The solar-chemical photo-Friedel-Crafts heteroacylation of 1,4-quinones

Tetrahedron Letters

Volumn 52, Issue 5, 2011, Pages 609-611

  Benites, Julio ^a   Rios, David ^a   Díaz, Pilar ^a   Valderrama, Jaime A ^a,b  

^a UNIVERSIDAD ARTURO PRAT   (Chile)

^b PONTIFICIA UNIVERSIDAD CATÓLICA DE CHILE   (Chile)

Author keywords

Heteroacylhydroquinones; Heterocycles; Photo Friedel Crafts acylation; Photochemistry; Solar light

Indexed keywords

1,4 BENZO NAPHTHOQUINONE; 1,4 NAPHTHOQUINONE; ALDEHYDE DERIVATIVE; CARBALDEHYDE; HYDROQUINONE DERIVATIVE; UNCLASSIFIED DRUG;

ACYLATION; ARTICLE; DRUG STRUCTURE; FRIEDEL CRAFTS REACTION; PHOTOCHEMISTRY; SOLAR RADIATION;

EID: 78651085633     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.11.149     Document Type: Article

References (43)

1. R.H. Thompson Naturally Occurring Quinones III, Recent Advances 1987 Chapman and Hall London
2. K. Maruyama, and Y. Naruta Chem. Lett. 1977 847 850
3. H. Uno J. Org. Chem. 51 1986 350 358
4. M.A. Brimble, and S.M. Lynds J. Chem. Soc., Perkin Trans. 1 1994 493 496
5. G.A. Kraus, and H. Maeda Tetrahedron Lett. 35 1994 9189
6. P.A. Waske, J. Mattay, and M. Oelgemöller Tetrahedron Lett. 47 2006 1329 1332
7. J.A. Valderrama, D. Pessoa-Mahana, R.A. Tapia, A. Rojas de Arias, H. Nakayama, S. Torres, J. Miret, and M.E. Ferreira Tetrahedron 57 2001 8653 8658
8. J.A. Valderrama, J. Benites, M. Cortés, D. Pessoa-Mahana, E. Prina, and A. Fournet Tetrahedron 58 2002 881 886
9. J.A. Valderrama, C. Zamorano, M.F. González, E. Prina, and A. Fournet Bioorg. Med. Chem. 13 2005 4153 4159
10. J.A. Valderrama, M.F. González, D. Pessoa-Mahana, R.A. Tapia, H. Fillion, F. Pautet, J.A. Rodríguez, C. Theoduloz, and G. Schmeda-Hishmann Bioorg. Med. Chem. 14 2006 5003 5011
11. J.A. Valderrama, M.F. González, P. Colonelli, and D. Vásquez Synlett 2006 2777 2780
12. J.A. Valderrama, and D. Vásquez Tetrahedron Lett. 49 2008 703 706
13. D. Vásquez, J.A. Rodríguez, C. Theoduloz, P. Buc, and J.A. Valderrama Eur. J. Med. Chem. 45 2010 5234 5242
14. H. Naeimi, and L. Moradi Bull. Chem. Soc. Jpn. 78 2005 284 287
15. B.M. Trost, and M.G. Saulnier Tetrahedron Lett. 26 1985 123 126
16. L. Crombie, R.C.F. Jones, and C.J. Palmer Tetrahedron Lett. 26 1985 2933 2936
17. Dorofeenko, G. N.; Tkachenko,V. V. Khim. Geter. Soedin. 1971, 7, 1703; Chem. Abstr. 1971, 76, 153503k.
18. G. Satory, G. Casnati, and F. Bigi J. Org. Chem. 55 1990 4371 4377
19. J.L. Boyer, J.E. Krum, M.C. Myers, A.N. Fazal, and C.T. Wigal J. Org. Chem. 65 2000 4712 4714
20. H. Klinger Justus Liebigs Ann. Chem. 249 1888 137 146
21. H. Klinger, and O. Standke Ber. Dtsch. Chem. Ges. 24 1891 1340 1346
22. H. Klinger, and W. Kolvenbach Ber. Dtsch. Chem. Ges. 31 1898 1214 1216
23. J.M. Bruce S. Patai, The Chemistry of the Quinoid Compounds Vol. 1 1974 John Wiley and Sons New York 503
24. G.A. Kraus, and M. Kirihara J. Org. Chem. 57 1992 3256 3257
25. G.A. Kraus, and P. Liu Tetrahedron Lett. 35 1994 7723 7726
26. K. Kobayashi, M. Suzuki, H. Takeuchi, A. Konishi, H. Sakurai, and H. Suginome J. Chem. Soc., Perkin Trans. 1 1994 1099 1104
27. C. Schiel, M. Oelgemöller, J. Ortner, and J. Mattay Green Chem. 3 2001 224 228
28. M. Oelgemöller, C. Schiel, R. Fröhlich, and J. Mattay Eur. J. Org. Chem. 15 2002 2465 2474
29. M. Oelgemöller, C. Jung, J. Ortner, J. Mattay, C. Schiel, and E. Zimmermann Spectrum 18 2005 28 33
30. B. Murphy, P. Goodrich, C. Christopher Hardacre, and M. Oelgemöller Green Chem. 11 2009 1867 1870
31. G.O. Schenck, and G. Koltzenburg Naturwissenschaften 41 1954 452
32. G.O. Schenck, and G. Koltzenburg Angew. Chem. 66 1954 475
33. R.F. Moore, and W.A. Waters J. Chem. Soc. 1953 238 240
34. J.M. Bruce, and E. Cutts J. Chem. Soc. C 1966 449 458
35. J.M. Bruce, D. Creed, and J.N. Ellis J. Chem. Soc. C 1967 1486 1490
36. J.M. Bruce, and K. Dawes J. Chem. Soc. C 1970 645 648
37. K. Maruyama, and Y. Miyagi Bull. Chem. Soc. Jpn. 47 1974 1303 1304
38. K. Maruyama, H. Sakurai, and T. Otsuki Bull. Chem. Soc. Jpn. 50 1977 2777 2779
39. K. Maruyama, A. Takuwa, S. Matsukiyo, and O. Sogo J. Chem. Soc., Perkin Trans. 1 1980 1414 1419
40. P. Singh, R.T. Pardasani, A. Prasant, C.P. Pokharna, and B. Chaudhary Pharmazie 48 1993 699 700
41. R.T. Pardasani, P. Pardasani, S. Muktawat, R. Ghosh, and T. Mukherjee Heterocycl. Commun. 4 1998 77 80
42. For the mechanism of the benzophenone-initiated photoadditions of acyl radicals to the quinone system see Refs. 23 and 24.
43. 3N: 253.07389; found: 253.07249.