A Dipolar Cycloaddition Approach to Pyrrolo[l,2-a]indoles Using N-[(Trimethylsilyl)methyl]-Substituted Indoles

Journal of Organic Chemistry

Volumn 54, Issue 3, 1989, Pages 644-653

  Padwa, Albert ^a   Fryxell, Glen E ^a   Gasdaska, John R ^a   Venkatramanan, M K ^a   Wong, George S K ^a  

^a EMORY UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001543645     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00264a027     Document Type: Article

References (54)

1. Pinder, A. R. In The Alkaloids; Grundon, M. F., Ed.; Chemical Society: London, 1982; Vol. 12.
2. Padwa, A.; Hamilton, L. Tetrahedron Lett. 1965, 4363. Padwa, A.; Eisenhardt, W. J. Org. Chem. 1970, 35, 2472. Padwa, A.; Glazer, E. J. Am. Chem. Soc. 1972, 94, 7788; J. Org. Chem. 1973, 38, 284. Padwa, A.; Dean, D.; Mazzu, A.; Vega, E. J. Am. Chem. Soc. 1973, 95, 7168. Padwa, A.; Vega, E. J. Org. Chem. 1975, 40, 175. Padwa, A.; Ku, H. J. Org. Chem. 1979, 44, 255.
3. Huisgen, R.; Scheer, W.; Huber, H. J. Am. Chem. Soc. 1967, 89, 1753.
4. Lown, J. W. In 1,3-Dipolar Cycloaddition Chemistry; Padwa, A., Ed.; Wiley-Interscience: New York, 1984; Vol. 2.
5. Padwa, A.; Chen, Y. Y.; Koehler, K. F.; Tomas, M. Bull. Soc. Chim. Belg. 1983, 92, 811. Padwa, A.; Haffmanns, G.; Tomas, M. Tetrahedron Lett. 1983, 24, 4303. Padwa, A.; Haffmanns, G.; Tomas, M. J. Org. Chem. 1984, 49, 3314. Padwa, A.; Chiacchio, U.; Venkatramanan, M. K. J. Chem. Soc., Chem. Commun. 1985, 1108. Padwa, A.; Dent, W. J. Org. Chem. 1987, 52, 235.
6. Vedejs, E.; Martinez, G. R. J. Am. Chem. Soc. 1979, 101, 6452. Vedejs, E.; West, F. G. J. Org. Chem. 1983, 48,4773. Vedejs, E.; Martinez, G. R. J. Am. Chem. Soc. 1980, 102, 7993. Vedejs, E.; Larsen, S.; West, F. G. J. Org. Chem. 1985, 50, 2170.
7. Smith, R.; Livinghouse, T. J. Org. Chem. 1983, 48, 1554; J. Chem. Soc., Chem. Commun. 1983, 210.
8. Chen, S. F.; Ullrich, J. W.; Mariano, P. S. J. Am. Chem. Soc. 1983, 105, 6160.
9. Tsuge, O.; Kanemasa, S.; Kuraoka, S.; Tanenaka, S. Chem. Lett. 1984, 279. Tsuge, O.; Kanemasa, S.; Kuraoka, S. Bull. Chem. Soc. Jpn. 1985, 58, 1570. Tsuge, O.; Kanemasa, S.; Kuraoka, S.; Tanenaka, S. Chem. Lett. 1984, 281.Tsuge, O.; Kanemasa, S.; Matsuda, K. Chem. Lett. 1985, 1411. Tsuge, O.; Kanemasa, S.; Hatada, A.; Matsuda, K. Chem. Lett. 1984, 801. Tsuge, 0.; Kanemasa, S.; Yamada, T.; Matsuda, K. Heterocycles 1985, 23, 2489.
10. Terao, Y.; Imai, N.; Achiwa, K.; Sekiya, M. Chem. Pharm. Bull. 1982, 30, 3167. Achiwa, K.; Sekiya, M. Chem. Lett. 1981, 1213. Achiwa, K.; Motoyama, T.; Sekiya, M. Chem. Pharm. Bull. 1983, 31, 3939. Achiwa, K.; Sekiya, M. Heterocycles 1983, 20, 167. Achiwa, K.; Imai, N.; Inaoka, T.; Sekiya, M. Chem. Pharm. Bull. 1984, 32, 2878. Imai, N.; Terao, Y.; Achiwa, K. Heterocycles 1985, 23, 1107. Achiwa, K.; Sekiya, M. Tetrahedron Lett. 1982, 23, 2589. Achiwa, K.; Imai, N.; Motoyama, T.; Sekiya, M. Chem. Lett. 1984, 2041. Imai, N.; Terao, Y.; Achiwa, K.; Sekiya, M. Tetrahedron Lett. 1984, 25, 1579.
11. Miki, Y.; Hachiken, H.; Takemura, S.; Ikeda, M. Heterocycles 1984, 22, 701.
12. Padwa, A.; Chen, Y. Y. Tetrahedron Lett. 1983, 24, 3447. Padwa, A.; Chen, Y. Y.; Dent, W.; Nimmesgern, H. J. Org. Chem. 1985, 50, 4006. Padwa, A.; Dent, W.; Parker, K. A.; Cohen, I. D. Tetrahedron Lett. 1984, 25, 4917. Padwa, A.; Chen, Y. Y.; Chiacchio, U.; Dent, W. Tetrahedron 1985, 41, 3529. Padwa, A.; Dent, W.; Tomas, M.; Chen, Y. Y.; Chiacchio, U. J. Heterocycl. Chem. 1985, 22, 21. Padwa, A.; Gasdaska, J. R. J. Am. Chem. Soc. 1986, 108, 1104.
