Modular one-pot synthesis of tetrasubstituted pyrroles from α-(alkylideneamino)nitriles

Journal of Organic Chemistry

Volumn 72, Issue 19, 2007, Pages 7083-7090

  Bergner, Ines ^a   Opatz, Till ^a,b  

^a JOHANNES GUTENBERG UNIVERSITY   (Germany)

^b UNIVERSITY OF HAMBURG   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; OLEFINS; PARAFFINS; REACTION KINETICS; SYNTHESIS (CHEMICAL);

CONVERGENT CONSTRUCTION; NITROALKANES; TETRASUBSTITUTED PYRROLES;

PIGMENTS;

ALDEHYDE DERIVATIVE; ALKENE; HYDROGEN CYANIDE; NITRILE; NITROALKANE; NITROUS ACID; PYRROLE; PYRROLE DERIVATIVE;

ARTICLE; CYCLOADDITION; ONE POT SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

ALDEHYDES; ALKENES; CYCLIZATION; NITRILES; NITRO COMPOUNDS; PYRROLES;

EID: 34548774478     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo070426x     Document Type: Article

References (54)

1. Bailly, C. Curr. Med. Chem. - Anti-Cancer Agents 2004, 4, 363-378.
2. Christophersen, C. In Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1985, Vol. 24, pp 25-111.
3. Le Quesne, P. W.; Dong, Y.; Blythe, T. A. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Pergamon: Oxford, U.K., 1999; Vol. 13, pp 237-287.
4. Fuerstner, A. Angew. Chem., Int. Ed. 2003, 42, 3582-3603.
5. Faulkner, D. J. Nat. Prod. Rep. 1998, 15, 113-158.
6. Milgrom, L. R. The Colors of Life: an Introduction to the Chemistry of Porphyrins and Related Compounds; Oxford University Press: Oxford, U.K., 1997.
7. The Porphyrin Handbook; Kadish, K. M., Smith, K. M., Guilard, R., Eds.; Academic Press: San Diego, CA, 2000.
8. Kashman, Y.; Koren-Goldshlager, G.; Gravalos, M. D. G.; Schleyer, M. Tetrahedron Lett. 1999, 40, 997-1000.
9. Pindur, U.; Kim, Y. S.; Mehrabani, F. Curr. Med. Chem. 1999, 6, 29-69.
10. Biava, M.; Fioravanti, R.; Porretta, G. C.; Deidda, D.; Maullu, C.; Pompei, R. Bioorg. Med. Chem. Lett. 1999, 9, 2983-2988.
11. Loya, S.; Rudi, A.; Kashman, Y.; Hizi, A. Biochem. J. 1999, 344, 85-92.
12. MacDiarmid, A. G. Synth. Met. 1997, 84, 27-34.
13. Guernion, N. J. L.; Hayes, W. Curr. Org. Chem. 2004, 8, 637-651.
14. Roth, B. D. (Warner-Lambert Co.) EP Patent 409281, 1991.
15. Knorr, L. Ber. Dtsch. Chem. Ges. 1884, 17, 1635-1642.
16. Paal, C. Ber. Dtsch. Chem. Ges. 1885, 18, 367-371.
17. Braun, R. U.; Mueller, T. J. J. Synthesis 2004, 2391-2406.
18. Hantzsch, A. Ber. Dtsch. Chem. Ges. 1890, 23, 1474-1476.
19. Van Leusen, A. M.; Siderius, H.; Hoogenboom, B. E.; Van Leusen, D. Tetrahedron Lett. 1972, 5337-5340.
20. Gribble, G. W.; Saulnier, M. G.; Pelkey, E. T.; Kishbaugh, T. L. S.; Liu, Y.; Jiang, J.; Trujillo, H. A.; Keavy, D. J.; Davis, D. A.; Conway, S. C.; Switzer, F. L.; Roy, S.; Silva, R. A.; Obaza-Nutaitis, J. A.; Sibi, M. P.; Moskalev, N. V.; Barden, T. C.; Chang, L.; Habeski, W. M.; Peleman, B.; Sponholtz, W. R., III; Chau, R. W.; Allison, B. D.; Garaas, S. D.; Sinha, M. S.; McGowan, M. A.; Reese, M. R.; Harpp, K. S. Curr. Org. Chem. 2005, 9, 1493-1519.
21. Huisgen, R.; Gotthardt, H.; Bayer, H. O.; Schaefer, F. C. Chem. Ber. 1970, 103, 2611-2624.
22. St. Cyr, D. J.; Martin, N.; Arndtsen, B. A. Org. Lett. 2007, 9, 449-452.
