Cascade nucleophilic addition-cyclic Michael addition of arynes and phenols/anilines bearing ortho α,β-unsaturated groups: Facile synthesis of 9-functionalized xanthenes/acridines

Journal of Organic Chemistry

Volumn 75, Issue 2, 2010, Pages 506-509

  Huang, Xian ^a,b   Zhang, Tiexin ^a  

^a ZHEJIANG UNIVERSITY   (China)

^b SHANGHAI INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ACRIDINE DERIVATIVES; BIOCHEMICAL INTERESTS; CHEMICAL EQUATIONS; FACILE SYNTHESIS; FUNCTIONALIZED; MICHAEL ADDITIONS; NUCLEOPHILIC ADDITIONS; ORTHO POSITION;

ADDITION REACTIONS;

SYNTHESIS (CHEMICAL);

9 SPIROXANTHENE DERIVATIVE; ACRIDINE DERIVATIVE; ANILINE DERIVATIVE; PHENOL DERIVATIVE; UNCLASSIFIED DRUG; XANTHENE DERIVATIVE;

ADDITION REACTION; ARTICLE; CHEMICAL STRUCTURE; MICHAEL ADDITION; REACTION ANALYSIS; STRUCTURE ANALYSIS; SYNTHESIS;

ACRIDINES; ALKENES; ANILINE COMPOUNDS; CATALYSIS; CYCLIZATION; MAGNETIC RESONANCE SPECTROSCOPY; MOLECULAR STRUCTURE; PHENOLS; XANTHENES;

EID: 75349090413     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo902311a     Document Type: Article

References (70)

