Preparation of 3-(4-pyridinylamino)-1,2-benzisoxazoles via a nucleophilic aromatic substitution reaction

Tetrahedron Letters

Volumn 37, Issue 7, 1996, Pages 995-998

  Fink, David M ^a   Kurys, Barbara E ^a  

^a SANOFI   (France)

Author keywords

[No Author keywords available]

Indexed keywords

3 (4 PYRIDYLAMINO) 1,2 BENZISOXAZOLE DERIVATIVE; ISOXAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0030064160     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(95)02361-5     Document Type: Article

References (14)

1. Boshagen, H.; Schraufstatter, E. Angew. Chem. 1960, 1000.
2. Shutske, G. M.; Kapples, K. J. J. Het. Chem. 1989, 26, 1293-1298.
3. Palermo, M. G. Abstracts of the 211th American Chemical Society National Meeting 1995, ORGN 246, abstract.
4. Boshagen, H. Chem. Ber. 1967, 100, 3326-3330.
5. Alkylation of 3-amino-1,2-benzisoxazole with 4-chloropyridine did provide 1 (X=H, R=H) in 26% yield. Shutske, G. M. and Tomer, J. D. personal communication.
6. Wunsch, K.-H.; Boulton, A. J. In Advances in Heterocyclic Chemistry; Katritzky, A. R.; Boulton, A. J. Eds.; Academic Press: New York, 1967; pp 277-379.
7. Gozlan, H.; Michelot, R.; Riche, C.; Rips, R. Tetrahedron 1977, 33, 2535-2542.
8. Exner, O.; Jehlicka, V.; Dondoni, A.; Boicelli, A. C. J. Chem. Soc. Perkin Trans. II 1974, 567-571.
9. Dignam, K. J.; Hegarty, A. F.; Quain, P. L. J. Chem. Soc. Perkin Trans. II 1977, 1457-1462.
10. Phosphorus pentachloride was the reagent of choice and was necessary for substrates containing an electron withdrawing group on the aromatic ring (examples 6-9).
11. 6
12. 1H NMR, mass and IR spectra.
13. This example was not run at ambient temperature, although based on the results with the trifluoromethyl substituent it may have worked at this temperature.
14. In some cases the trimethylsilyl group was not fully removed under the reaction conditions. Stirring the reaction mixture with 10% HCl completed the desilylation in these cases.