Base-promoted solid-phase synthesis of substituted hydantoins and thiohydantoins

Journal of Organic Chemistry

Volumn 62, Issue 17, 1997, Pages 6090-6092

  Matthews, Jay ^a   Rivero, Ralph A ^a  

^a R W JOHNSON PHARMACEUTICAL RES I   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

HYDANTOIN; HYDANTOIN DERIVATIVE; THIOHYDANTOIN DERIVATIVE;

ARTICLE; CHEMICAL MODIFICATION; DRUG SYNTHESIS; SOLID PHASE EXTRACTION;

EID: 0030876296     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970521d     Document Type: Article

References (25)

1. (a) Thompson, L. A.; Ellman, J. A. Chem. Rev. 1996, 96, 555.
2. (b) Gallop, M. A.; Barrett, R. W.; Dower, W. J.; Fodor, S. P. A.; Gordon, E. M. J. Med. Chem. 1994, 37, 1233.
3. (a) Boojamra, C. G.; Burow, K. M.; Ellman, J. A. J. Org. Chem. 1995, 60, 5742.
4. (b) Mayer, J. P.; Zhang, J.; Bjergarde, K.; Lenz, D. M.; Gaudini, J. J. Tetrahedron Lett. 1996, 37, 8081.
5. (c) Bunin, B. A.; Plunkett, M. J.; Ellman, J. A. Proc. Natl. Acad. Sci. U.S.A. 1994, 91, 4708.
6. (d) Plunkett, M. J.; Ellman, J. A. J. Am. Chem. Soc. 1995, 117, 3306.
7. (a) Gordon, D. W.; Steele, J. Bioorg. Med. Chem. Lett. 1995, 5, 47.
8. (b) Terrett, N. K.; Bojanic, D.; Brown, D.; Bungay, P. J.; Gardner, M.; Gordon, D. W.; Mayes, C. J.; Steele, J. Bioorg. Med. Chem. Lett. 1995, 5, 917.
9. Dankwardt, S. M.; Newman, S. R.; Drstenansky, J. L. Tetrahedron Lett. 1995, 36, 4923.
10. Panek, J. S.; Zhu, B. Tetrahedron Lett. 1996, 37, 8151.
11. (a) Dressman, B. A.; Spangle, L. A.; Kaldor, S. W. Tetrahedron Lett. 1996, 37, 937.
12. (b) DeWitt, S. H.; Kiely, J. S.; Stankovic, M. C.; Shroeder, D. M.; Reynolds, C.; Pavia, M. R. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 6909.
13. (c) Hanessian, S.; Yang, R. Y. Tetrahedron Lett. 1996, 37, 5835.
14. Carrera, G. M., Jr.; Garvey, D. S. J. Heterocycl. Chem. 1992, 29, 847.
15. Coudert, P.; Rubar, C.; Couguelet, J. M.; Bastide, J.; Bastide, P. Pharm. Acta Helv. 1991, 66, 155.
16. Szardenings, A. K.; Burkoth, T. S.; Look, G. C., Campbell, D. A. J. Org. Chem. 1996, 61, 6720.
17. (b) Green, J. J. Org. Chem. 1995, 60, 4287.
18. (c) Krchnak, V.; Weichsel, A. S.; Cabel, D.; Flegelova, Z.; Lebl, M. Mol. Diversity 1995, 1, 149.
19. (d) Bray, A. M.; Chiefari, D. S.; Valerio, M.; Maeji, N. J. Tetrahedron Lett. 1995, 36, 5081.
20. (e) Chan, W. C.; Mellor, S. L. J. Chem. Soc., Chem. Commun. 1995, 1475.
21. (a) Smith, J.; Liras, J. L.; Schneider, S. E.; Anslyn, E. V. J. Org. Chem. 1996, 61, 8811.
22. (b) Sim, M. M.; Ganesan, A. J. Org. Chem. 1997, 61, 3230.
23. Kaldor, S. W.; Fritz, J. E.; Tang, J.; McKinney, E. R. Bioorg. Med. Chem. Let. 1996, 24, 3041.
24. Also suggestive of the product's con figuration al integrity was the lack of diastereomer formation for the isoleucine analogs as detected by NMR, TLC, and HPLC. For example, the NMR spectrum of compound 2e contained a clean doublet at 4.25 ppm for the methine proton of the hydantoin ring.
25. In the case of 1f, the reaction of the resin-bound secondary amine with the isocyanate was performed at room temperature for 3 days.