Synthesis of 2,2′-bipyrroles and 2,2′-thienylpyrroles from donor-acceptor cyclopropanes and 2-cyanoheteroles

Organic Letters

Volumn 6, Issue 6, 2004, Pages 1057-1059

  Yu, Ming ^a   Pantos, G Dan ^a   Sessler, Jonathan L ^a   Pagenkopf, Brian L ^a  

^a UNIVERSITY OF TEXAS AT AUSTIN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

2 CYANOPYRROLE DERIVATIVE; 2 CYANOTHIOPHENE; 2,2' BIPYRROLE DERIVATIVE; 2,2' THIENYLPYRROLE DERIVATIVE; CYCLOPROPANE DERIVATIVE; NITRILE; PYRROLE DERIVATIVE; THIOPHENE DERIVATIVE; TRIFLUOROMETHANESULFONIC ACID; TRIMETHYLSILYLTRIFLUOROMETHANESULFONATE; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; METHODOLOGY;

CYCLOPROPANES; MOLECULAR STRUCTURE; PYRROLES;

EID: 1642446192     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol049857h     Document Type: Article

References (53)

1. (a) Battersby, A. R. Nat. Prod. Rep. 2000, 17, 507-526.
2. (b) Milgrom, L. R. The Colours of Life; Oxford University Press: Oxford, 1997.
3. (c) Chlorophylls; Scheer, H., Ed.; CRC Press: Boca Raton, 1991.
4. (d) Falk, H. The Chemistry of Linear Oligopyrroles and Bile Pigments; Springer-Verlag: Wien, 1989.
5. Tittlemier, S. A.; Simon, M.; Jarman, W. M.; Elliott, J. E.; Norstrom, R. J. Environ. Sci. Technol. 1999, 33, 26-33.
6. Bauer, H. Chem. Ber. 1967, 100, 1704-1709.
7. van Haare, J. A. E. H.; van Boxtel, M.; Janssen, R. A. J. Chem. Mater. 1998, 10, 1166-1175.
8. (a) Gloe, K.; Stephan, H.; Grotjahn, M. Chem. Eng. Technol 2003, 26, 1107-1117.
9. (b) Sessler, J. L.; Camiolo, S.; Gale, P. A. Coord. Chem. Rew. 2003, 240, 17-55.
10. (c) Sessler, J. L.; An, D.; Cho, W.-S.; Lynch, V. M. J. Am. Chem. Soc. 2003, 125, 13646-13647.
11. (d) Sessler, J. L.; An, D.; Cho, W.-S.; Lynch, V. M. Angew. Chem., Int. Ed. 2003, 42, 2278-2281.
12. Sessler, J. L.; Gorden, A. E. V.; Seidel, D.; Hannah, S.; Lynch, V.; Gordon, P. L.; Donohoe, R. J.; Drew Tait, C.; Webster Keogh, D. Inorg. Chim. Acta 2002, 341, 54-70.
13. Fürstner, A. Angew. Chem., Int. Ed. 2003, 42, 3582-3603.
14. Kral, V.; Davis, J.; Andrievsky, A.; Kralova, J.; Synytsya, A.; Pouckova, P.; Sessler, J. L. J. Med. Chem. 2002, 45, 1075-1078.
15. (a) Bender, C. O.; Bonnett, R. J. Chem. Soc. C 1968, 2526-2528.
16. (b) Ceacareanu, D. M.; Gerstenberger, M. R. C.; Haas, A. J. Heterocycl. Chem. 1985, 22, 281-285.
17. (c) Boger, D. L.; Patel, M. Tetrahedron Lett. 1987, 28, 2499-2502.
18. (d) Boger, D. L.; Patel, M. J. Org. Chem. 1988, 53, 1405-1415.
19. (e) Falk, H.; Flödl, H. Monatsh. Chem. 1988, 119, 247-252.
20. (f) Glaser, M.; Gruner, M.; Viola, H. J. Prakt. Chem. 1994, 336, 363-365.
21. (g) Wasserman, H. H.; Petersen, A. K.; Xia, M.; Wang, J. Tetrahedron Lett. 1999, 40, 7587-7589.
22. (h) Oda, K.; Sakai, M.; Ohno, K.; Machida, M. Heterocycles 1999, 50, 277-282.
23. (a) Vogel, E.; Balci, M.; Kakumanu, P.; Kogh, P.; Lex, J.; Ermer, O. Angew. Chem., Int. Ed. Engl. 1987, 26, 928-931.
