Iodocyclization of 1,4-dihydropyridines

Tetrahedron Letters

Volumn 39, Issue 28, 1998, Pages 5089-5092

  Lavilla, Rodolfo ^a   Coll, Oscar ^a   Nicolàs, Marta ^a   Bosch, Joan ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

Cyclization; Halogenation; Oxazolidines; Pyridines

Indexed keywords

1,4 DIHYDROPYRIDINE DERIVATIVE;

ARTICLE; CYCLIZATION; IODINATION; NUCLEAR OVERHAUSER EFFECT; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 0032500159     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)00912-5     Document Type: Article

References (22)

1. [1] Eisner U, Kuthan J. Chem. Rev. 1972;72:1-42.
2. [2] Stout DM, Meyers AI. Chem. Rev. 1982;82:223-243.
3. [3] Sausins A, Duburs G. Khim. Geterotsikl. Soedin. 1993;579-612.
4. [4] Sausins A, Duburs G. Heterocycles 1988;27:291-314.
5. [5] Kutney JP. Heterocycles 1977;7:593-613.
6. [6] Comins DL, O'Connor S. Adv. Heterocycl. Chem. 1988;44:199-267.
7. [7] Bennasar M.-L, Bosch J. Synlett 1995; 587-596.
8. [8] Bennasar M.-L, Vidal B, Bosch J. Chem. Commun. 1996;2755-2756.
9. [9] Bennasar M.-L, Vidal B, Bosch J. J. Org. Chem. 1997;62:3597-3609.
10. [10] Goldmann S, Stoltefuss J. Angew. Chem. Int. Ed. Engl. 1991;30:1559-1578.
11. [11] Lavilla R, Gullón F, Barón X. Bosch J. Chem. Commun. 1997;213-214.
12. [12] Lavilla R, Kumar R, Coll O, Masdeu C, Bosch, J. Unpublished results.
13. [13] Lavilla R, Coll O, Kumar R, Bosch J. J. Org. Chem. 1998;63:2728-2730.
14. [14] Brewster ME, Simay A, Czako K, Winwood D, Farag U, Bodor N. J. Org. Chem. 1989;54:3721-3726.
15. [15] Wong Y-S, Marazano C, Gnecco D, Das BC. Tetrahedron Lett. 1994;35:707-710.
16. [16] Wong Y-S, Marazano C, Gnecco D, Génisson Y, Chiaroni A, Das BC. J. Org. Chem. 1997;62:729-733.
17. [17] Deslongchamps P. Stereoelectronic Effects in Organic Chemistry. Oxford: Pergamon Press, 1983;211-221.
18. [18] Amman R, Spitzner D. Angew, Chem. Int. Ed. Engl. 1991;30:1320-1321.
19. [19] Mangeney P, Gosmini R, Raussou S, Commerçon M, Alexakis A. J. Org. Chem. 1994;59:1877-1888.
20. [20] Gnecco D, Marazano C, Das BC. J. Chem. Soc. Chem. Commun. 1991:625-626.
21. [21] For a recent example of halocyclization upon a chiral oxazolidine, see: Agami C., Couty F, Hamon L, Venier O. J. Org. Chem. 1997;62:2106-2112.
22. [22] For the intermolecular version of this transformation upon N-acyl tetrahydropyridines, see: Matsumura Y, Terauchi J, Yamamoto T, Konno T, Shono T. Tetrahedron 1993;49:8503-8512.