Cyclocondensation of α-aminonitriles and enones: A short access to 3,4-dihydro-2H-pyrrole 2-carbonitriles and 2,3,5-trisubstituted pyrroles

Journal of Organic Chemistry

Volumn 74, Issue 21, 2009, Pages 8243-8253

  Bergner, Ines ^a   Wiebe, Christine ^a   Meyer, Nino ^b   Opatz, Till ^a  

^a UNIVERSITY OF HAMBURG   (Germany)

^b JOHANNES GUTENBERG UNIVERSITY   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

AMINONITRILES; CARBONITRILES; CHEMICAL EQUATIONS; CYCLOCONDENSATION; ELECTROCYCLIZATION; ONE-POT REACTION; PYRROLIZIDINES; STARTING MATERIALS; UNSATURATED CARBONYL COMPOUNDS;

ACETONITRILE; AMINES; CARBONYLATION; MICROWAVE IRRADIATION; NITROGEN COMPOUNDS; UNSATURATED COMPOUNDS;

POTASSIUM COMPOUNDS;

AMINOACETONITRILE; ANION; BASE; CARBONYL DERIVATIVE; CYANIDE; HYDROGEN CYANIDE; NITRILE; PYRROLE DERIVATIVE; PYRROLIZIDINE;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; MICROWAVE IRRADIATION; POLYMERIZATION; PROTON TRANSPORT;

EID: 70350710079     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo901759u     Document Type: Article

References (42)

1. Woodward, R. B.; Hoffmann, R. Angew. Chem., Int. Ed. Engl. 1969, 8, 781-853.
2. Hunter, D. H.; Steiner, R. P. Can. J. Chem. 1975, 53, 355-365.
3. Hunter, D. H.; Sim, S. K.; Steiner, R. P. Can. J. Chem. 1977, 55, 1229-1241.
4. Wolf, G.; Würthwein, E. U. Chem. Ber. 1991, 124, 655-663.
5. Kloetgen, S.; Froehlich, R.; Würthwein, E.-U. Tetrahedron 1996, 52, 14801-14812.
6. Wolf, G.; Würthwein, E. U. Tetrahedron Lett. 1988, 29, 3647-3650.
7. Wolf, G.; Würthwein, E. U. Chem. Ber. 1991, 124, 889-896.
8. Hauser, C. R.; Taylor, H. M.; Ledford, T. G. J. Am. Chem. Soc. 1960, 82, 1786-1789.
9. Enders, D.; Shilvock, J. P. Chem. Soc. Rev. 2000, 29, 359-373.
10. Opatz, T. Synthesis 2009, 1941-1959.
11. Kison, C.; Meyer, N.; Opatz, T. Angew. Chem., Int. Ed. 2005, 44, 5662-5664.
12. Tsuge, O.; Ueno, K.; Kanemasa, S.; Yorozu, K. Bull. Chem. Soc. Jpn. 1986, 59, 1809-1824.
13. Tsuge, O.; Kanemasa, S.; Yorozu, K.; Ueno, K. Bull. Chem. Soc. Jpn. 1987, 60, 3359-3366.
14. Meyer, N.; Opatz, T. Synlett 2004, 787-790.
15. Kanemasa, S.; Tsuge, O. Adv. Cycloaddit. 1993, 3, 99-159.
16. Xiang, Y. B.; Drenkard, S.; Baumann, K.; Hickey, D.; Eschenmoser, A. Helv. Chim. Acta 1994, 77, 2209-2250.
17. de la Hoz, A.; Diaz-Ortiz, A.; Moreno, A. Adv. Org. Synth. 2005, 1, 119-171.
18. Koch, J.; Robert, J. F.; Panouse, J. J. C. R. Seances Acad. Sci. C 1978, 286, 95-98.
19. Sammes, M. P.; Chung, M. W. L.; Katritzky, A. R. J. Chem. Soc., Perkin Trans. 1 1985, 1773-1779.
20. Tasheva, D.; Petrova, A.; Simova, S. Synth. Commun. 2007, 37, 3971-3979.
21. Huisgen, R.; Gotthardt, H.; Bayer, H. O. Chem. Ber. 1970, 103, 2368-2387.
22. Lakhlifi, T.; Sedqui, A.; Fathi, T.; Laude, B.; Robert, J.-F. Can. J. Chem. 1994, 72, 1417-1423.
23. Pandey, G.; Lakshmaiah, G.; Ghatak, A. Tetrahedron Lett. 1993, 34, 7301-7304.
24. Mkairi, A.; Hamelin, J. Tetrahedron Lett. 1987, 28, 1397-1400.
25. Saito, T.; Kobayashi, S.; Ohgaki, M.; Wada, M.; Nagahiro, C. Tetrahedron Lett. 2002, 43, 2627-2631.
26. Lagriffoul, P.-H.; Tadros, Z.; Taillades, J.; Commeyras, A. J. Chem. Soc., Perkin Trans. 2 1992, 1279-1285.
27. Kurtz, P.; Disselnkoetter, H. Justus Liebigs Ann. Chem. 1972, 764, 69-93.
28. Paventi, M.; Edward, J. T. Can. J. Chem. 1987, 65, 282-289.
29. Pascal, R.; Taillades, J.; Commeyras, A. Tetrahedron 1980, 36, 2999-3008.
30. McKay, A. F.; Paris, G. Y.; Garmaise, D. L. J. Am. Chem. Soc. 1958, 80, 6276-6280.
31. Severin, T.; Adhikary, P.; Dehmel, E.; Eberhard, I. Chem. Ber. 1971, 104, 2856-2863.
32. MacClean, I. S.; Widdows, S. T. J. Chem. Soc. 1914, 105, 2169-2175.
33. Robinson, T. P.; Hubbard, R. B.; Ehlers, T. J.; Arbiser, J. L.; Goldsmith, D. J.; Bowen, J. P. Bioorg. Med. Chem. 2005, 13, 4007-4013.
34. Misra, S. S. J. Indian Chem. Soc. 1975, 52, 1095-1096.
35. Nadar, P. A.; Renuga, V. J. Indian Chem. Soc. 2006, 83, 1219-1222.
36. Straus, F.; Ecker, O. Ber. Dtsch. Chem. Ges. 1906, 39, 2977-3006.
37. Marcas, G. B.; Municio, A. M.; Vega, S. An. R. Soc. Esp. Fis. Quim., Ser. B 1964, 60, 639-652.
38. F̈urstner, A.; Weintritt, H.; Hupperts, A. J. Org. Chem. 1995, 60, 6637-6641.
39. de Laszlo, S. E.; Visco, D.; Agarwal, L.; Chang, L.; Chin, J.; Croft, G.; Forsyth, A.; Fletcher, D.; Frantz, B.; Hacker, C.; Hanlon, W.; Harper, C.; Kostura, M.; Li, B.; Luell, S.; MacCoss, M.; Mantlo, N.; O'Neill, E. A.; Orevillo, C.; Pang, M.; Parsons, J.; Rolando, A.; Sahly, Y.; Sidler, K.; Widmer, W. R.; O'Keefe, S. J. Bioorg. Med. Chem. Lett. 1998, 8, 2689-2694.
40. Chiu, P. K.; Sammes, M. P. Tetrahedron 1988, 44, 3531-3538.
41. Pitts, M. R.; Harrison, J. R.; Moody, C. J. J. Chem. Soc., Perkin Trans. 1 2001, 955-977.
42. Poggi, R.; Saltini, P. Gazz. Chim. Ital. 1932, 62, 678-686.