Photoacylations of 2-substituted 1,4-naphthoquinones: A concise access to biologically active quinonoid compounds

Tetrahedron Letters

Volumn 47, Issue 8, 2006, Pages 1329-1332

  Waske, Prashant A ^a   Mattay, Jochen ^a   Oelgemöller, Michael ^b  

^a BIELEFELD UNIVERSITY   (Germany)

^b DUBLIN CITY UNIVERSITY   (Ireland)

Author keywords

Addition reactions; Aldehydes; Photoacylation; Photochemistry; Quinones

Indexed keywords

ALDEHYDE; BUTYRALDEHYDE; HYDROQUINONE DERIVATIVE; MENADIONE; QUINONE DERIVATIVE;

ACYLATION; ARTICLE; CHEMICAL REACTION; PHOTOCHEMISTRY;

EID: 30944449441     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2005.12.060     Document Type: Article

References (34)

1. S. Patai The Chemistry of the Quinonoid Compounds 1974 John Wiley & Sons New York
2. R.H. Thompson Naturally Occurring Quinones 2nd ed. 1971 Academic Press New York
3. R.A. Morton Biochemistry of Quinones 1965 Academic Press New York
4. M. Oelgemöller, C. Schiel, R. Fröhlich, and J. Mattay Eur. J. Org. Chem. 2002 2465
5. C. Schiel, M. Oelgemöller, and J. Mattay Synthesis 2001 1275
6. C. Schiel, M. Oelgemöller, J. Ortner, and J. Mattay Green Chem. 3 2001 224
7. Oelgemöller, M.; Schiel, C.; Ortner, J.; Mattay, J. In Solare Chemie und solare Materialforschung, AG-Solar NRW, Ed.; 2002; Chapter 2.2., ISBN: 3-89336-306-8 (CD-Rom).
8. For other 'photo Friedel-Crafts' reactions, see: J. Martens, K. Praefcke, and U. Schulze Synthesis 1976 532
9. D. Bryce-Smith, R. Deshpande, A. Gilbert, and J. Grzonka Chem. Commun. 1970 561
10. H. Klinger Justus Liebigs Ann. Chem. 249 1888 137
11. H. Klinger, and O. Standke Ber. Dtsch. Chem. Ges. 24 1891 1340
12. H. Klinger, and W. Kolvenbach Ber. Dtsch. Chem. Ges. 31 1898 1214
13. For a recent review on the photoacylation of quinones, see: M. Oelgemöller, and J. Mattay W.M. Horspool F. Lenci CRC Handbook of Organic Photochemistry and Photobiology 2nd ed. 2004 CRC Press Boca Raton 1 45 Chapter 88
14. For general reviews on the photochemistry of quinones, see: K. Maruyama, and A. Osuka S. Patai Z. Rappoport The Chemistry of Quinonoid Compounds Vol. 2 1988 John Wiley & Sons New York 759 878 Chapter 13
15. J.M. Bruce Quart. Rev. 21 1967 405
16. M.B. Rubin Fortschr. Chem. Forsch. 13 1969 251
17. The reaction of 1 and acetaldehyde gave exclusively 2-methyl-3-acetyl- naphthohydroquinone, although no experimental details were reported: G.O. Schenck, and G. Koltzenburg Naturwiss. 41 1954 452
18. For benzophenone mediated photoacylations of 2-arylamino- and 2-alkylamino 1,4-naphthoquinones, see: K. Kobayashi, M. Suzuki, H. Takeuchi, A. Konishi, H. Sakurai, and H. Suginome J. Chem. Soc., Perkin Trans. 1 1994 1099
19. For Antimalarials based on 1, see: C. Biot, H. Bauer, R.H. Schirmer, and E. Davioud-Charvet J. Med. Chem. 47 2004 5972
20. E. Davioud-Charvet, S. Delarue, C. Biot, B. Schwöbel, C.C. Boehme, A. Müssigbrodt, L. Maes, C. Sergheraert, P. Grellier, R.H. Schirmer, and K. Becker J. Med. Chem. 44 2001 4268
21. For Antimalarials based on 5, see: L.F. Fieser, and H. Heymann J. Biol. Chem. 176 1948 1363
22. L.F. Fieser, E. Berliner, F.J. Bondhus, F.C. Chang, W.G. Dauben, M.G. Ettlinger, G. Fawaz, M. Fields, M. Fieser, C. Heidelberger, H. Heymann, A.M. Seligman, W.R. Vaughan, A.G. Wilson, E. Wilson, M.-I. Wu, M.T. Leffler, K.E. Hamlin, R.J. Hathaway, E.J. Matson, E.E. Moore, M.B. Moore, R.T. Rapala, and H.E. Zaugg J. Am. Chem. Soc. 70 1948 3151 and following papers
23. J. Hase, and T. Nishimura Yakugaku Zasshi-J. Pharm. Soc. Jpn. 75 1955 203
24. J. Hase, and T. Nishimura Yakugaku Zasshi-J. Pharm. Soc. Jpn. 75 1955 207
25. H. Suganuma J. Synth. Org. Chem. Jpn. 59 2001 23
26. Y. Koura, S. Kinoshita, K. Takasuka, S. Koura, N. Osaki, S. Matsumoto, and H. Miyoshi J. Pesticide Sci. 23 1998 18
27. +): 242.09425 (calcd 242.09429).
28. The formation of C- versus O-acylation products was explained on the basis of the nucleophilicity of the acyl radical intermediate and the redox properties of the quinone and the acyl radical: J.M. Bruce, D. Creed, and J.N. Ellis J. Chem. Soc. C 1967 1486
29. A. Takuwa Bull. Chem. Soc. Jpn. 50 1977 2973
30. +): 244.10967 (calcd 244.10994).
31. 5a Further mechanistic investigations are currently carried out for the 2-methyl-1,4-naphthoquinone/butyraldehyde using either thermally or chemically generated acyl radicals.
32. +): 258.08939 (calcd 258.08921).
33. E.A. Couladouros, Z.F. Plyta, and P. Papageorgiou J. Org. Chem. 61 1996 3031
34. M.S. Pearson, B.J. Jensky, F.X. Greer, J.P. Hangstrom, and N.M. Well J. Org. Chem. 43 1978 4617