24. (b) Sessler, J. L.; Cyr, M. J.; Lynch, V.; McGhee, E.; Ibers, J. A. J. Am. Chem. Soc. 1990, 112, 2810-2813.
25. (c) Sessler, J. L.; Cyr, M.; Burrell, A. K. Tetrahedron 1992, 48, 9661-9672.
26. (d) Guilard, R.; Aukauloo, M. A.; Tardieux, C.; Vogel, E. Synthesis 1995, 1480-1482.
27. (e) Nonell, S.; Bou, N.; Borrell, J. I.; Teixido, J.; Villanueva, A.; Juarranz, J.; Cañete, M. Tetrahedron Lett. 1995, 36, 3405-3408.
28. (f) Johnson, M. R.; Slebodnick, C.; Ibers, J. A. J. Porphyrins Phthalocyanines 1997, 1, 87.
29. (g) Merz, A.; Kronberger, J.; Dunsch, L.; Neudeck, A.; Petr, A.; Parkenyi, L Angew. Chem., Int. Ed. 1999, 38, 1442-1446.
30. (h) Shevchuk, S. V.; Davis, J. M.; Sessler, J. L. Tetrahedron Lett. 2001, 42, 2447-2450.
31. Skowronek, P.; Lightner, D. A. Monatsh. Chem. 2003, 134, 889-899.
32. (j) Merz, A.; Anikin, S.; Lieser, B.; Heinze, J.; John, H. Chem.-Eur. J. 2003, 9, 449-455.
33. (a) Bordner, J.; Rapoport, H. J. Org. Chem. 1965, 30, 3824-3828.
34. (b) Brown, D.; Griffiths, D.; Rider, M. E.; Smith, R. C. J. Chem. Soc., Perkin Trans. I 1986, 455-463.
35. (c) D'Alessio, R.; Rossi, A. Synlett 1996, 513-514.
36. (d) Wu, J.; Vetter, W.; Gribble, G. W.; Schneekloth, J. S., Jr.; Blank, D. H.; Görls Angew. Chem., Int. Ed. 2002, 41, 1740-1743.
37. (a) D'Alession, R.; Rossi, A. Synlett 1996, 513-514.
38. (b) Fürstner, A.; Grabowski, J.; Lehmann, C. W. J. Org. Chem. 1999, 64, 8275-8280.
39. (c) Fürstner, A.; Grabowski, J.; Lehmann, C. W.; Kataoke, T.; Nagai, K. Chem. Biol. Chem. 2001, 2, 60-68.
40. (d) Melvin, M. S.; Calcutt, M. W.; Noftle, R. E.; Manderville, R. A. Chem. Res. Toxicol. 2002, 15, 742-748.
41. (a) Farnier, M.; Soth, S.; Fournari, P. Can. J. Chem. 1976, 54, 1074-1082.
42. (b) Hinz, W.; Jones, R. A.; Patel, S. U.; Karatza, M.-H. Tetrahedron 1986, 42, 3753-3758.
43. (c) Wasseman, H. H.; Lombardo. L. J. Tetrahedron Lett. 1989, 30, 1725-1728.
44. (d) Buchwald, S. L.; Wannamaker, M. W.; Watson, B. T. J. Am. Chem. Soc. 1989, 111, 776-777.
45. (e) Musicki, B. J. Org. Chem. 1990, 55, 910-918.
46. (f) Gupton, J. T.; Petrich, S. A.; Hicks, F. A.; Wilkinson, D. R.; Vargas, M.; Hosein, K.; Sikorski, J. A. Heterocycles 1998, 47, 689-702.
47. (g) Korostova, S. E.; Mikhaleva, A. I.; Trofimov, B. A. Russ. Chem. Rev. 1999, 68, 459-482.
48. (h) Barluenga, J.; Tomas, M.; Rubio, E.; Lopez-Pelegrin, J. A.; Garcia-Granda, S.; Perez Priede, M. J. Am. Chem. Soc. 1999, 121, 3065-3071.
49. Araki, S.; Tanaka, T.; Toumatsu, S.; Hirashita, T. Org. Biomol. Chem. 2003, 1, 4025-4029.
50. Yu, M.; Pagenkopf, B. L. Org. Lett. 2003, 5, 5099-5101.
51. Yu, M.; Pagenkopf, B. L. J. Am. Chem. Soc. 2003, 125, 8122-8123.
52. (a) Barnett, G. H.; Anderson, H. J.; Loader, C. E. Can. J. Chem. 1980, 58, 409-411.
53. (b) Loader, C. H.; Anderson, H. J. Can. J. Chem. 1981, 59, 2673-2676.