Competition and co-operation between ortho directing groups and activating agents: Regioselective metallations of 1-(methoxyphenyl)pyrroles

Tetrahedron

Volumn 53, Issue 13, 1997, Pages 4883-4888

  Faigl, Ferenc ^a   Fogassy, Katalin ^a   Thurner, Angelika ^a   Toke, László ^a  

^a BUDAPEST UNIVERSITY OF TECHNOLOGY AND ECONOMICS   (Hungary)

Author keywords

[No Author keywords available]

Indexed keywords

PYRROLE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; INFRARED SPECTROPHOTOMETRY; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030968328     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00183-X     Document Type: Article

References (21)

1. Schlosser, M. Organoalkali Reagents. In Organometallics in Synthesis: A Manual; Schlosser, M., Editor; John Willey: Chichester, 1994; pp. 1-166.; Gray, M.; Tinl, M.; Snieckus, V. Lithium. In Comprehensive Organometallic Chemistry II.; McKillop, A., Vol. Ed.; Elsevier: Oxford, 1995; pp. 1-92.
2. Schlosser, M. Organoalkali Reagents. In Organometallics in Synthesis: A Manual; Schlosser, M., Editor; John Willey: Chichester, 1994; pp. 1-166.; Gray, M.; Tinl, M.; Snieckus, V. Lithium. In Comprehensive Organometallic Chemistry II.; McKillop, A., Vol. Ed.; Elsevier: Oxford, 1995; pp. 1-92.
3. Snieckus, V. Chem. Rev. 1990, 90, 879-933.; especially pp. 883-884 and the references cited therein.
4. Solcum, W.D.; Moon, R.; Thompson, J.; Coffey, D.S.; Didi, J.; Solcum, M.G. Tetrahedron Lett. 1994, 35, 385-388.
5. Morton, A.A. J. Am. Chem. Soc. 1947, 69, 969-971.
6. Katsoulos, G.; Takagishi, S.; Schlosser, M. Synlett 1991, 731-732.
7. Mills, R.J.; Snieckus, V. Tetrahedron Lett. 1984, 25, 479-480.; Takagishi, S.; Katsoulos, G.; Schlosser, M. Synlett 1992, 360-361.; Schlosser, M.; Simig, Gy. Tetrahedron Lett. 1991, 32, 1965-1966.
8. Mills, R.J.; Snieckus, V. Tetrahedron Lett. 1984, 25, 479-480.; Takagishi, S.; Katsoulos, G.; Schlosser, M. Synlett 1992, 360-361.; Schlosser, M.; Simig, Gy. Tetrahedron Lett. 1991, 32, 1965-1966.
9. Mills, R.J.; Snieckus, V. Tetrahedron Lett. 1984, 25, 479-480.; Takagishi, S.; Katsoulos, G.; Schlosser, M. Synlett 1992, 360-361.; Schlosser, M.; Simig, Gy. Tetrahedron Lett. 1991, 32, 1965-1966.
10. Schlosser, M.; Katsoulos, G.; Takagishi, S. Synlett 1990, 747-748.
11. One to one mixture of 13 and (1-(4-carboxy-3-methoxyphenyl)pyrrole was isolated with 20 % over all yield when 2 was treated with butyllithium in diethyl ether - hexane mixture at 0°C for 3 hours and then carboxylated with dry ice.
12. Faigl, F.; Schlosser, M. Tetrahedron 1993, 49, 10271-10278.
13. Faigl, F.; Schlosser, M. unpublished results (1992).
14. Bauer, W.; Schleyer, P.R. J. Am. Chem. Soc. 1989, 111, 7191-7198.
15. Bauer, W.; Winchester, W.R.; Schleyer, P.R. Organometallics 1987, 6, 2371-2379.
16. Wakefield, B.J. Organolithium Methods. In Best Synthetic Methods; Katritzky, A.R.; Meth-Chon, O.; Rees, C.W., Ser, Eds.; Academic Press: London, 1988; pp. 18-19.
17. Elming, N.; Clauson-Kaas, N. Acta Chemica Scandinavica 1952, 6, 867-874.
18. Gross, H. Chem.Ber. 1962, 95, 2270-2275.
19. Salmón, M.; Carbajal, E.; Aguilar, M.; Saloma, M.; Juarez, C. J. Chem. Soc. Chem. Commun. 1983, 1532-1533.
20. Giuliano, R.; Poretta, G.C.; Scalzo, M.; Chimenti, F.; Artico, M.; Dolfini, E.; Morasca, L. Farmaco Ed. Sci. 1972, 27, 1091-1103.
21. South African Patent 7,201,129 (1973) (C.A.: 81 963478e).