Biradicals/zwitterions from enallene-isonitriles. Formal [4 + 1] cycloadditions leading to 11H-indeno[1,2-b]quinoline and related compounds

Organic Letters

Volumn 5, Issue 18, 2003, Pages 3277-3280

  Lu, Xiaoling ^a   Petersen, Jeffrey L ^a   Wang, Kung K ^a  

^a WEST VIRGINIA UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

11H INDENO[1,2 B]QUINOLINE; AMPHOLYTE; ISONITRILE DERIVATIVE; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;

AROMATIZATION; ARTICLE; CYCLOADDITION; REACTION ANALYSIS; SUBSTITUTION REACTION;

EID: 0141744682     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol035143f     Document Type: Article

References (51)

1. (a) Jones, R. R.; Bergman, R. G. J. Am. Chem. Soc. 1972, 94, 660-661.
2. (b) Lockhart, T. P.; Comita, P. B.; Bergman, R. G. J. Am. Chem. Soc. 1981, 103, 4082-4090.
3. For reviews, see: (c) Nicolaou, K. C.; Dai, W.-H. Angew. Chem., Int. Ed. Engl. 1991, 30, 1387-1416. (d) Wang, K. K. Chem. Rev. 1996, 96, 207-222. (e) Grissom, J. W.; Gunawardena, G. U.; Klingberg, D.; Huang, D. Tetrahedron 1996, 52, 6453-6518.
4. For reviews, see: (c) Nicolaou, K. C.; Dai, W.-H. Angew. Chem., Int. Ed. Engl. 1991, 30, 1387-1416. (d) Wang, K. K. Chem. Rev. 1996, 96, 207-222. (e) Grissom, J. W.; Gunawardena, G. U.; Klingberg, D.; Huang, D. Tetrahedron 1996, 52, 6453-6518.
5. For reviews, see: (c) Nicolaou, K. C.; Dai, W.-H. Angew. Chem., Int. Ed. Engl. 1991, 30, 1387-1416. (d) Wang, K. K. Chem. Rev. 1996, 96, 207-222. (e) Grissom, J. W.; Gunawardena, G. U.; Klingberg, D.; Huang, D. Tetrahedron 1996, 52, 6453-6518.
6. (a) Myers, A. G.; Kuo, E. Y.; Finney, N. S. J. Am. Chem. Soc. 1989, 111, 8057-8059.
7. (b) Myers, A. G.; Dragovich, P. S. J. Am. Chem. Soc. 1989, 111, 9130-9132.
8. (c) Nagata, R.; Yamanaka, H.; Okazaki, E.; Saito, I. Tetrahedron Lett. 1989, 30, 4995-4998.
9. (d) Nagata, R.; Yamanaka, H.; Murahashi, E.; Saito, I. Tetrahedron Lett. 1990, 31, 2907-2910.
10. (a) Schmittel, M.; Strittmatter, M.; Kiau, S. Tetrahedron Lett. 1995, 36, 4975-4978.
11. (b) Schmittel, M.; Strittmatter, M.; Vollmann, K.; Kiau, S. Tetrahedron Lett. 1996, 37, 999-1002.
12. (c) Schmittel, M.; Strittmatter, M.; Kiau, S. Angew. Chem., Int. Ed. Engl. 1996, 35, 1843-1845.
13. (d) Schmittel, M.; Kiau, S.; Siebert, T.; Strittmatter, M. Tetrahedron Lett. 1996, 37, 7691-7694.
14. (e) Schmittel, M.; Keller, M.; Kiau, S.; Strittmatter, M. Chem. Eur. J. 1997, 3, 807-816.
15. (f) Schmittel, M.; Steffen, J.-P.; Maywald, M.; Engels, B.; Helten, H.; Musch, P. J. Chem. Soc., Perkin Trans. 2 2001, 1331-1339.
16. (a) Karlsson, J. O.; Nguyen, N. V.; Foland, L. D.; Moore, H. W. J. Am. Chem. Soc. 1985, 107, 3392-3393.
17. (b) Foland, L. D.; Karlsson, J. O.; Perri, S. T.; Schwabe, R.; Xu, S. L. ; Patil, S.; Moore, H. W. J. Am. Chem. Soc. 1989, 111, 975-989.
18. (c) Chow, K.; Nguyen, N. V.; Moore, H. W. J. Org. Chem. 1990, 55, 3876-3880.
