Studies on the chemistry of 2-(2-oxo-3-phenylpropyl)-benzaldehydes: Novel total synthesis of 3-phenylnaphthalen-2-ols and 2-hydroxy-3-phenyl-1,4- naphthoquinones

Tetrahedron

Volumn 61, Issue 2, 2005, Pages 485-492

  Martínez, Ana ^a   Fernández, Marcos ^a   Estévez, Juan C ^a   Estévez, Ramón J ^a   Castedo, Luis ^a  

^a UNIVERSITY OF SANTIAGO DE COMPOSTELA   (Spain)

Author keywords

Aldol reaction; Cyclization; Oxidation; Quinones

Indexed keywords

1,2 NAPHTHOQUINONE DERIVATIVE; 1,4 NAPHTHOQUINONE DERIVATIVE; 2 HYDROXY 3 PHENYL[1,4]NAPHTHOQUINONE; 2 HYDROXY 7 METHOXY 3 PHENYL[1,4]NAPHTHOQUINONE; 3 PHENYL 1,2 NAPHTHOQUINONE; 7 METHOXY 3 PHENYL[1,2]NAPHTHOQUINONE; BENZALDEHYDE DERIVATIVE; QUINONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; DRUG SYNTHESIS; OXIDATION; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 9744267495     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.10.043     Document Type: Article

References (62)

