Tautomer-dependent Bergman cyclization of novel uracil-enediyne chimeras

Chemistry - A European Journal

Volumn 6, Issue 9, 2000, Pages 1555-1558

  Kim, Chang Sik ^a   Diez, Christian ^a   Russell, Keith C ^a  

^a University of Miami   (United States)

Author keywords

Cyclizations; Diradicals electrocyclic reactions; Enynes; Tautomerism

Indexed keywords

ALKYNE DERIVATIVE; URACIL;

AROMATIZATION; ARTICLE; CHEMICAL REACTION KINETICS; CHEMOREACTIVITY; CYCLIZATION; ISOMER; REACTION ANALYSIS; STRUCTURE ACTIVITY RELATION;

EID: 0034595402     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3765(20000502)6:9<1555::AID-CHEM1555>3.0.CO;2-M     Document Type: Article

References (44)

1. a) R. R. Jones, R. G. Bergman, J. Am. Chem. Soc. 1972, 94, 660-661;
2. b) R. G. Bergman, Acc. Chem. Res. 1973, 6, 25-31;
3. c) N. Darby, C. U. Kim, J. A. Salaum, K. W. Shelton, S. Takada, S. Masamune, J. Chem. Soc. Chem. Commun. 1971, 1516-1517;
4. d) J. Mayer, F. Sondheimer, J. Am. Chem. Soc. 1966, 88, 602-604.
5. For an excellent overview of the biology and chemistry of enediynes see: Enediyne Antibiotics as Anticancer Agents (Eds.: D. B. Borders, T. W. Doyle), Marcel Dekker, New York, 1995.
6. a) K. C. Nicolaou, A. L. Smith, S. V. Wendeborn, C.-K. Hwang, J. Am. Chem. Soc. 1991, 113, 3106-3114;
7. b) P. A. Wender, C. K. Zercher, J. Am. Chem. Soc. 1991, 113, 2311-2313.
8. a) J. Porco, J. A., F. J. Schoenen, T. J. Stout, J. Clardy, S. L. Schreiber, J. Am. Chem. Soc. 1990, 112, 7410-7411;
9. b) K. C. Nicolaou, W.-M. Dai, Y. P. Hong, S.-C. Tsay, K. K. Baldridge, J. S. Siegel, J. Am. Chem. Soc. 1993, 115, 7944-7953.
10. K. C. Nicolaou, W.-M. Dai, S. V. Wendeborn, A. L. Smith, Y. Torisawa, P. Maligres, C. K. Hwang, Angew. Chem. 1991, 103, 1034-1038; Angew. Chem. Int. Ed. Engl. 1991, 30, 1032-1036.
11. K. C. Nicolaou, W.-M. Dai, S. V. Wendeborn, A. L. Smith, Y. Torisawa, P. Maligres, C. K. Hwang, Angew. Chem. 1991, 103, 1034-1038; Angew. Chem. Int. Ed. Engl. 1991, 30, 1032-1036.
12. A. Basak, J. C. Shain, Tetrahedron Lett. 1998, 39, 3029-3030;
13. b) B. P. Warner, S. P. Millar, R. D. Broene, S. L. Buchwald, Science 1995, 269, 814-816;
14. c) B. König, H. Hollnagel, B. Ahrens, P. G. Jones, Angew. Chem. 1995, 107, 2763-2765; Angew. Chem. Int. Ed. Engl. 1995, 34, 2538-2540;
15. c) B. König, H. Hollnagel, B. Ahrens, P. G. Jones, Angew. Chem. 1995, 107, 2763-2765; Angew. Chem. Int. Ed. Engl. 1995, 34, 2538-2540;
16. d) M. M. McPhee, S. M. Kerwin, J. Org. Chem. 1996, 61, 9385-9393.
17. Y. Naoe, J. Kikuishi, K. Ishigaki, H. Iitsuka, H. Nemoto, M. Shibuya, Tetrahedron Lett. 1995, 36, 9165-9168.
