Synthetic methods for γ-lactam and pyrrole derivatives exploiting a three-component coupling strategy

Tetrahedron Letters

Volumn 45, Issue 6, 2004, Pages 1195-1197

  Clique, Blandine ^a   Anselme, Colas ^a   Otto, Daniela ^a   Monteiro, Nuno ^a   Balme, Geneviève ^a  

^a CPE LYON   (France)

Author keywords

Aromatization; Hydrogenation; Lactams; Pyrroles; Rearrangement

Indexed keywords

AMINE; CARBOXYLIC ACID DERIVATIVE; GAMMA LACTAM DERIVATIVE; PHENOL DERIVATIVE; PYRROLINE DERIVATIVE; SULFONE DERIVATIVE; VINYL DERIVATIVE;

AROMATIZATION; ARTICLE; CHEMICAL ANALYSIS; COMPLEX FORMATION; HYDROGENOLYSIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0742322006     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2003.11.142     Document Type: Article

References (14)

1. Katritsky A.R., Rees C.W., Scriven E.F.V. Comprehensive Heterocyclic Chemistry II. 1996;Pergamon, Oxford.
2. Mitchinson A., Nadin A. J. Chem. Soc., Perkin Trans. 1. 17:2000;2862-2892. and previous annual reports.
3. For recent reviews, see: Balme G., Bossharth E., Monteiro N. Eur. J. Org. Chem. 2003;4101-4111.
4. Hulme C., Gore V. Curr. Med. Chem. 10:2003;51-80.
5. Orru R.V.A., de Greef M. Synthesis. 2003;1471-1499.
6. Zhu J. Eur. J. Org. Chem. 2003;1133-1144.
7. Bienaymé H., Hulme C., Oddon G., Schmitt P. Chem. Eur. J. 6:2000;3321-3329.
8. Dömling A., Ugi I. Angew. Chem., Int. Ed. 39:2000;3168-3210.
9. Clique B., Vassiliou S., Monteiro N., Balme G. Eur. J. Org. Chem. 2002;1493-1499.
10. 2 (10 mol %) as catalyst. However, three successive operations with new loadings of catalyst were needed in order to achieve a total conversion (73% yield).
11. +) 370.1655, found 370.1660.
12. We had already observed the same phenomenon during the hydrogenation of analogous furan derivatives: Garçon S., Cavicchioli M., Vassiliou S., Hartmann B., Monteiro N., Balme G. J. Org. Chem. 66:2001;4069-4073.
13. +) 366.1341, found 366.1347.
14. It should be noted that pyrroles 6 could not be obtained from pyrrolidines 2 using the same oxidation conditions.