Biradicals from thermolysis of N-[2-(1-alkynyl)phenyl]-N'- phenylcarbodiimides and their subsequent transformations to 6H-indolo[2,3- b]quinolines

Journal of Organic Chemistry

Volumn 64, Issue 3, 1999, Pages 925-932

  Shi, Chongsheng ^a   Zhang, Quan ^a   Wang, Kung K ^a  

^a WEST VIRGINIA UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CYANAMIDE; QUINOLINE DERIVATIVE;

AROMATIZATION; ARTICLE; CHEMICAL REACTION; MOLECULAR INTERACTION; SYNTHESIS;

EID: 0033525049     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981845k     Document Type: Article

References (54)

1. Shi, C.; Wang, K. K. J. Org. Chem. 1998, 63, 3517-3520.
2. Schmittel, M.; Steffen, J.-P.; Angel, M. A. W.; Engels, B.; Lennartz, C.; Hanrath, M. Angew. Chem., Int. Ed. Engl. 1998, 37, 1562-1564.
3. (a) Jones, R. R.; Bergman, R. G. J. Am. Chem. Soc. 1972, 94, 660-661.
4. (b) Lockhart, T. P.; Comita, P. B.; Bergman, R. G. J. Am. Chem. Soc. 1981, 103, 4082-4090.
5. (c) Bharucha, K. N.; Marsh, R. M.; Minto, R. E.; Bergman, R. G. J. Am. Chem. Soc. 1992, 114, 3120-3121.
6. For recent reviews, see: (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.
7. For recent reviews, see: (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.
8. (a) Myers, A. G.; Kuo, E. Y.; Finney, N. S. J. Am. Chem. Soc. 1989, 111, 8057-8059.
9. (b) Myers, A. G.; Dragovich, P. S. J. Am. Chem. Soc. 1989, 111, 9130-9132.
10. (c) Nagata, R.; Yamanaka, H.; Okazaki, E.; Saito, I. Tetrahedron Lett. 1989, 30, 4995-4998.
11. (d) Nagata, R.; Yamanaka, H.; Murahashi, E.; Saito, I. Tetrahedron Lett. 1990, 31, 2907-2910.
12. (e) Wang, K. K.; Wang, Z.; Tarli, A.; Gannett, P. J. Am. Chem. Soc. 1996, 118, 10783-10791 and references therein.
13. (f) Grissom, J. W.; Klingberg, D.; Huang, D.; Slattery, B. J. J. Org. Chem. 1997, 62, 603-626 and references therein.
14. (a) Moore, H. W.; Yerxa, B. R. Chemtracts 1992, 273-313.
15. (b) Tarli, A.; Wang, K. K. J. Org. Chem. 1997, 62, 8841-8847.
16. (a) David, W. M.; Kerwin, S. M. J. Am. Chem. Soc. 1997, 119, 1464-1465.
17. (b) Hoffner, J.; Schottelius, M. J.; Feichtinger, D.; Chen, P. J. Am. Chem. Soc. 1998, 120, 376-385.
18. (c) Braverman, S.; Duar, Y.; Freund, M. Isr. J. Chem. 1985, 26, 108-114.
19. (a) Maier, M. E. Synlett 1995, 13-26.
20. (b) Nicolaou, K. C.; Dai, W.-H. Angew. Chem., Int. Ed. Engl. 1991, 30, 1387-1416.
21. (a) Differding, E.; Ghosez, L. Tetrahedron Lett. 1985, 26, 1647-1650.
22. (b) Molina, P.; Alajarin, M.; Vidai, A.; Sánchez-Andrada, P. J. Org. Chem. 1992, 57, 929-939.
23. Gillmann, T.; Hulsen, T.; Massa, W.; Wocadlo, S. Synlett 1995, 1257-1259.
24. Wilt, J. W.; Aznavoorian, P. M. J. Org. Chem. 1978, 43, 1285-1286.
25. (a) Schmittel, M.; Steffen, J.-P.; Auer, D.; Maywald, M.Tetrahedron Lett. 1997, 38, 6177-6180.
