A facile synthesis of 3-alkoxy and 3-amino pyrroles

Tetrahedron Letters

Volumn 40, Issue 50, 1999, Pages 8789-8792

  Breuil Desvergnes, Valérie ^a   Compain, Philippe ^a,b   Vatèle, Jean Michel ^a   Goré, Jacques ^a  

^a UNIVERSITÉ LYON 1   (France)

^b Université d'Orléans   (France)

Author keywords

[No Author keywords available]

Indexed keywords

3 ALKOXYPYRROLE; 3 AMINOPYRROLE; BENZOIC ACID DERIVATIVE; HYDRAZONE DERIVATIVE; HYDROCHLORIC ACID; ORGANOLITHIUM COMPOUND; PYRROLE DERIVATIVE; PYRROLINE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; REACTION ANALYSIS; SYNTHESIS;

EID: 0033544763     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01869-9     Document Type: Article

References (11)

1. Breuil-Desvergnes, V.; Compain, P.; Vatèle, J. M.; Goré, J. Tetrahedron Lett. 1999, 40, 5009-5012.
2. (a) Terry, W. G.; Jackson, A. H.; Kenner, G. W.; Kornis, G. J. Chem. Soc. 1965, 4389-4393.
3. (b) Padwa, A.; Chen, Y. Y.; Dent, W.; Nimmesgern, H. J. Org. Chem. 1985, 50, 4006-4014.
4. (c) Padwa, A.; Norman, B. H. J. Org. Chem. 1990, 55, 4801-4807.
5. (d) Lash T. D.; Hoehner, M. C. J. Heterocyclic Chem. 1991, 28, 1671-1675.
6. (e) Corriu, R. J. P.; Bolin, G.; Iqbal, J.; Moreau, J. J. E.; Vernhet, C. Tetrahedron 1993, 49, 4603-4618.
7. (f) Xu, Z.; Lu, X. J. Org. Chem. 1998, 63, 5031-5041.
8. See for examples: Dieck, H. T.; Verfürth, U.; Diblitz, K.; Ehlers, J.; Fendesak, G. Chem. Ber. 1989, 129-131. Nedolya, N.A.; Brandsma, L.; Tarasova, O. A.; Verkruijsse, H. D.; Trofimov, B. A. Tetrahedron Lett. 1998, 39, 2409-2410.
9. See for examples: Dieck, H. T.; Verfürth, U.; Diblitz, K.; Ehlers, J.; Fendesak, G. Chem. Ber. 1989, 129-131. Nedolya, N. A.; Brandsma, L.; Tarasova, O. A.; Verkruijsse, H. D.; Trofimov, B. A. Tetrahedron Lett. 1998, 39, 2409-2410.
10. A comparable mechanism has been proposed for the formation of a nitrile from an N-oxide of hydrazone: Enders, D.; Schiffers, R. Synthesis 1996, 53-58.
11. The formation and transformation of an azetidinium species has been already proposed: Poitout, L.; Le Merrer, Y.; Depezay, J. C. Tetrahedron Lett. 1996, 37, 1613-1616 and references cited therein.