1. S. Patai Z. Rappoport The Chemistry of the Quinoid Compounds 1988 Wiley-Interscience New York
2. M. Tisler A.R. Katritzky Heterocyclic Quinones Advances in Heterocyclic Chemistry Vol. 45 1989 Academic London 37
3. R.H. Thomson Naturally Occurring Quinones 4th ed. 1997 Chapman & Hall London
4. For a recent review, see: S. Spyroudis Molecules 5 2002 1291
5. A.R. Mehendale, and R.H. Thomson Binaphthoquinones in Lomatia ferruginea Phytochemistry 14 1975 801 802
6. J.C. Barcia, J. Cruces, J.C. Estevez, R.J. Estevez, and L. Castedo Tetrahedron Lett. 43 2002 5141
7. J. Yin, and L.S. Liebeskind J. Org. Chem. 63 1998 5726 5727
8. N.E. Mackenzie, S. Surendrakumar, R.H. Thomson, H.J. Cowe, and P.J. Cox J. Chem. Soc., Perkin Trans. 1 1986 2233
9. A. Emadi, J.S. Harwood, S. Kohanim, and K.W. Stagliano Org. Lett. 4 2002 521
10. K. Krohn, H. Rieger, and K. Khanbabaee Chem. Ber. 122 1989 2323
11. D.H.R. Barton, J.P. Finet, and M. Thomas Tetrahedron 44 1988 6397
12. D. Murali, and G.S.K. Rao Indian J. Chem., Sect. B 26B 1987 668
13. H.s.J. Duchstein Arch. Pharm. 320 1987 460
14. H. Laatsch Liebigs Ann. Chem. 1985 1847
15. D.H.R. Barton, A.G. Brewster, S.V. Ley, C.M. Read, and M.N. Rosenfeld J. Chem. Soc., Perkin Trans. 1 1981 1473
16. K.B. Sukumaran, and R.G.B. Harvey J. Org. Chem. 45 1980 4407
17. H. Ishii, T. Hanaoka, T. Asaka, Y. Harada, and N. Ikeda Tetrahedron 32 1976 2693
18. S.M.S. Chauhan, B. Kalra, and P.P. Mohapatra J. Mol. Catal. 137 1999 85
19. S. Suresh, S. Skaria, and S. Ponrathnam Synth. Commun. 26 1996 2113
20. K. Krohn, H. Rieger, and K. Brueggmann Synthesis 1990 1141
21. J. Suzuki, T. Watanabe, and S. Suzuki Chem. Pharm. Bull. 36 1988 2204
22. M. Lemaire, A. Guy, J. Roussel, and J.P. Guette Tetrahedron 43 1987 835
23. A.V. Pinto, V.F. Ferreira, and M.C.F.R. Pinto Synth. Commun. 15 1985 1177
24. H. Arzeno, D.H.R. Barton, R.M. Berge-Lurion, X. Lusinchi, and B.M. Pinto J. Chem. Soc., Perkin Trans. 1 1984 2069
25. L. Horner, and K.H. Weber Chem. Ber. 1965 1246
26. For recent examples on the oxidation of naphthols to naphthoquinones, see: (a) X. Chen, J.S. Zhang, and M. Zhao Chin. Chem. Lett. 12 2001 297
27. J.K. Ray, S. Gupta, G.K. Kar, B.C. Roy, J.-M. Lin, and S. Amin J. Org. Chem. 65 2000 8134
28. S. Kumar, and T.-Y. Kim J. Org. Chem. 65 2000 3883
29. E.A. Couladouros, and A.T. Strongilos Tetrahedron Lett. 41 2000 535
30. J.H. Buttery, and D. Wege Aust. J. Chem. 51 1998 409
31. G. Majetich, S. Liu, J. Fang, D. Siesel, and Y. Zhang J. Org. Chem. 62 1997 6928
32. S. Croux, M.-T. Maurette, M. Hocquaux, A. Ananides, A.M. Braun, and E. Oliveros New J. Chem. 14 1990 161 167
33. D.M. Min, S. Croux, C. Tournair, M. Hocquaux, B. Jacquet, E. Oliveros, and M.-T. Maurette Tetrahedron 48 1990 1869 1882
34. A. Bekaert, J. Andrieux, M. Plat, and J.-D. Brion Tetrahedron Lett. 38 1997 4219 4220
35. B.H. Lipshutz, and Y.-J. Shin Tetrahedron Lett. 39 1998 7017
36. A.N. Kost, V.I. Terenin, L.G. Yudin, and R.S. Sagitullin Khim. Geterotsiklich. Soedin. 1980 1272
37. D.L. Fields J. Org. Chem. 36 1971 3002
38. For previous, low yielding methods for the synthesis of 3-phenyl-1,2-naphthoquinones, see: (a) N.E. Mackenzie, S. Surendrakumar, R.H. Thomson, H.J. Cowe, and P.J. Cox J. Chem. Soc., Perkin Trans. 1 1986 2233
39. J. Asselin, P. Brassard, and P. L'Ecuyer Can. J. Chem. 44 1966 2563
40. E. Martinez, L. Martinez, M. Treus, J.C. Estevez, R.J. Estevez, and L. Castedo Tetrahedron 56 2000 6023
41. E. Martínez, L. Martínez, J.C. Estévez, R.J. Estévez, and L. Castedo Tetrahedron Lett. 39 1998 2175 2176
42. C.C. Cheng, Q. Dong, D.F. Liu, Y.L. Luo, L.F. Liu, A.Y. Chen, C. Yu, N. Savaraj, and T.C. Chou J. Med. Chem. 36 1993 4108
43. C. Gabaja, E.M. Perchelet, J.-P. Perchellet, and G.B. Jones Tetrahedron Lett. 41 2000 3007 3010
44. G. Qabaja, and G.B. Jones J. Org. Chem. 65 2000 7187
45. A.M. Echavarren, N. Tamayo, and D.J. Cardenas J. Org. Chem. 59 1994 6075
46. M. Watanabe, M. Date, and S. Furukawa Chem. Pharm. Bull. 37 1989 292
47. K. Kobayashi, T. Taki, M. Kawakita, M. Uchida, O. Morikawa, and H. Konishi Heterocycles 51 1999 349 354
48. A.M. Echavarren, N. Tamayo, O. De Frutos, and A. Garcia Tetrahedron 53 1997 16835
49. J.C. Estevez, R.J. Estevez, and L. Castedo Tetrahedron Lett. 34 1993 6479
50. A. Martínez, J.C. Estévez, R.J. Estévez, and L. Castedo Tetrahedron Lett. 41 2000 2365 2367
51. For a previous lower yielding preparation of benzylydeneindanone 8a, see: S. Titouani, M. Soufiaoui, L. Toupet, and R. Carrie Tetrahedron 46 1990 3869
52. For a lower yielding preparation of 8a in acidic conditions, see: C. Berthelette, C. McCooye, Y. Leblanc, L.A. Trimble, and N.N. Tsou J. Org. Chem. 62 1997 4339
53. D. Basavaiah, and R.M. Reddy Tetrahedron Lett. 42 2001 3025
54. J.H. Buttery, and D. Wege Aust. J. Chem. 51 1998 409
55. A. Chatterjee, L.N. Dutta, and S.K. Chatterjee Indian J. Chem., Sect. B 19B 1980 955
56. N. Campbell, P.S. Davison, and H.G. Heller J. Chem. Soc. 1963 993
57. K.-Y. Ko, and E.L. Eliel J. Org. Chem. 1986 5353
58. R. Rangarajan, and E.J. Eisenbraun J. Org. Chem. 50 1985 2435
59. For a previous less efficient synthesis of ketoacid 12a, see: J. Schnekenburger Arch. Pharm. 279 1964 734
60. N.H. Rama, R. Iqbal, K. Zamani, and A. Malik Indian J. Chem., Sect. B 37B 1998 1021
61. S.C. Tewari, S.N. Rastogi, and N. Anand Indian J. Chem., Sect. B 19B 1980 139
62. D.D. Perrin, and W.L.F. Armarego Purification of Laboratory Chemicals 1988 Pergamon New York