Synthesis of Azobenzenes from Quinone Acetals and Arylhydrazines

Journal of Organic Chemistry

Volumn 69, Issue 10, 2004, Pages 3413-3416

  Carreño, M Carmen ^a   Mudarra, Gerardo Fernández ^a   Merino, Estíbaliz ^a   Ribagorda, María ^a  

^a UNIVERSIDAD AUTÓNOMA DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CERIUM COMPOUNDS; ISOMERS; KETONES; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

CATALYTIC AMOUNTS; REGIOISOMERS; SUBSTITUENTS;

BENZENE;

4' METHOXY 2 TRIFLUOROMETHYLAZOBENZENE; 4' METHOXY 3' (4 TOLYL)SULFINYL 2,5 DIFLUOROAZOBENZENE; ACETAL DERIVATIVE; AZOBENZENE DERIVATIVE; HYDRAZINE DERIVATIVE; QUINONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS;

EID: 2442693245     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0498011     Document Type: Article

References (66)

1. (a) Zollinger. H. Diazo Chemistry I. Aromatic and Heteroaromatic Compounds; VCH: New York, 1994.
2. (b) Zollinger, H. Color Chemistry: Synthesis, Properties and Applications of Organic Dyes and Pigments; VCH: Weinheim, Germany, 1987.
3. (c) Gordon, P. F.; Gregory, P. Organic Chemistry in Colour; Springer: New York, 1983.
4. (d) The Chemistry of Synthetic Dyes; Venkataraman, K., Ed.; Academic Press: New York, 1970; Vols. 1-7.
5. Behrendt, R.; Renner, C.; Schenk, M.; Wang, F.; Wachtreitl, J.; Oesterhelt, D.; Moroder. L. Angew. Chem., Int. Ed. 1999, 38, 2771 and references therein.
6. Delaire, J. A.; Nakatani. K. Chem. Rev. 2000, 100, 1817-1845.
7. Ikeda, T.; Tsutsumi, O. Science 1995, 268, 1873-1875.
8. Sasaki, T.; Ikeda, T.; Ikimura, K. J. Am. Chem. Soc. 1994, 116, 625-628.
9. (a) Pieraccini, S.; Masiero, S.; Spada, G. P.; Gottarelli, G. Chem. Commun. 2003, 598-599.
10. (b) Liang, X.; Asanuma, H.; Komiyama, M. J. Am. Chem. Soc. 2002, 124, 1877-1883.
11. For comprehensive reviews see: (a) Chem Rev. 2000, 100, 1685-1890 (monographic issue).
12. (b) Molecular Switches; Feringa, B. L., Ed.; Wiley-VCH: Weinheim, Germany, 2001.
13. (c) Willner, I.; Willner, B. In Bioorganic Photochemistry: Biological Applications of Photochemical Switches; Morrison, H., Ed.; Wiley: New York, 1993; Vol. 2, pp 1-110.
14. Murukami, K.; Aoki, M.; Nishi, T.; Ikeda, A.; Shinkai, S. J. Chem. Soc., Chem. Commun. 1991, 1715-1718.
15. Murakami, H.; Kawabuchi, A.; Kotoo, K.; Kutinake, M.; Nakashima, N. J. Am. Chem. Soc. 1997, 119, 7605-7606.
16. Shinkai, S.; Nakaji, T.; Nishida, Y.; Ogawa, T.; Manabe, O. J. Am. Chem. Soc. 1980, 102, 5860-5865.
17. Balzani, V.; Scandola, F. In Supramolecular Photochemistry; Ellis Horwood: Chichester, UK, 1991.
18. (a) Hegarty, A. F. In The Chemistry of Diazonium and Diazo Groups, Part 2; Patai, S., Ed.; Wiley: New York, 1978; pp 545-551.
19. (b) Schündehütte, K. H. In Houben-Weyl, Methoden der organischen Chemie; Stroh, R., Ed.; Thieme: New York, 1965; Bd X/3, S. 226ff.
20. General review of the synthesis of azobenzenes: Szelle, I.; Zollinger, H. Top. Curr. Chem. 1983, 112, 1-66.
21. (a) Barbero, M.; Degani, I.; Dighera, S.; Fochi, R.; Perracino, P. Synthesis 1998, 1235-1237 and references therein.
22. (b) Neumann, W. P.; Wicence, C. Chem. Ber. 1991, 2297-2301.
23. Cohen, T.; Lewarchik, R. J.; Tarino, J. Z. J. Am. Chem. Soc. 1974, 96, 7753-7760.
24. See for instance: (a) Davey, M. H.; Lee, V. Y.; Miller, R. D.; Marks, T. J. J. Org. Chem. 1999, 64, 4976-4979.
25. (b) Boyer, J. H. In The Chemistry of Nitro and Nitroso Groups, Part 2; Feuer, H., Ed.; Interscience: New York, 1961; pp 278-283.
26. (c) Curtin, D. Y.; Tveten, J. L. J. Org. Chem. 1961, 26, 1764-1768.
27. Cox, R. A.; Buncel, E. In The Chemistry of Hydrazo, Azo, and Azoxy Groups; Patai, S., Ed.; Wiley: Chichester, UK, 1975; pp 775-859.
28. For recent examples see: (a) Gowda, S.; Gowda, D. C. Synthesis 2002, 4, 460.
29. (b) Dey Laskar, D.; Projapati, D.; Sandhu, J. S. J. Chem. Soc., Perkin Trans. 1 2000, 67.
30. (c) Wen-hao, W.; Tomohiro, T.; Kodaka, M.; Okumo, H. J. Org. Chem. 2000, 65, 8979.
