p 96
40. Nakamura Y., Minowa T., Tobita S., Shizuka H., and Nishimura J. J. Chem. Soc., Perkin Trans. 2 (1995) 2351-2357
41. Darwish A.D., Avent A.G., Birkett P.R., Kroto H.W., Taylor R., and Waltom D.R.M. J. Chem. Soc., Perkin Trans. 2 (2001) 1038-1044 and references therein
42. Rondeau D., Kreher D., Cariou M., Hudhomme P., Gorgues A., and Richomme P. Rapid Commun. Mass Spectrom. 15 (2001) 1708-1712
43. Rondeau D., Martineau C., Blanchard P., and Roncali J. J. Mass Spectrom. 10 (2002) 1081-1085
44. Kozlovski V., Brusov I., Sulimenkov A., Pikhtelev A., and Dodonov A. Rapid Commun. Mass Spectrom. 18 (2004) 780-786
45. Marchesan S., Da Ros T., and Prato M. J. Org. Chem. 70 (2005) 4706-4713
46. Martín N., Altable M., Fillipone S., Martín-Domenech A., Echegoyen L., and Cardona C.M. Angew. Chem., Int. Ed. 45 (2006) 110-114
47. Lukoyanova O., Cardona C.M., Altable M., Fillipone S., Martín-Domenech A., Martín N., and Echegoyen L. Angew. Chem., Int. Ed. 45 (2006) 7430-7433
48. Turecek F., and Hanus V. Mass Spectrom. Rev. 3 (1984) 85-152
49. Szmigielski R., Danikiewicz W., Dolatowska K., and Wojciechowski K. Int. J. Mass Spectrom. 248 (2006) 148-154
50. Meurer E.C., Sparrapan R., and Eberlin M.N. J. Mass Spectrom. 38 (2003) 1075-1080
51. Ovcharenko V.V., Pihlaja K., and Stajer G. J. Am. Soc. Mass Spectrom. 12 (2001) 1011-1019
52. Martín N., Altable M., Filippone S., Martín-Domenech A., Martínez-Alvarez R., Suárez M., Plonska-Brzezinska M.E., Lukoyanova O., and Echegoyen L. J. Org. Chem. 72 (2007) 3840-3846
53. Martínez R., Herrera A., Martín N., González B., and Illescas B. Rapid Commun. Mass Spectrom. 12 (1998) 568-570
54. Stang P.J., Hanack M., and Subramanian L.R. Synthesis (1982) 85-126
55. Stang P.J., and Dueber T.E. Org. Synth. 54 (1974) 79-80