18. a) M. Shibuya, M. Wakayama, Y. Naoe, T. Kawakami, K. Ishigaki, H. Nemoto, H. Shimizu, Y. Nagao, Tetrahedron Lett. 1996, 37, 865-868;
19. b) A. G. Myers, B. Zheng, J. Am. Chem. Soc. 1996, 118, 4492-4493.
20. J. W. Grissom, D. Klingberg, D. Huang, B. J. Slattery, J. Org. Chem. 1997, 62, 603-626.
21. a) K. Ohe, M. Kojima, K. Yonehara, S. Uemura, Angew. Chem. 1996, 108, 1959-1962; Angew. Chem. Int. Ed. Engl. 1996, 35, 1823-1825;
22. a) K. Ohe, M. Kojima, K. Yonehara, S. Uemura, Angew. Chem. 1996, 108, 1959-1962; Angew. Chem. Int. Ed. Engl. 1996, 35, 1823-1825;
23. b) Y. Wang, M. G. Finn, J. Am. Chem. Soc. 1995, 117, 8045-8046;
24. c) B. P. Warner, S. P. Millar, R. D. Broene, S. L. Buchwald, Science 1995, 269, 814-816.
25. M. Schmittel, S. Kiau, Chem. Lett. 1995, 953-954.
26. M. H. Maier, B. Greiner, Liebigs, Ann. Chem. 1992, 855-861.
27. M. F. Semmelhack, T. Neu, F. Foubelo, J. Org. Chem. 1994, 59, 5038-5047;
28. b) M. F. Semmelhack, T. Neu, F. Foubelo, Tetrahedron Lett. 1992, 33, 3277-3280.
29. K. C. Nicolaou, A. Liu, Z. Zeng, S. McComb, J. Am. Chem. Soc. 1992, 114, 9279-9282.
30. C.-S. Kim, K. C. Russell, J. Org. Chem. 1998, 63, 8229-8234.
31. a) R. L. Funk, E. R. R. Young, R. M. Williams, M. F. Flanagan, T. L. Tricia L. Cecil, J. Am. Chem. Soc. 1996, 118, 3291-3292;
32. b) N. J. Turro, A. Evenzabav, K. C. Nicolaou, Tetrahedron Lett. 1994, 35, 8089-8092;
33. c) D. Ramkumar, M. Kalpana, B. Varghese, S. Sankararaman, J. Org. Chem. 1996, 61, 2247-2250;
34. d) T. Kaneko, M. Takahashi, M. Hirama, Angew. Chem. 1999, 111, 1347-1349; Angew. Chem. Int. Ed. 1999, 38, 1267-1268.
35. d) T. Kaneko, M. Takahashi, M. Hirama, Angew. Chem. 1999, 111, 1347-1349; Angew. Chem. Int. Ed. 1999, 38, 1267-1268.
36. a) A. C. Schroeder, A. Bloch, J. L. Perman, M. Bobek, J. Med. Chem. 1982, 25, 1255-1258;
37. b) J. Goodchild, R. A. Porter, R. H. Raper, I. S. Sim, R. M. Upton, J. Viney, H. J. Wadsworth, J. Med. Chem. 1983, 26, 1252-1257;
38. c) E. De Clercq, J. Deschamps, J. Balzarini, J. Giziewicz, P. J. Barr, M. J. Robins, J. Med. Chem. 1983, 26, 661-666.
39. N. Choy, K. C. Russell, Heterocycles 1999, 51, 13-16.
40. The products from the bulk cyclization gave the expected spectral data. In the case of 10 and 11, the products were compared with authentic benzoyleneurca and 1,3-dimethyl benzolyeneurea, respectively.
41. a) W. Roth, H. Hopf, T. Wasser, H. Zimmerman, C. Werner, Liebigs Ann. 1996, 1691-1695;
42. b) T. Kaneko, M. Takahashi, M. Hirama, Tetrahedron Lett. 1999, 41, 2015-2018.
43. a) C.-S. Kim, K. C. Russell, Tetrahedron Lett. 1999, 40, 3835-3838;
44. b) M. Hirama, Pure Appl. Chem. 1997, 69, 525-530.