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Synthesis of Substituted Pyrroles via Ultrasound Assisted Three-component Coupling Reaction of Amines, α, β-Unsaturated Aldehydes and Nitroalkanes
Xiao Yi-Song,
Wang Yan-Guang,
Xiao Yi-Song
Department of Chemistry, Zhejiang University, Hangzhou, Zhejiang 310027, China
Search for more papers by this authorWang Yan-Guang
Department of Chemistry, Zhejiang University, Hangzhou, Zhejiang 310027, China
Search for more papers by this authorXiao Yi-Song,
Wang Yan-Guang,
Xiao Yi-Song
Department of Chemistry, Zhejiang University, Hangzhou, Zhejiang 310027, China
Search for more papers by this authorWang Yan-Guang
Department of Chemistry, Zhejiang University, Hangzhou, Zhejiang 310027, China
Search for more papers by this authorAbstract
An efficient synthesis of substituted pyrroles via ultrasound-assisted three-component coupling reaction of amines with a, β-unsaturated aldehydes and nitroalkanes is reported.
References
- 1(a) Franck, B; Nonn, A., Angew. Chem., Int. Ed. Engl. 1995, 34, 1795. (b) Coookson, G. H.; Riminton, C., Biochem. J. 1953, 57, 476. (c) Baltazzi, E., J. Chem. Rev. 1963, 63, 511.
- 2(a) Itoh, S; Fukui, Y; Haranou, S; Ogino, M; Komatsu, M. Ohshiro, Y., J. Org. Chem. 1992, 57, 4452. (b) Woo, J; Sigurdsson, S. T.; Hopkins, P. B., J. Am. Chem. Soc. 1993, 115, 3407. (c) Weidner, M. F.; Sigurdsson, S. T.; Compto, D. R., Biochemistry 1990, 29, 9225. (d) Lainton, J. A. H.; Huffinan, J. W.; Martin, B. R. Compto, D. R., Tetrahedron Lett. 1995, 36, 1401.
- 3(a) Khanna, I. K.; Weter, R. M.; Yu, Y. Collins, P. W.; Miyashio, J. M.; Kobddt, C. M.; Veenhuizen, A. W.; Currie, J. L.; Seibert, K; Isakson, P., C.J. Med. Chem. 1997, 40, 1619. (b) Kimura, T; Noguchi, Y; Nakao, A., Eur. Pat. Appl. EP 799823, 1997 [Chem. Abstr. 1997, 727, 331392c]. (c) Tatsuta, K., Jpn. Kokai Tokkyo Koho JP 07206 815 1995 [Chem. Abstr. 1996, 124, 8609].
- 4(a) Kleinspehn, G. G., J. Am. Chem. Soc. 1955, 77, 1546. (b) Trost, B. M.; Keinan, E., J. Org. Chem. 1980, 45, 2741. (c) Escribano, F. C.; Alcantara, M. P. D. Gomez, A., Tetrahedron Lett. 1988, 29, 6001. (d) Berree, F; Marchand, E; Morel, G., Tetrahedron Lett. 1992, 33, 6155. (e) Sethy, L; Ivan, J; Gilbert, R., Tetrahedron Let. 1999, 40, 4177. (f) Periasamy, M; Srinivas, G; Bharathi, P., J. Org. Chem. 1999, 64, 4204. (g) Katritzky, A. R.; Zhang, L; Yao, J., J. Org. Chem. 2000, 65, 8074. (h) Grigg, R; Savic, V., Chem. Commun. (Cambridge) 2000, 873. (i) Dieter, R. K.; Yu, H., Org. Lett. 2000, 2, 2283. (j) Cheung, K. M.; Shoolingin-Jordan, P. M., Synthesis 2001, 1627.
- 5(a)
Donrs, N. T.,
Tetrahedron Lett.
1999,
40,
3957.
(b)
Surya, H. R. P.;
Jothilingam, S.,
Tetrahedron Lett.
2001,
42,
6595.
10.1016/S0040-4039(01)01334-X Google Scholar(c) Knorr, L., Chem. Ber. 1984, 17, 1635.10.1002/cber.18840170220 Google Scholar(d) Patterson, J. M., Synthesis 1976, 281.
- 6 Shiraish, H; Nishitani, T; Sakagushi, S., J. Org. Chem. 1998, 63, 6234.
- 7 Shiraish, H; Nishitani, T; Niahihara, T; Sakagushi, S; Ishii, Y., Tetrahedron 1999, 55, 13957.
- 8(a) Ranu, B. C.; Hajra, A; Jana, U., Synlett 2000, 1, 75. (b) Ranu, B. C.; Hajra, A. Tetrahedron 2001, 57, 4767.
- 9(a) Rajender, S. V.; Kannan, P. N., Tetrahedron Lett. 1998, 39, 7463. (b) Tuncay, A; Anaclerio, B. M.; Zolodz, M., Tetrahedron Lett. 1999, 40, 599. (c) Ribeiro, C. M. R.; Brenelli, E. C. S.; Passaroto, E. N., Tetrahedron Lea. 2001, 42, 6477.
