Solid-phase synthesis of N-hydroxyindoles and benzo[c]isoxazoles by C-arylation of substituted acetonitriles and 1,3-dicarbonyl compounds with polystyrene-bound aryl fluorides

Tetrahedron Letters

Volumn 40, Issue 31, 1999, Pages 5799-5802

  Stephensen, Henrik ^a   Zaragoza, Florencio ^a  

^a NOVO NORDISK A S   (Denmark)

Author keywords

Benzisoxazoles; C arylation; Indoles; Solid phase synthesis

Indexed keywords

ACETONITRILE DERIVATIVE; CARBONYL DERIVATIVE; INDOLE DERIVATIVE; ISOXAZOLE DERIVATIVE; NITROBENZOIC ACID DERIVATIVE; POLYSTYRENE; RESIN; TIN CHLORIDE;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; CROSS LINKING; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS; REDUCTION; SOLID; STRUCTURE ANALYSIS;

EID: 0033618318     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01117-X     Document Type: Article

References (20)

1. (a) Stephensen, H.; Zaragoza, F. J. Org. Chem. 1999, 64, 2555-2557.
2. (b) Stephensen, H.; Zaragoza, F. J. Org. Chem. 1997, 62, 6096-6097.
3. (c) Zaragoza, F. Tetrahedron Lett. 1997, 38, 7291-7294.
4. (d) Zaragoza, F.; Petersen, S. V. Tetrahedron 1996, 52, 10823-10826.
5. (a) Fortes, I. T.; Morgan, H. K. A.; Thompson, M. Synth. Commun. 1996, 26, 745-754.
6. (b) Uhle, F. C. J. Am. Chem. Soc. 1949, 71, 761-766.
7. (c) Bonjoch, J.; Quirante, J.; Linares, A.; Bosch, J. Heterocycles 1988, 27, 2883-2890.
8. (d) Modi, S. P.; Oglesby, R. C.; Archer, S. Org. Synth. 1993, 72, 125-134.
9. (e) Snyder, H. R.; Merica, E. P.; Force, C. G.; White, E. G. J. Am. Chem. Soc. 1958, 80, 4622-4625.
10. (f) Walker, G. N. J. Am. Chem. Soc. 1955, 77, 3844-3850.
11. (g) Munshi, K. L.; Kohl, H.; de Souza, N. J. J. Heterocycl. Chem. 1977, 14, 1145-1146.
12. Morales, G. A.; Corbett, J. W.; Degrado, W. F. J. Org. Chem. 1998, 63, 1172-1177.
13. 1H NMR with an internal reference. Yields of products 3 and 6 were calculated on the basis of this loading.
14. 4 (233.23): C, 61.80; H, 4.75; N, 6.01. Found: C, 61.61; H, 4.75; N, 5.78.
15. Ruhland, T.; Künzer, H. Tetrahedron Lett. 1996, 37, 2757-2760.
16. Phillips, G. B.; Wei, G. P. Tetrahedron Lett. 1996, 37, 4887-4890.
17. Kulp, S. S.; McGee, M. J. J. Org. Chem. 1983, 48, 4097-4098.
18. Donetti, A.; Boniardi, O.; Ezhaya, A. Synthesis 1980, 1009-1011.
19. Korte, F.; Behner, O. Liebigs Ann. Chem. 1959, 621, 51-57.
20. 2O (514.46): C, 51.36; H, 4.90; N, 10.89. Found: C, 51.37; H, 4.81; N, 10.81.