Fluorous synthesis of hydantoins and thiohydantoins

Organic Letters

Volumn 5, Issue 14, 2003, Pages 2555-2558

  Zhang, Wei ^a   Lu, Yimin ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ESTER; HYDANTOIN DERIVATIVE; ISOCYANIC ACID DERIVATIVE; THIOHYDANTOIN DERIVATIVE; UREA DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; DRUG PURIFICATION; DRUG SYNTHESIS; REACTION ANALYSIS; SEPARATION TECHNIQUE; SOLID PHASE EXTRACTION;

HYDANTOINS; MAGNETIC RESONANCE SPECTROSCOPY; THIOHYDANTOINS;

EID: 0141854273     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034854a     Document Type: Article

References (46)

1. Selected references: (a) Ware, E. Chem. Rev. 1950, 46, 403. (b) Spinks, A.; Waring, W. S. Prog. Med. Chem. 1963, 3, 313. (c) Brouillete, W. J.; Jestkov, V. P.; Brown, M. L.; Akhtar, M. S.; DeLorey, T. M.; Brown, G. B. J. Med. Chem. 1994, 37, 3289. (d) Nefzi, A.; Giulianotti, M.; Truong, L.; Rattan, S.; Ostresh, J. M.; Houghten, R. A. J. Comput. Chem. 2002, 4, 175 and references therein.
2. Selected references: (a) Ware, E. Chem. Rev. 1950, 46, 403. (b) Spinks, A.; Waring, W. S. Prog. Med. Chem. 1963, 3, 313. (c) Brouillete, W. J.; Jestkov, V. P.; Brown, M. L.; Akhtar, M. S.; DeLorey, T. M.; Brown, G. B. J. Med. Chem. 1994, 37, 3289. (d) Nefzi, A.; Giulianotti, M.; Truong, L.; Rattan, S.; Ostresh, J. M.; Houghten, R. A. J. Comput. Chem. 2002, 4, 175 and references therein.
3. Selected references: (a) Ware, E. Chem. Rev. 1950, 46, 403. (b) Spinks, A.; Waring, W. S. Prog. Med. Chem. 1963, 3, 313. (c) Brouillete, W. J.; Jestkov, V. P.; Brown, M. L.; Akhtar, M. S.; DeLorey, T. M.; Brown, G. B. J. Med. Chem. 1994, 37, 3289. (d) Nefzi, A.; Giulianotti, M.; Truong, L.; Rattan, S.; Ostresh, J. M.; Houghten, R. A. J. Comput. Chem. 2002, 4, 175 and references therein.
4. Selected references: (a) Ware, E. Chem. Rev. 1950, 46, 403. (b) Spinks, A.; Waring, W. S. Prog. Med. Chem. 1963, 3, 313. (c) Brouillete, W. J.; Jestkov, V. P.; Brown, M. L.; Akhtar, M. S.; DeLorey, T. M.; Brown, G. B. J. Med. Chem. 1994, 37, 3289. (d) Nefzi, A.; Giulianotti, M.; Truong, L.; Rattan, S.; Ostresh, J. M.; Houghten, R. A. J. Comput. Chem. 2002, 4, 175 and references therein.
5. (a) Mizuno, T.; Kino, T.; Ito, T.; Miyata, T. Synth. Commun. 2000, 30, 1675.
6. (b) Mappes, C. J.; Pommer, E.-H.; Rentzea, C.; Zeeh, B. (BASF A.-G., Fed. Rep. Ger.). US Patent 4,198,423, 1980; Chem. Abstr. 1980, 93, 71784.
7. (b) Mappes, C. J.; Pommer, E.-H.; Rentzea, C.; Zeeh, B. (BASF A.-G., Fed. Rep. Ger.). US Patent 4,198,423, 1980; Chem. Abstr. 1980, 93, 71784.
8. (a) Mui, M.; Ganesan, A. J. Org. Chem. 1997, 62, 3230.
9. (b) Ohta, H.; Jikihara, T.; Wakabayashi, K.; Fujita, T. Pestic. Biochem. Physiol. 1980, 14, 153.
10. Recent references: (a) Sosa, A. C. B.; Yakushijin, K.; Horne, D. A. J. Org. Chem. 2002, 67, 4498. (b) Lamothe, M.; Lannuzel, M.; Perez, M. J. Com. Chem. 2002, 4, 73. (c) Kita, R.; Svec, F.; Frechet, J. M. J. J. Com. Chem. 2001, 3, 564. (d) Charton, J.; Delarue, S.; Vendeville, S.; Debreu-Fontaine, M.-A.; Mizzi, S.; Sergheraert, C. Tetrahedron Lett. 2001, 42, 7559. (e) Park, K.-H.; Kurt, M. J. Tetrahedron Lett. 2000, 41, 7409. (f) Dorwald, F. Z. Organic Synthesis on Solid Phase; Wiley-VCH: Weinheim, 2000; pp 363-366.