1. (a) Wolff, M. E., Ed. Burger's Medicinal Chemistry, 4th ed.; John Wiley & Sons, Inc.: New York, 1981; Part III, pp 393-407.
2. (b) Smith D. F., Ed. Handbook of Stereoisomer: Drugs in Psychopharmacology; CRC Press; Boca Raton, FL, 1984; pp 255-283.
3. (c) Lednicer, D.; Metscher, L. A. Organic Chemistry of Drug Synthesis; John Wiley & Sons, Inc.: New York, 1977; pp 859-1067.
4. (d) Birman, V. B.; Chopra, A.; Ogle, C. A. Tetrahedron Lett. 1996, 37, 5073.
5. (e) Ajtai, K.; Ilich, P. J. K.; Ringler, A.; Sedarous, S. S.; Toft, D. J.; Burghardt, T. P. Biochemistry 1992, 31, 12431.
6. (a) Okoh, M. P.; Hunter, J. L.; Corrie, J. E. T.; Webb, M. R. Biochemistry 2006, 45, 14764.
7. (b) Ajtai, K.; Burghardt, T. P. Biochemistry 1995, 34, 15943.
8. (c) Salmon-Chemin, L.; Buisine, E.; Yardley, V.; Kohler, S.; Debreu, M.-A.; Landry, V.; Sergheraert, C.; Croft, S. L.; Krauth-Siegel, R. L.; Davioud-Charvet, E. J. Med. Chem. 2001, 44, 548.
9. (d) Blackman, M. J.; Corrie, J. E. T.; Croney, J. C.; Kelly, G.; Eccleston, J. F.; Jameson, D. M. Biochemistry 2002, 41, 12244.
10. (e) Öjemyr, L.; Sandén, T.; Widengren, J.; Brzezinski, P. Biochemistry 2009, 48, 2173.
11. Conibear, P. B.; Jeffreys, D. S.; Seehra, C. K.; Eaton, R. J.; Bagshaw, C. R. Biochemistry 1996, 35, 2299.
12. Gonçalves, M. S. T. Chem. Rev. 2009, 109, 190.
13. (a) Sato, N.; Jitsuoka, M.; Shibata, T.; Hirohashi, T.; Nonoshita, K.; Moriya, M.; Haga, Y.; Sakuraba, A.; Ando, M.; Ohe, T.; Iwaasa, H.; Gomori, A.; Ishihara, A.; Kanatani, A.; Fukami, T. J. Med. Chem. 2008, 51, 4765.
14. (b) Sato, N.; Takahashi, T.; Shibata, T.; Haga, Y.; Sakuraba, A.; Hirose, M.; Sato, M.; Nonoshita, K.; Koike, Y.; Kitazawa, H.; Fujino, N.; Ishii, Y.; Ishihara, A.; Kanatani, A.; Fukami, T. J. Med. Chem. 2003, 46, 666.
15. Naya, A.; Sagara, Y.; Ohwaki, K.; Saeki, T.; Ichikawa, D.; Iwasawa, Y.; Noguchi, K.; Ohtake, N. J. Med. Chem. 2001, 44, 1429.
16. Wischik, C. M.; Edwards, P. C.; Harrington, C. R.; Roth, M.; Klug, A. Inhibition of τ-τ association. U.S. Patent 6 953 794, 2005.
17. Lazarides, T.; McCormick, T.; Du, P.; Luo, G.; Lindley, B.; Eisenberg, R. J. Am. Chem. Soc. 2009, 131, 9192.
18. Yin, J.; Buchwald, S. L. Org. Lett. 2000, 2, 1101.
19. (a) Kuzuya, A.; Mizoguchi, R.; Sasayama, T.; Zhou, J.-M.; Komiyama, M. J. Am. Chem. Soc. 2004, 126, 1430.
20. (b) Carlson, C. B.; Beal, P. A. J. Am. Chem. Soc. 2002, 124, 8510.
21. Bensel, N.; Bahr, N.; Reymond, M. T.; Schenkels, C.; Reymond, J.-L. Helv. Chim. Acta 1999, 82, 44.
22. Fukuzumi, S.; Tokuda, Y.; Etano, T.; Okamoto, T.; Otera, J. J. Am. Chem. Soc. 1993, 115, 8960.
23. (a) Fukuzumi, S.; Okamoto, K.; Tokuda, Y.; Gros, C. P.; Guilard, R. J. Am. Chem. Soc. 2004, 126, 17059.
24. (b) Fukuzumi, S.; Ohkubo, K.; Tokuda, Y.; Suenobu, T. J. Am. Chem. Soc. 2000, 122, 4286.
25. (a) Inhoff, O.; Richards, J. M.; Brîet, J. W.; Lowe, G.; Krauth-Siegel, R. L. J. Med. Chem. 2002, 45, 4524.
26. (b) Bonse, S.; Santelli-Rouvier, C.; Barbe, J.; Krauth-Siegel, R. L. J. Med. Chem. 1999, 42, 5448.
27. (c) Obexer, W.; Schmid, C.; Barbe, J.; Galy, J. P.; Brun, R. Trop. Med. Parasitol. 1995, 46, 49.
28. For construction of xanthene nucleus, see: (a) Ishibashi, H.; Takagaki, K.; Imada, N.; Ikeda, M. Tetrahedron 1994, 50, 10215.
29. (b) Ishibashi, H.; Takagaki, K.; Imada, N.; Ikeda, M. Synlett 1994, 1, 49.
30. For construction of acridine nucleus, see: (c) Baum, J. S.; Condon, M. E.; Shook, D. A. J. Org. Chem. 1987, 52, 2983.
