Regioselective synthesis of alkylpyrroles from imines and nitroalkenes by lanthanide compounds

Tetrahedron

Volumn 55, Issue 49, 1999, Pages 13957-13964

  Shiraishi, Hiroyuki ^a   Nishitani, Takayuki ^a   Nishihara, Tatsuo ^a   Sakaguchi, Satoshi ^a   Ishii, Yasutaka ^a  

^a KANSAI UNIVERSITY   (Japan)

Author keywords

Imines; Nitroalkenes; Pyrroles; Samarium compounds

Indexed keywords

ALKENE DERIVATIVE; IMINE; INDOLE DERIVATIVE; LANTHANIDE; PYRROLE DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; PRIORITY JOURNAL; SYNTHESIS;

EID: 0033521103     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00855-8     Document Type: Article

References (24)

1. 1. a) Baltazzi, E.; Krimen, L.I. Chem. Rev. 1963, 63, 511.
2. b) Jones, R.A.; Bean, G.P. "The Chemistry of Pyrroles", Academic Press, New York, 1977.
3. c) Chadwick, D. J. "Comprehensive Hetrocyclic Chemistry" vol 4, Peramon Press. p. 155 (1984).
4. 2. Friedman, M. J. Org. Chem. 1965, 30, 859.
5. 3. a) Kleinspehn, G. G. J. Am. Chem. Soc. 1955, 77, 1546.
6. b) Hendricson, J. B.; Rees, R.; Templeton, J. F. J. Am. Chem. Soc. 1964, 86, 107.
7. c) Young, D. M.; Allen, C. F. H. Org. Synth. 1943, II, 219.
8. d) Roomi, M. W.; MacDonald, S. F. Can. J. Chem. 1970, 48, 1689.
9. e) McKinnon, D. M. Can. J. Chem. 1965, 43, 2628.
10. f) Trost, B. M.; Keinan, E. J. Org. Chem. 1980, 45, 2741.
11. g) Murahashi, S.; Shimamura, T.; Moritani, J. J. Chem. Soc., Chem. Commun. 1974, 931.
12. h) Schulte, K. E.; Reisch, J.; Walker, H. Chem. Ber. 1965, 98, 98.
13. i) Hauptmann, S.; Weissenfels, M.; Scholz, M.; Werner, E.-M.; Koehler, H.-J.; Weisflog, J. Tetrahedron Lett. 1968, 11, 1317.
14. (j) Escribano, F. C.; Alcantara, M. P. D.; Gomez-Sanchea, A. Tetrahedron Lett. 1988, 29, 6001.
15. k) Fischer, H. Org. Synth. II 1943, 202.
16. 4. Roskamp, E. J.; Dragovich, P. S.; Hartung, Jr. J. B.; Pedersen, S.F. J. Org. Chem. 1989, 54, 4736.
17. 5. Shiraishi, H.; Nishitani, T.; Sakagushi, S; Ishii, Y. J. Org. Chem. 1998, 63, 6234.
18. 6. a) Noland, W. E.; Baude, F.J. Org. Synth. V 1973, 567.
19. b) Batcho, A. D.; Leimgruber, W. Org. Synth. 1984, 63, 214.
20. 7. "Lanthanides: Chemistry and Use in Organic Synthesis", Kobayashi, S. Ed.; Springer: New York (1999).
21. 8. a) Morris, M. L.; Sturgess, M. A. Tetrahedron Lett. 1993, 34, 43.
22. b) Dumez, E.; Rodriguez, J.; Dulcere, J.-P. Chem. Commun. 1997, 1831.
23. 9. a) Miyashita, M.; Kumazawa, T.; Yoshikoshi, A. J. Org. Chem. 1980, 45, 2945.
24. b) Melot, J. M.; Texier-Boullet, F.; Foucaud, A. Tetrahedron 1988, 44, 2215.