13. Grierson, D. S.; Harris, M.; Husson, H. P. J. Am. Chem. Soc. 1980, 102, 1064.
14. Overman, L. E.; Jacobsen, E. J. Tetrahedron Lett. 1982, 23, 2741.
15. Colvin, E. W. Chem. Soc. Rev. 1978, 7, 15. Chan, T. H.; Fleming, I. Synthesis 1979, 761.
16. Huisgen, R. Angew. Chem., Int. Ed. Engl. 1980, 19, 947.
17. Taylor, E. C.; Turchi, I. J. Chem. Rev. 1979, 79, 181.
18. Reimlinger, H. Chem. Ber. 1970, 103, 1900.
19. Atkinson, R. S.; Rees. C. W. Chem. Commun. 1967, 1232.
20. Vedejs, E.; Grissom, J. W.; Preston, J. K. J. Org. Chem. 1987, 52, 3488.
21. Speckamp, W. N.; Veenstra, S. J.; Dijkink; Fortgens, R. J. Am. Chem. Soc. 1981, 103, 4643.
22. Coates, R. M.; Hutchins, C. W. J. Org. Chem. 1979, 44, 4742.
23. Hegedus, L. S.; Allen, G. F.; Waterman, E. L. J. Am. Chem. Soc. 1976. 98. 2674.
24. Ito, Y.; Kobayashi, K.; Saegusa, T. J. Am. Chem. Soc. 1977, 99, 3532.
25. Person, H.; Pardo, M. D. A.; Foucaud, A. Tetrahedron Lett. 1980, 281.
26. Franck, R. W. Prog. Chem. Org. Nat. Prod. 1979, 38, 1.
27. Takahashi, K.; Kametani, T. Heterocycles 1978, 9, 293; 1979, 13, 411.
28. Remers, W. A. The Chemistry of Antitumor Antibiotics; Wiley-Interscience: New York, 1979; Vol. I.,pp 221–276.
29. Danishefsky, S.; Berman, E. M.; Ciufolini, M.; Etheredge, S. J.; Segmuller, B. E. J. Am. Chem. Soc. 1985, 107, 3891.
30. Rebek, J.; Shaber, S. H. Heterocycles 1981, 16, 1173.
31. Luly, J. R.; Rapoport, H. J. Org. Chem. 1984, 49, 1671.
32. Naruta, Y.; Nagai, H.; Maruyama, K. Chem. Lett. 1983, 1383.
33. Kishi, Y. J. Nat. Prod. 1979, 42, 549.
34. Allen. G. R.; Weiss. M. J. Med. Chem. 1967. 10. 1.
35. Kametani, T.; Kigawa, Y.; Nemoto, H.; Ihara, M.; Fukumoto, K. J. Chem. Soc. Perkin Trans. 1 1980, 1607.
36. Okamoto. M.; Shunsaku. O. Chem. Pharm. Bull. 1980.,28, 1071.
37. For a preliminary report, see: Padwa, A.; Gasdaska, J. R. J. Am. Chem. Soc. 1986, 108, 1104.
38. Huisgen, R. In 1,3-Dipolar Cycloaddition Chemistry; Padwa, A. Ed.; Wiley-Interscience; New York, 1984; Chapter 1.
39. Fleming, I. Frontier Orbitals and Organic Chemical Reactions; Wiley-Interscience: New York, 1976.
40. Houk, K. N.; Sims, J.; Luskus, L.; Watts, C. R. J. Am. Chem. Soc. 1973, 95, 7301.
41. Beugelmans, R.; Negron, G.; Roussi, G. J. Chem. Soc., Chem. Commun. 1983, 31. Beugelmans, R.; Benadjila-Iguertsira, L.; Roussi, G. J. Chem. Soc., Chem. Commun. 1982, 544. Chastanet, J.; Roussi, G. Heterocycles 1985, 23, 653.
42. The reduction of Ag(I) to the metallic state is somewhat reminiscent of results reported by Koser, G. F.; Fairclosth, J. J. J. Org. Chem. 1976, 41, 583.
43. Candy, C. F.; Jones, R. A.; Wright, P. H. J. Chem. Soc. C 1970, 2563.
44. Chadwick, D. J.; Meakins, G. D.; Rhode, C. A. J. Chem. Res. 1980, 42.
45. For a related diradical-dipole species, see: Stone, K. J.; Greenberg, M. M.; Goodman, J. L.; Peters, K. S.; Berson, J. A. J. Am. Chem. Soc. 1986, 108, 8088; 1987, 109, 1567.
46. Magnus, P.; Gallagher, T.; Brown, P.; Pappalardo, P. Acc. Chem. Res. 1984, 17, 35.
47. Marienelli, E. R. Tetrahedron Lett. 1982, 2745.
48. Shepherd, M. K. J. Chem. Soc. Perkin Trans. 1 1986, 1495.
49. Greenberg, M. M.; Blackstock, S. C.; Berson, J. A. Tetrahedron Lett. 1987, 4263.
50. Chauhan, P. M. S.; Jenkins, G.; Walker, S. M.; Storr, R. C. Tetrahedron Lett. 1988, 117.
51. Padwa, A.; Dent, W.; Nimmesgern, H.; Venkatramanan, M. K.; Wong, G. S. K. Chem. Ber. 1986, 119, 813.
52. Givens, R. S. Organic Photochemistry; Padwa, A., Ed.; 1981; Vol. 5, p 227.
53. Ratner, S.; Clarke, H. T. J. Am. Chem. Soc. 1937, 59, 200.
54. Kane, J. M. J. Org. Chem. 1980, 45, 5396.