23. Balme, G. Angew. Chem., Int. Ed. 2004, 43, 6238-6241.
24. Shimizu, M.; Takahashi, A.; Kawai, S. Org. Lett. 2006, 8, 3585-3587.
25. Joshi, U.; Pipelier, M.; Naud, S.; Dubreuil, D. Curr. Org. Chem. 2005, 9, 261-288.
26. Tejedor, D.; Gonzalez-Cruz, D.; Garcia-Tellado, F.; Marrero-Tellado, J. J.; Rodriguez, M. L. J. Am. Chem. Soc. 2004, 126, 8390-8391.
27. Bellina, F.; Rossi, R. Tetrahedron 2006, 62, 7213-7256.
28. Padwa, A.; Gruber, R.; Pashayan, D. J. Org. Chem. 1968, 33, 454-455.
29. Binder, J. T.; Kirsch, S. F. Org. Lett. 2006, 8, 2151-2153.
30. Tsuge, O.; Ueno, K.; Kanemasa, S.; Yorozu, K. Bull. Chem. Soc. Jpn. 1986, 59, 1809-1824.
31. Tsuge, O.; Ueno, K.; Kanemasa, S.; Yorozu, K. Bull. Chem. Soc. Jpn. 1987, 60, 3347-3358.
32. Meyer, N.; Opatz, T. Synlett 2004, 787-790.
33. Meyer, N.; Werner, F.; Opatz, T. Synthesis 2005, 945-956.
34. Bergner, I.; Opatz, T. Synthesis 2007, 918-928.
35. Baldwin, J. E.; Cutting, J.; Dupont, W.; Kruse, L.; Silberman, L.; Thomas, R. C. J. Chem. Soc., Chem. Commun. 1976, 736-738.
36. Grigg, R.; Kemp, J.; Malone, J.; Tangthongkum, A. J. Chem. Soc., Chem. Commun. 1980, 648-650.
37. Alva Astudillo, M. E.; Chokotho, N. C. J.; Jarvis, T. C.; Johnson, C. D.; Lewis, C. C.; McDonnell, P. D. Tetrahedron 1985, 41, 5919-5928.
38. Tatsukawa, A.; Kawatake, K.; Kanemasa, S.; Rudzinski, J. M. J. Chem. Soc., Perkin Trans. 2 1994, 2525-2530.
39. Pearson, W. H.; Stay, P. Synlett 2003, 903-921.
40. Arrieta, A.; Otaegui, D.; Zubia, A.; Cossio, F. P.; Diaz-Ortiz, A.; delaHoz, A.; Herrero, M. A.; Prieto, P.; Foces-Foces, C.; Pizarro, J. L.; Arriortua, M. I. J. Org. Chem. 2007, 72, 4313-4322.
41. While both conventional and microwave heating furnished crude pyrroles with surprisingly clean NMR spectra, TLC also indicated the formation of undefined polar (polymeric?) side products in all cases. This largely accounts for the deviation of the combined yields of compounds 8 and 9 from unity.
42. Barton, D. H. R.; Kervagoret, J.; Zard, S. Z. Tetrahedron 1990, 46, 7587-7598.
43. Attempts to prepare 2,3,4,5-tetraalkyl-substituted pyrroles have so far met with little success. The intermediate formation of enamines from the pronucleophiles may account for this behavior.
44. Haake, G.; Struve, D.; Montforts, F.-P. Tetrahedron Lett. 1994, 35, 9703-9704.
45. Grob, C. A.; Camenisch, K. Helv. Chim. Acta 1953, 36, 49-58.
46. Ballini, R.; Petrini, M. Tetrahedron 2004, 60, 1017-1047.
47. Nef, J. U. Liebigs Ann. Chem. 1894, 280, 263-291.
48. Kawai, Y.; Inaba, Y.; Tokitoh, N. Tetrahedron: Asymmetry 2001, 12, 309-318.
49. Alles, G. A. J. Am. Chem. Soc 1932, 54, 271-274.
50. Leroux, M. L.; Le Gall, T.; Mioskowski, C. Tetrahedron: Asymmetry. 2001, 12, 1817-1823.
51. Tamura, R.; Hayashi, K.; Kai, Y.; Oda, D. Tetrahedron Lett. 1984, 25, 4437-4440.
52. Robertson, D. N. J. Org. Chem. 1960, 25, 47-49.
53. Ballini, R.; Barboni, L.; Giarlo, G. J. Org. Chem. 2004, 69, 6907-6908.
54. Kraus, K. W.; Dolter, R. J.; Petrowski, G. E.; Bogan, R. T.; Buenker, R. J.; Plamondon, J. E.; Miller, J. J.; Whalen, D. L.; Koopman, D. J. Proc. Iowa Acad. Sci. 1970, 76, 127-134.