Preparation of polyfunctional aryl azides from aryl triazenes. A new synthesis of ellipticine, 9-methoxyellipticine, isoellipticine, and 7-carbethoxyisoellipticine

Journal of Organic Chemistry

Volumn 72, Issue 19, 2007, Pages 7106-7115

  Liu, Ching Yuan ^a   Knochel, Paul ^a  

^a UNIVERSITY OF MUNICH   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

BORONIC ESTERS; CARBETHOXYISOELLIPTICINE; POLYFUNCTIONAL ARYL AZIDES;

ESTERS; KETONES; MOLECULAR STRUCTURE; ONCOLOGY; REACTION KINETICS; SYNTHESIS (CHEMICAL);

AMINES;

7 CARBETHOXYISOELLIPTICINE; 9 METHOXYELLIPTICINE; ALDEHYDE DERIVATIVE; AZIDE; BORON DERIVATIVE; ELLIPTICINE; ESTER DERIVATIVE; HALIDE; ISOELLIPTICINE; KETONE DERIVATIVE; NITRILE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; SODIUM AZIDE; TRIAZENE DERIVATIVE; TRIFLUOROACETIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; DECOMPOSITION; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 34548749746     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo070774z     Document Type: Article

References (65)

1. (a) Bräse, S.; Gil, C.; Knepper, K.; Zimmermann, V. Angew. Chem. 2005, 117, 5320;
2. Angew. Chem., Int. Ed. 2005, 44, 5188;.
3. (b) Patai, S. The Chemistry of Diazonium and Diazo Groups. In The Chemistry of Functional Groups; Patai, S., Ed.; John Wiley: Chichester, UK, 1978.
4. Kumar, H. M. S.; Reddy, B. V. S.; Anjaneyulu, S.; Jadav, J. S. Tetrahedron Lett. 1999, 40, 8305.
5. (a) Huisgen, R. Angew. Chem. 1963, 75, 604;
6. Angew. Chem., Int. Ed. 1963, 2, 565.
7. (b) Huisgen, R.; Knorr, R.; Mobius, L.; Szeimies, G. Chem. Ber. 1965, 98, 4014.
8. (a) Tiemann, F. Ber. Dtsch. Chem. Ges. 1891, 24, 4162.
9. (b) Gritsan, N. P.; Pritchina, E. A. Russ. Chem. Rev. 1992, 61, 500.
10. (c) Budyka, M. F.; Kantor, M. M.; Alfimov, M. V. Russ. Chem. Rev. 1992, 61, 25.
11. Bucher, G. In CRC Handbook of Organic Photochemistry and Photobiology; CRC: Boca Raton, FL, 2004; S. 44/1-44/31.
12. Bräse, S.; Gil, C.; knepper, K.; Zimmermann, V. Synlett 2004, 1163.
13. (a) Krasovskiy, A.; Knochel, P. Angew. Chem., Int. Ed. 2004, 43, 3333.
14. (b) Kopp, F.; Krasovskiy, A.; Knochel, P. Chem. Commun. 2004, 2288.
15. (c) Ren, H.; Krasovskiy, A.; Knochel, P. Org. Lett. 2004, 6, 4215.
16. (d) Ren, H.; Krasovskiy, A.; Knochel, P. Chem. Commun. 2005, 543.
17. (e) Kopp, F.; Sklute, G.; Polborn, K.; Marek, J.; Knochel, P. Org. Lett. 2005, 7, 3789.
18. (f) Liu, C. Y.; Ren, H.; Knochel, P. Org. Lett. 2006, 8, 617.
19. See also: (g) Knochel, P.; Dohle, W.; Gommermann, N.; Kneisel, F. F.; Kopp, F.; Korn, T.; Sapountzis, I.; Vu, V. A. Angew. Chem., Int. Ed. 2003, 42, 4302.
20. (h) Liu, C. Y.; Knochel, P. Org. Lett. 2005, 7, 2543.
21. (a) Wallach, O. Liebigs Ann. Chem. 1886, 235, 233.
22. (b) Wallach, O.; Heusler, F. Liebigs Ann. Chem. 1888, 243, 219.
23. (c) Merkushev, E. B. Synthesis 1988, 923.
24. (d) Gross, M. L.; Blank, D. H.; Welch, W. M. J. Org. Chem. 1993, 58, 2104.
25. (e) Satamurthy, N.; Barrio, J. B.; Bida, G. T.; Phelps, M. E. Tetrahedron Lett. 1990, 31, 4409.
26. (f) Cohen, T.; Dietz, A. G., Jr.; Miser, J. R. J. Org. Chem. 1977, 42, 2053.
27. (a) Nicolaou, K. C.; Boddy, C. N. C.; Natarajan, S.; Yue, T. Y.; Li, H.; Bräse, S.; Ramanjulu, J. M. J. Am. Chem. Soc. 1997, 119, 3421.
28. (b) Nicolaou, K. C.; Li, H.; Boddy, C. N. C.; Ramanjulu, J. M.; Yue, T. Y.; Natarajan, S.; Chu, X. J.; Bräse, S.; Rübsam, F. Chem. Eur. J. 1999, 5, 2584.