26. (b) Schmittel, M.; Strittmatter, M.; Kiau, S. Angew. Chem., Int. Ed. Engl. 1996, 35, 1843-1845.
27. (c) Schmittel, M.; Kiau, S.; Siebert, T.; Strittmatter, M. Tetrahedron Lett. 1996, 37, 7691-7694.
28. (d) Schmittel, M.; Strittmatter, M.; Vollmann, K.; Kiau, S. Tetrahedron Lett. 1996, 37, 999-1002.
29. (e) Schmittel, M.; Maywald, M.; Strittmatter, M. Synlett 1997, 165-166.
30. (f) Schmittel, M.; Strittmatter, M.; Kiau, S. Tetrahedron Lett. 1995, 36, 4975-4978.
31. (g) Garcia, J. G.; Ramos, B.; Pratt, L. M.; Rodriguez, A. Tetrahedron Lett. 1995, 36, 7391-7394.
32. 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.
33. After the original manuscript had been submitted for publication, a similar study was reported: Schmittel, M.; Steffen, J.-P.; Engels, B.; Lennartz, C.; Hanrath, M. Angew. Chem., Int. Ed. Engl. 1998, 37, 2371-2373.
34. (a) Molina, P.; Alajarín, M.; Vidal, A. J. Chem. Soc., Chem. Commun. 1990, 1277-1279.
35. (b) Saito, T.; Ohmori, H.; Furuno, E.; Motoki, S. J. Chem. Soc., Chem. Commun. 1992, 22-24.
36. (c) Saito, T.; Ohmori, H.; Ohkubo, T.; Motoki, S. J. Chem. Soc., Chem. Commun. 1993, 1802-1803.
37. (a) Peczyńska-Czoch, W.; Pognan, F.; Kaczmarek, L.; Boratyń-ski, J. J. Med. Chem. 1994, 37, 3503-3510.
38. (b) Kaczmarek, L.; Balicki, R.; Nantka-Namirski, P.; Peczyhska-Czoch, W.; Mordarski, M. Arch. Pharm. (Weinheim) 1988, 321, 463-467.
39. Alajarin, M.; Molina, P.; Vidal, A. J. Nat. Prod. 1997, 60, 747-748.
40. (a) Sharaf, M. H. M.; Schiff, P. L., Jr.; Tackie, A. N.; Phoebe, C. H., Jr.; Martin, G. E. J. Heterocycl. Chem. 1996, 33, 239-243.
41. (b) Cimanga, K.; De Bruyne, T.; Pieters, L.; Claeys, M.; Vlietinck, A. Tetrahedron Lett. 1996, 37, 1703-1706.
42. Marsili, A. Tetrahedron 1968, 24, 4981-4991.
43. (a) Shioiri, T.; Ninomiya, K.; Yamada, S.-i. J. Am. Chem. Soc. 1972, 94, 6203-6205.
44. (b) Ninomiya, K.; Shioiri, T.; Yamada, S. Tetrahedron 1974, 30, 2151-2157.
45. (c) Rigby, J. H.; Balasubramanian, N. J. Org. Chem. 1989, 54, 224-228.
46. Horner, L.; Oediger, H. Justus Liebigs Ann. Chem. 1959, 627, 142-162.
47. Gribble, G. W.; Saulnier, M. G. J. Chem. Soc., Chem. Commun. 1984, 168-169.
48. (a) Armstrong, R. N.; Ammon, H. L.; Darnow, J. N. J. Am. Chem. Soc. 1987, 109, 2077-2082.
49. (b) Newman, M. S.; Hussey, A. S. J. Am. Chem. Soc. 1947, 69, 3023-3027.
50. (a) Pindur, U.; Erfanian-Abdoust, H. Liebigs Ann. Chem. 1988, 803-805.
51. (b) Pindur, U.; Erfanian-Abdoust, H. Chem. Rev. 1989, 89, 1681-1689.
52. (a) Villemin, D.; Goussu, D. Heterocycles 1989, 29, 1255-1261.
53. (b) Arcadi, A.; Cacchi, S.; Marinelli, F. Tetrahedron Lett. 1989, 30, 2581-2584.
54. (c) Iritani, K.; Matsubara, S.; Utimoto. K. Tetrahedron Lett. 1988, 29, 1799-1802.