19. (d) Tarli, A.; Wang, K. K. J. Org. Chem. 1997, 62, 8841-8847.
20. (e) For an excellent review, see: Moore, H. W.; Yerxa, B. R. Chemtracts 1992, 273-313.
21. (a) Shi, C.; Wang, K. K. J. Org. Chem. 1998, 63, 3517-3520.
22. (b) Schmittel, M.; Steffen, J.-P.; Angel, M. A. W.; Engels, B.; Lennartz, C.; Hanrath, M. Angew. Chem., Int. Ed. 1998, 37, 1562-1564.
23. (a) Shi, C.; Zhang, Q.; Wang, K. K. J. Org. Chem. 1999, 64, 925-932.
24. (b) Zhang, Q.; Shi, C.; Zhang, H.-R.; Wang, K. K. J. Org. Chem. 2000, 65, 7977-7983.
25. (c) Lu, X.; Petersen, J. L.; Wang, K. K. J. Org. Chem. 2002, 67, 5412-5415.
26. (d) Lu, X.; Petersen, J. L.; Wang, K. K. J. Org. Chem. 2002, 67, 7797-7801.
27. (e) Li, H.; Petersen, J. L.; Wang, K. K. J. Org. Chem. 2003, 68, 5512-5518.
28. (f) Schmittel, M.; Steffen, J.-P.; Engels, B.; Lennartz, C.; Hanrath, M. Angew. Chem., Int. Ed. 1998, 37, 2371-2373.
29. (g) Schmittel, M.; Rodríguez, D.; Steffen, J.-P. Angew. Chem., Int. Ed. 2000, 39, 2152-2155.
30. (h) Alajarín, M.; Molina, P.; Vidal, A. J. Nat. Prod. 1997, 60, 747-748.
31. (a) David, W. M.; Kerwin, S. M. J. Am. Chem. Soc. 1997, 119, 1464-1465.
32. (b) Feng, L.; Kumar, D.; Kerwin, S. M. J. Org. Chem. 2003, 68, 2234-2242.
33. (a) Wang, K. K.; Wang, Z.; Sattsangi, P. D. J. Org. Chem. 1996, 61, 1516-1518.
34. (b) Gillmann, T.; Heckhoff, S. Tetrahedron Lett. 1996, 37, 839-840.
35. Wu, M.-J.; Lin, C.-F.; Chen, S.-H.; Lee, F.-C. J. Chem. Soc., Perkin Trans. 1 1999, 2875-2876.
36. (a) Rainier, J. D.; Kennedy, A. R.; Chase, E. Tetrahedron Lett. 1999, 40, 6325-6327.
37. (b) Rainier, J. D.; Kennedy, A. R. J. Org. Chem. 2000, 65, 6213-6216.
38. (c) Suginome, M.; Fukuda, T.; Ito, Y. Org. Lett. 1999, 1, 1977-1979.
39. Debbert, S. L.; Cramer, C. J. Int. J. Mass Spectrom. 2000, 201, 1-15.
40. Obrecht, R.; Herrmann, R.; Ugi, I. Synthesis 1985, 400-402.
41. Ugi, I.; Meyr, R. Organic Syntheses; Willy: New York, 1973; Collect. Vol. V, pp 1060-1063.
42. (a) Landor, P. D. In The Chemistry of the Allenes; Landor, S. R., Ed.; Academic Press: London, 1982; Vol. 1, pp 44-47.
43. (b) Jacobs, T. L.; Dankner, D. J. Org. Chem. 1957, 22, 1424-1427.
44. Structure was established by X-ray structure analysis.
45. (a) Wall, M. E.; Wani, M. C. In The Alkaloids; Cordell, G. A., Ed.; Academic Press: San Diego, 1998; Vol. 50, pp 509-536.
46. (b) Curran, D. P.; Liu, H.; Josien, H.; Ko, S.-B. Tetrahedron 1996, 52, 11385-11404.
47. Katritzky, A. R.; Schwarz, O. A.; Rubio, O. Help. Chim. Acta 1984, 67, 939-946.
48. Rodima, T.; Kaljurand, I.; Pihl, A.; Mäemets, V.; Leito, I.; Koppel, I. A. J. Org. Chem. 2002, 67, 1873-1881.
49. (a) Sakamoto, T.; Kondo, Y.; Yamanaka, H. Heterocycles 1986, 24, 31-32.
50. (b) Kondo, Y.; Kojima, S.; Sakamoto, T. J. Org. Chem. 1997, 62, 6507-6511.
51. (c) Yasuhara, A.; Kanamori, Y.; Kaneko, M.; Numata, A.; Kondo, Y.; Sakamoto, T. J. Chem. Soc., Perkin Trans. 1 1999, 529-534.