Intermolecular [4π + 2π]-Cycloadditions of aromatic methyleneamines

Tetrahedron Letters

Volumn 38, Issue 38, 1997, Pages 6741-6744

  Campos, Pedro J ^a   Lamaza, Igor ^a   Rodríguez, Miguel A ^a   Canal, Gonzalo ^b  

^a UNIVERSITY OF LA RIOJA   (Spain)

^b Depto de Investigación FAES   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIC AMINE;

ARTICLE; CHEMICAL MODIFICATION; DRUG SYNTHESIS; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030841635     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)01541-4     Document Type: Article

References (17)

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2. (b) Barluenga, J.; Campos, P.J.; Canal, G. Synthesis, 1989, 33.
3. (c) Barluenga, J.; Bayón, A.M.; Campos, P.J.; Canal, G.; Asensio, G.; González-Nun~ez, E.; Molina, Y. Chem. Ber., 1988, 121, 1813.
4. Barluenga J., Bayón A.M., Campos P.J., Asensio G., González-Nun~ez E., Molina Y. J. Chem. Soc., Perkin Trans. 1:1988;1631.
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8. See reference , p. 258.
9. (a) Seebach, D.; Beck, A.K.; Studer, A. In Modern Synthetic Methods 1995; Ernst, B.; Leumann, C. Eds., VCH: Basel, 1995, p. 1.
10. (b) Smith, D.A.; Houk, K.N. Tetrahedron Lett., 1991, 32, 1549.
11. Silverstein, R.M.; Bassler, G.B.; Morrill, T.C. Spectroscopic Identification of Organic Compounds; Wiley: New York, 1981.
12. 15a, 3.6%.
13. (a) Michael, J.P. Nat. Prod. Rep., 1995, 12, 465.
14. (b) Magnus, P.; Parry, D.; Iliadis, T.; Eisenbeis, S.A.; Fairhurst, R.A. J. Chem. Soc., Chem. Commun., 1994, 1543.
15. (a) Carling, R.W.; Leeson, P.D.; Moseley, A.M.; Smith, J.D.; Saywell, K.; Trickleblank, M.D.; Kemp, J.A.; Marshall, G.R.; Foster, A.C.; Grinwood, S. Bioorg. Med. Chem. Lett., 1993, 3, 65.
16. (b) Moromoto, Y.; Matsuda, F.; Shirahama, H. Synlett, 1991, 202.
17. 4 (0.2 mmol, 0.019 g, except for 4a) in the same solvent under an argon atmosphere. The mixture was heated at reflux (40°C for 4a) and the aromatic N-(methoxymethyl)arylamine was added and the mixture stirred for 6 hours at the same temperature. The solution was hydrolized and standard work-up and column chromatography (silica gel; hexane-ether) gave pure 1,2,3,4-tetrahydroquinoline.