A short procedure for the preparation of highly functionalized di- and tetrahydropyridines

Tetrahedron Letters

Volumn 40, Issue 20, 1999, Pages 3961-3964

  Bennasar, M Lluïsa ^a   Zulaica, Ester ^a   Juan, Cecília ^a   Llauger, Laura ^a   Bosch, Joan ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

Acylation; Enolates; Pyridines; Pyridinium salts

Indexed keywords

PYRIDINE DERIVATIVE;

ACYLATION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; HYDROGENATION; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033553359     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00621-8     Document Type: Article

References (23)

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2. 2. (a) Bennasar, M.-L.; Vidal, B.; Bosch, J. Chem. Commun. 1996, 2755-2756.
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5. 4. See also: Sammes, M. P.; Lee, C. M.; Katritzky, A. J. Chem. Soc., Perkin Trans. 1 1981, 2476.
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14. 9. For the introduction of a functionalized alkyl group at the α-position of the pyridine ring, see: (a) Dhar, T. G. M.: Gluchowski, C. Tetrahedron Lett. 1994, 35, 989-992.
15. (b) Comins, D. L.; Joseph, S. P. In Advances in Nitrogen Heterocycles, Moody, C. J., Ed.; JAI Press Inc.: London, 1996; Vol. 2, pp. 251-294, and references cited therein.
16. 10. For the addition of this kind of nucleophile to N-alkylpyridinium salts followed by acid-induced cyclization on the indole nucleus, see: (a) Wenkert, E. Pure Appl. Chem. 1981, 53, 1271.
17. (b) Wenkert, E.; Angell. E. C.; Drexler, J.; Moeller, P. D. R.; Pyrek, J. S.; Shi, Y. J.; Sultana, M.; Vankar, Y. D. J. Org. Chem. 1986, 51, 2995-3000.
18. (c) Spitzner, D.; Zaubitzer, T.; Shi, Y. J.; Wenkert, E. J. Org. Chem. 1988, 53, 2274-2278.
19. 11. For related examples on the hydrogenation of 1,4-dihydropyridines, see: Bennasar, M.-L.; Vidal, B.; Lázaro, A.; Kumar, R.; Bosch, J. Tetrahedron Lett. 1996, 37, 3541-3544. See also reference 2b.
20. 2Me), 208.9 (COMe).
21. 2Ph), 95.3, 95.6 (C-5), 108.9 (indole C-7), 113.9, 114.1 (indole C-3), 118.4 (indole C-4), 118.9 (indole C-5), 121.4 (indole C-6), 126.2 (indole C-2), 127.3, 127.5, 127.7, 127.9, 128.7, 135.9, 136.9 (Ph, indole C-3a, indole C-7a), 145.7, 146.4 (C-6), 168.0, 168.2, 173.7, 175.2, 207.2, 207.8 (CO).
22. 14. (a) Joule, J. A. In Indoles, The Monoterpenoid Indole Alkaloids, Saxton, J. E., Ed. In The Chemistry of Heterocyclic Compounds; Weissberger, A., Taylor, E. C., Eds.; Wiley: New York, 1983; Vol. 25, Part 4, pp 201-217.
23. (b) Alvarez, M.; Joule, J. In Monoterpenoid Indole Alkaloids, Saxton, J. E., Ed. In The Chemistry of Heterocyclic Compounds; Taylor, E. C., Ed.; Wiley: Chichester, 1994; Vol. 25, Supplement to Part 4, pp 217-229.