Pyrimidine and pyrimidone derivatives of [60]fullerene

Tetrahedron Letters

Volumn 38, Issue 14, 1997, Pages 2557-2560

  Tomé, Augusto C ^a   Enes, Roger F ^a   Cavaleiro, José A S ^a   Elguero, José ^b  

^a UNIVERSITY OF AVEIRO   (Portugal)

^b INSTITUTO DE QUÍMICA MÉDICA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

FULLERENE DERIVATIVE; PYRIMIDINE DERIVATIVE; PYRIMIDINONE DERIVATIVE;

ARTICLE; DERIVATIZATION; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS;

EID: 0030986123     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00400-0     Document Type: Article

References (20)

1. a) Hirsch, A. Synthesis, 1995, 895-913;
2. b) Hirsch, A. "The Chemistry of the Fullerenes", Thieme, New York, 1994.
3. For recent reviews on benzo-o-quinodimethanes see: a) Charlton, J.L.; Alauddin, M.M. Tetrahedron, 1987, 43, 2873-2889;
4. b) Martin, N.; Seonae, C.; Hanack, M. Organic Prep. and Procedures Int., 1991, 23, 237-272.
5. For recent reviews on heteroaromatic o-quinodimethanes see: a) Chou, T.-S. Reviews on Heteroatom Chem., 1993, 8, 65-104;
6. b) Ando, K.; Takayama, H. Heterocycles, 1994, 37, 1417-1439.
7. a) Fernández-Paniagua, U.M.; Illescas, B.M.; Martín, N.; Seoane, C. J. Chem. Soc., Perkin Trans. 1, 1996, 1077-1079;
8. b) Eguchi, S.; Ohno, M.; Kojima, S.; Koide, N.; Yashiro, A.; Shirakawa, Y.; Ishida, H. Fullerene Sci. Technol., 1996, 4, 303-327.
9. a) Tomé, A.C.; Cavaleiro, J.A.S.; Storr, R.C. Tetrahedron, 1996, 52, 1735-1746;
10. b) Tomé, A.C.; Cavaleiro, J.A.S.; Storr, R.C. Tetrahedron Lett., 1993, 34, 6639-6642.
11. a) Tomé, A.C.; Cavaleiro, J.A.S.; Storr, R.C. Tetrahedron, 1996, 52, 1723-1734;
12. b) Tomé, A.C.; O'Neill, P.M.; Cavaleiro, J.A.S.; Storr, R.C. Synlett, 1993, 347-348.
13. 60 were eluted with toluene and the adduct was then eluted with chloroform.
14. 60] = 720.
15. +) m/z (rel.int.) 330 (M+, 4%), 262 (60), 224 (13), 211 (27), 210 (30), 198 (36), 181 (18), 104 (100), 85 (19), 77 (35), 69 (29).
16. 3 carbons. This means that the four carbon atoms of the piperazinyl group are not magnetically equivalent. This effect (not observed in sulfone 5b lacking the acetyl group) is probably due to the restricted rotation of the acetyl group about the C-N bond (a phenomenon common to N,N'-disubstituted amides) .
17. Stothers, J.B. "Carbon-13 NMR Spectroscopy", Academic Press, New York, 1972, pag. 427.
18. 60 with 7b the adduct 8b was accompaigned by a minor fraction corresponding to 2:1 adducts (two pyrimodone o-quinodimethanes added to one fullerene molecule), as indicated by its mass spectrum.
19. max (KBr) 2360, 2341, 1666, 1540, 1428, 669, 526.
20. Nakamura E., Tokuyama H., Yamago S., Shiraki T., Sugiura Y. Bull. Chem. Soc. Japan. 69:1996;2143-2151. and references cited therein.