31. (a) Nishino, H.; Kamachi, H.; Baba, H.; Kurosawa, K. J. Org. Chem. 1992, 57, 3551.
32. (b) Prashad, M.; Lu, Y.; Repič, O. J. Org. Chem. 2004, 69, 584.
33. Himeshima, Y.; Sonoda, T.; Kobayashi, H. Chem. Lett. 1983, 1211.
34. Gilchrist, T. L. Supplement C: The Chemistry of Triple Bonded Functional Groups, Part 1; Patai, S., Rappaport, Z., Eds.; John Wiley & Sons: New York, 1983.
35. For reviews on the cascade/tandem reactions of aryne triggered by initial nucleophilic additions, see: (a) Sanz, R. Org. Prep. Proced. Int. 2008, 40, 215.
36. (b) Rathwell, K.; Brimble, M. A. Synthesis 2007, 643.
37. (c) Peña, D.; Pérez, D.; Guitián, E. Angew. Chem., Int. Ed. 2006, 45, 3579.
38. (d) Dyke, A. M.; Hester, A. J.; Lloyd-Jones, G. C. Synthesis 2006, 4093.
39. (e) Pellissier, H.; Santelli, M. Tetrahedron 2003, 59, 701.
40. (f) Biehl, E. R.; Khanapure, S. P. Acc. Chem. Res. 1989, 22, 275.
41. (g) Kessar, S. V. Acc. Chem. Res. 1978, 11, 283.
42. For other cascade/tandem reactions triggered by nucleophilic additions, see: (h) Cant, A. A.; Bertrand, G. H. V.; Henderson, J. L.; Roberts, L.; Greaney, M. F. Angew. Chem., Int. Ed. 2009, 48, 5199.
43. (i) Allan, K. M.; Hong, B. D.; Stoltz, B. M. Org. Biomol. Chem. 2009, 7, 4960.
44. (j) Giacometti, R. D.; Ramtohul, Y. K. Synlett 2009, 2010.
45. (k) Rogness, D. C.; Larock, R. C. Tetrahedron Lett. 2009, 50, 4003.
46. (l) Gilmore, C. D.; Allan, K. M.; Stoltz, B. M. J. Am. Chem. Soc. 2008, 130, 1558.
47. (m) Allan, K. M.; Stoltz, B. M. J. Am. Chem. Soc. 2008, 130, 17270.
48. (n) Soorukram, D.; Qu, T.; Barrett, A. G. M. Org. Lett. 2008, 10, 3833.
49. (o) Blackburn, T.; Ramtohul, Y. K. Synlett 2008, 1159.
50. Okuma, K.; Nojima, A.; Matsunaga, N.; Shioji, K. Org. Lett. 2009, 11, 169.
51. (a) Zhao, J.; Larock, R. C. Org. Lett. 2005, 7, 4273.
52. (b) Zhao, J.; Larock, R. C. J. Org. Chem. 2007, 72, 583.
53. (a) Huang, X.; Xue, J. J. Org. Chem. 2007, 72, 3965.
54. (b) Huang, X.; Zhang, T. Tetrahedron Lett. 2009, 50, 208.
55. (c) Zhang, T.; Huang, X.; Xue, J.; Sun, S. Tetrahedron Lett. 2009, 50, 1290.
56. (d) Sha, F.; Huang, X. Angew. Chem., Int. Ed. 2009, 48, 3458.
57. (e) Xue, J.; Yang, Y.; Huang, X. Synlett 2007, 1533.
58. (f) Xue, J.; Wu, L.; Huang, X. Chin. Chem. Lett. 2008, 19, 631.
59. (g) Xue, J.; Huang, X. Synth. Commun. 2007, 37, 2179.
60. 2, see: (a) Alexakis, A.; Berlan, J.; Besace, Y. Tetrahedron Lett. 1986, 27, 1047.
61. (b) Pollock, P.; Dambacher, J.; Anness, R.; Bergdahl, M. Tetrahedron Lett. 2002, 43, 3693.
62. (c) Li, G.; Wei, H.-X.; Whittlesey, B. R.; Batrice, N. N. J. Org. Chem. 1999, 64, 1061.
63. (a) Morishita, T.; Fukushima, H.; Yoshida, H.; Ohshita, J.; Kunai, A. J. Org. Chem. 2008, 73, 5452.
64. (b) Yoshida, H.; Fukushima, H.; Ohshita, J.; Kunai, A. J. Am. Chem. Soc. 2006, 128, 11040.
65. For existing synthesis of 9-spiro xanthenes, see: (a) Pettit, G. R.; Thomas, E. G.; Herald, C. L. J. Org. Chem. 1981, 46, 4167.
66. (b) Pettit, G. R.; Thomas, E. G. Can. J. Chem. 1982, 60, 629.
67. (c) Pettit, G. R.; Thomas, E. G. Chem. Ind. 1963, 44, 1758.
68. For existing synthesis of 9-spiro acridines, see: (d) Masayuki, F.; Akinori, N.; Masaru, W. Jpn. Kokai Tokkyo Koho JP 2001089457, 2001.
69. For a report of 3a, see: Krohnke, F.; Dickore, K. Chem. Ber. 1959, 92, 46.
70. For a report on the synthesis of 6a, see: Sheppard, C. S.; Levine, R. J. Heterocycl. Chem. 1964, 1, 67.