31. Newbold, B. T. In The Chemistry of Hydrazo, Azo, and Azoxy Groups. Part 1; Patai, S., Ed.; Wiley: Chichester, UK, 1975; pp 543-564.
32. Shine, H. J. In Aromatic Rearrangements; Elsevier: New York, 1967.
33. (a) Kim, K.-Y.; Shin, J.-T.; Lee, K.-S.; Cho, C.-G. Tetrahedron Lett. 2004, 45, 117-120.
34. (b) Lim, Y.-K.; Lee, K.-S.; Cho, C.-G. Org. Lett. 2003, 5, 979-982.
35. Carreño, M. C.; Cuerva, J. M.; Ribagorda, M.; Echavarren, A. M. Angew. Chem., Int. Ed. 1999, 38, 1449-1452.
36. Schmittel, M.; Burghart, A. Angew. Chem., Int. Ed. Engl. 1997, 36, 2551-2589.
37. (a) Nelsen, S.; Pladziewic, J. R. Acc. Chem. Res. 2002, 35, 247-254.
38. (b) Nelsen, S. S.; Ismagilov, R. F.; Gentile, K. E.; Powell, D. R. J. Am. Chem. Soc. 1999, 121, 7108-7114.
39. (a) The Chemistry of Quinonoid Compounds; Rappoport, Z., Patai, S., Eds. ; John Wiley and Sons: New York, 1988; Vol. 2.
40. (b) Thomson, R. H. Naturally Occurring Quinones, Recent Advances; Chapman and Hall: New York; 1987.
41. Borsche, W. Justus Liebigs Ann. Chem. 1908, 357, 171-191.
42. (a) Smith, L. I.; Irwin, W. B.; Guss, C. O. J. Am. Chem. Soc. 1941, 63, 1036-1043.
43. (b) Joshi, S. S.; Deorha, D. S.; Joshi, P. C. J. Indian Chem. Soc. 1961, 39, 395-396.
44. (a) Naemura, K.; Wakebe, T.; Hirase, K.; Tobe, Y. Tetrahedron: Asymmetry 1997, 8, 2585-2595.
45. (b) Naemura, K.; Nishikawa, Y.; Fuji J.; Hirose K.; Tobe, Y. Tetrahedron: Asymmetry 1997, 8, 873-882.
46. (c) Naemura, K.; Takeuchi, S.; Hirose, K.; Tobe, Y.; Kaneda, T.; Sakata, Y. J. Chem. Soc., Perkin Trans. 1 1995, 213-219.
47. (d) Naemura, K.; Takeuchi, S.; Asada, M.; Ueno, K.; Hirose, K.; Tobe, Y. ; Kaneda, T.; Sakata, Y. J. Chem. Soc., Perkin Trans. 1 1995, 1429-1435.
48. (e) Kaneda, T.; Ishizaki; Y.; Misumi, S. J. Am. Chem. Soc. 1988, 110, 2970-2972.
49. (f) Fierz-David, H. E.; Blangey, L.; Streit, H. Helv. Chim. Acta 1946, 29, 1718-1764.
50. (a) Swenton, J. S. In The Chemistry of Quinonoid Compounds; Rappoport, Z., Patai, S., Eds.; John Wiley: New York, 1988; Vol. 2, Part 2, pp 899-962.
51. (b) Swenton, J. S. Acc. Chem. Res. 1983, 16, 74-81.
52. Breuning, M.; Corey, E. J. Org. Lett. 2001, 3, 1559-1562.
53. Imbos, R.; Brilman, M. H.; Pinesche, M.; Feringa, B. L. Org. Lett. 1999, 1, 623-625.
54. Imbos; R.; Minnaard, A. J.; Feringa, B. L. J. Am. Chem. Soc. 2002, 124, 184-185.
55. Dötz, K. H.; Popall, M.; Mueller, G.; Ackermann, K. J. Organomet. Chem. 1990, 383, 93-111.
56. Swenton, J. S.; Anderson, D. K.; Jackson, D. K.; Narasimhan, L. J. Org. Chem. 1981, 46, 4825-4826.
57. Carreño, M. C.; García Ruano, J. L.; Mata, J. M.; Urbano, A. Tetrahedron 1991, 47, 605-614.
58. Henton, D. R.; Anderson, K.; Manning, M. J.; Swenton, J. S. J. Org. Chem. 1980, 45, 3422-3433.
59. 4,4-Dimethoxy-2,5-cyclohexadienone 4: Henton, D. R.; Chenard, B. L.; Swenton, J. S. J. Chem. Soc., Chem. Commun. 1979, 326-327.
60. Zhang, X.-M.; Bordwell, F. G.; Bares, J. E.; Cheng, J. P.; Petrie, B. C. J. Org. Chem. 1993, 58, 3051-3059.
61. Although not isolated, the intermediate formation of an hydrazone had been proposed to explain the replacement of phenolic OH groups by azoaryl substituents in two steps promoted by thallium or lead acetates and followed by acid-catalyzed reaction with arylhydrazines: (a) Taylor, E. C.; Jagdmann, G. E. ; McKillop, A. J. Org. Chem. 1978, 43, 4385-8.
62. (b) Von Hecker, E.; Lattrell, R. Justus Liebigs Ann. Chem. 1963, 662, 48-66.
63. CAN could also act as a Lewis acid, but the easy reaction occurring from 2,4-dinitrophenylhydrazine in the absence of CAN pointed to a different active acidic species.
64. Taylor, R. J. K.; Alcaraz, L.; Kapfer-Eyer, I.; Macdonald, G.; Wei, X.; Lewis, N. Synthesis 1998, 5, 775-790.
65. Compound 14 is also available from the dimethyl acetal of the p-quinol 11.
66. Carreño, M. C.; Pérez González, M.; Fischer, J. Tetrahedron Lett. 1995, 36, 4893-4896.