29. Knochel, P.; Yeh, M. C. P.; Berk, S. C.; Talbert, J. J. Org. Chem. 1988, 53, 2390.
30. Barnier, J. P.; Blanco, L. Synth. Commun. 2003, 33, 2487.
31. Nagono, T.; Hayashi, T. Org. Lett. 2005, 7, 491.
32. (a) Green, L.; Chauder, B.; Snieckus, V. J. Heterocycl. Chem. 1999, 36, 1453.
33. (b) Negishi, E.; Valente, L. F.; Kobayashi, M. J. Am. Chem. Soc. 1980, 102, 3298.
34. (c) Kobayashi, M.; Negishi, E. J. Org. Chem. 1980, 45, 5223.
35. (d) Negishi, E. Acc. Chem. Res. 1982, 15, 340.
36. (e) Tamaru, Y.; Ochiai, H.; Nakamura, T.; Yoshida, Z. Tetrahedron Lett. 1986, 27, 955.
37. (f) Klement, I.; Rottländer, M.; Tucker, C. E.; Majid, T. N.; Knochel, P.; Venegas, P.; Cahiez, G. Tetrahedron 1996, 52, 7201.
38. (a) Ishihara, K.; Hasegawa, A.; Yamamoto, H. Synlett 2002, 1296.
39. (b) Ishihara, K.; Hasegawa, A.; Yamamoto, H. Synlett 2002, 1299.
40. (a) Goodwin, S.; Smith, A. F.; Horning, E. C. J. Am. Chem. Soc. 1959, 81, 1903.
41. (b) Woodward, R. B.; Iacobucci, G. A.; Hochstein, F. A. J. Am. Chem. Soc. 1959, 81, 4434.
42. Van-Bac, N.; Moisand, C.; Gouyette, A.; Muzard, G.; Dat-Xuong, N.; Le Pecq, J. B.; Paoletti, C. Cancer Treat. Rep. 1980, 64, 879 and references cited therein.
43. Mathé, G.; Hayat, M.; De Vassal, F.; Schwarzenberg, L.; Schneider, M.; Schlumberger, J. R.; Jasmin, C.; Rosenfeld, C. Rev. Eur. Etud. Clin. Biol. 1970, 15, 541.
44. Sainsbury, M. Ellipticines. In Chemistry of Antitumour Agents; Wilman, D. E. V., Ed.; Blackie: Glasgow and London, UK, 1990.
45. Gribble, G. W. Synthesis and Antitumour Activity of Ellipticine Alkaloids and Related Compounds. In The Alkaloids; Brossi, A., Ed.; Academic Press: San Diego, CA, 1990; Vol. 39, p 239.
46. Gribble, G. W.; Saulnier, M. G. Heterocycles 1985, 23, 1277.
47. Gribble, G. W. Synthetic Approaches to the Ellipticine Alkaloids via Metalation and Cycloaddition Chemistry. In: Advances in Heterocyclic Natural Product Synthesis; W. H. Pearson, W. H., Ed.; Jai Press: Greenwich, CT, 1990; Vol. 1.
48. Gribble, G. W. Synlett 1991, 289.
49. Gribble, G. W.; Saulnier, M. G.; Sibi, M. P.; Obaza-Nutaitis, J. A. J. Org. Chem. 1984, 49, 4518.
50. May, C.; Moody, C. J. J. Chem. Soc., Chem. Commun. 1984, 926.
51. May, C.; Moody, C. J. J. Chem. Soc., Perkin Trans. 1988, 1, 247.
52. (a) Smith, P. A. S.; Brown, B. B. J. Am. Chem. Soc. 1951, 73, 2435.
53. (b) Jian, H.; Tour, J. M. J. Org. Chem. 2003, 68, 5091.
54. Jørgensen, M.; Krebs, F. C. J. Org. Chem. 2004, 69, 6688.
55. Musso, D. L.; Cochran, F. R.; Kelley, J. L.; McLean, E. W.; Selph, J. L.; Rigdon, G. C.; Orr, G. F.; Davis, R. G.; Cooper, B. R.; Styles, V. L.; Thompson, J. B.; Hall, W. R. J. Med. Chem. 2003, 46, 399.
56. Lewis, M. L.; de Meijere, A. Synlett 1997, 261.
57. Miller, R. B.; Stowell, J. G.; Dugar, S.; Moock, T. E.; Jenks, C. W.; Farmer, S. C.; Phan, B.; Wujcik, C. E.; Olmstead, M. M. Tetrahedron 2002, 58, 6061.
58. Knölker, H. S.; Reddy, K. R. Chem. Rev. 2002, 102, 4303.
59. Miller, R. B.; Moock, T. Tetrahedron Lett. 1980, 21, 3319.
60. Tobe, Y.; Utsumi, N.; Kawabata, K.; Nagono, A.; Adachi, K.; Araki, S.; Sonoda, M.; Hirose, K.; Naemura, K. J. Am. Chem. Soc. 2002, 124, 5350.
61. Harris, N. V.; Smith, C.; Bowden, K. Synlett 1990, 577.
62. Kondo, Y.; Kojima, S.; Sakamoto, T. J. Org. Chem. 1997, 62, 6507.
63. Lizos, D.; Tripoli, R.; Murphy, J. A. Chem. Commum. 2001, 2732.
64. Sha, C. K.; Yang, J. F. Tetrahedron 1992, 48, 10645.
65. Gribble, G. W.; Saulnier, M. G.; Obaza-Nutaitis, J. A.; Ketcha, D. M. J. Org. Chem. 1992, 57, 5891.