11. Recent references: (a) Sosa, A. C. B.; Yakushijin, K.; Horne, D. A. J. Org. Chem. 2002, 67, 4498. (b) Lamothe, M.; Lannuzel, M.; Perez, M. J. Com. Chem. 2002, 4, 73. (c) Kita, R.; Svec, F.; Frechet, J. M. J. J. Com. Chem. 2001, 3, 564. (d) Charton, J.; Delarue, S.; Vendeville, S.; Debreu-Fontaine, M.-A.; Mizzi, S.; Sergheraert, C. Tetrahedron Lett. 2001, 42, 7559. (e) Park, K.-H.; Kurt, M. J. Tetrahedron Lett. 2000, 41, 7409. (f) Dorwald, F. Z. Organic Synthesis on Solid Phase; Wiley-VCH: Weinheim, 2000; pp 363-366.
12. Recent references: (a) Sosa, A. C. B.; Yakushijin, K.; Horne, D. A. J. Org. Chem. 2002, 67, 4498. (b) Lamothe, M.; Lannuzel, M.; Perez, M. J. Com. Chem. 2002, 4, 73. (c) Kita, R.; Svec, F.; Frechet, J. M. J. J. Com. Chem. 2001, 3, 564. (d) Charton, J.; Delarue, S.; Vendeville, S.; Debreu-Fontaine, M.-A.; Mizzi, S.; Sergheraert, C. Tetrahedron Lett. 2001, 42, 7559. (e) Park, K.-H.; Kurt, M. J. Tetrahedron Lett. 2000, 41, 7409. (f) Dorwald, F. Z. Organic Synthesis on Solid Phase; Wiley-VCH: Weinheim, 2000; pp 363-366.
13. Recent references: (a) Sosa, A. C. B.; Yakushijin, K.; Horne, D. A. J. Org. Chem. 2002, 67, 4498. (b) Lamothe, M.; Lannuzel, M.; Perez, M. J. Com. Chem. 2002, 4, 73. (c) Kita, R.; Svec, F.; Frechet, J. M. J. J. Com. Chem. 2001, 3, 564. (d) Charton, J.; Delarue, S.; Vendeville, S.; Debreu-Fontaine, M.-A.; Mizzi, S.; Sergheraert, C. Tetrahedron Lett. 2001, 42, 7559. (e) Park, K.-H.; Kurt, M. J. Tetrahedron Lett. 2000, 41, 7409. (f) Dorwald, F. Z. Organic Synthesis on Solid Phase; Wiley-VCH: Weinheim, 2000; pp 363-366.
14. Recent references: (a) Sosa, A. C. B.; Yakushijin, K.; Horne, D. A. J. Org. Chem. 2002, 67, 4498. (b) Lamothe, M.; Lannuzel, M.; Perez, M. J. Com. Chem. 2002, 4, 73. (c) Kita, R.; Svec, F.; Frechet, J. M. J. J. Com. Chem. 2001, 3, 564. (d) Charton, J.; Delarue, S.; Vendeville, S.; Debreu-Fontaine, M.-A.; Mizzi, S.; Sergheraert, C. Tetrahedron Lett. 2001, 42, 7559. (e) Park, K.-H.; Kurt, M. J. Tetrahedron Lett. 2000, 41, 7409. (f) Dorwald, F. Z. Organic Synthesis on Solid Phase; Wiley-VCH: Weinheim, 2000; pp 363-366.
15. Recent references: (a) Sosa, A. C. B.; Yakushijin, K.; Horne, D. A. J. Org. Chem. 2002, 67, 4498. (b) Lamothe, M.; Lannuzel, M.; Perez, M. J. Com. Chem. 2002, 4, 73. (c) Kita, R.; Svec, F.; Frechet, J. M. J. J. Com. Chem. 2001, 3, 564. (d) Charton, J.; Delarue, S.; Vendeville, S.; Debreu-Fontaine, M.-A.; Mizzi, S.; Sergheraert, C. Tetrahedron Lett. 2001, 42, 7559. (e) Park, K.-H.; Kurt, M. J. Tetrahedron Lett. 2000, 41, 7409. (f) Dorwald, F. Z. Organic Synthesis on Solid Phase; Wiley-VCH: Weinheim, 2000; pp 363-366.
16. DeWitt, S. H.; Kiely, J. S.; Stankovic, C. J.; Schroeder, M. C.; Cody, D. M. R.; Pavia, M. R. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 6909.
17. Bräse, S.; Dahmen, S. In Handbook of Combinatorial Chemistry; Nicolaou, K. C., Hanko, R., Hartwig, W., Eds.; Wiley-VCH: Weinheim, 2002; Vol. 1, pp 59-169.
18. For general reviews, see (a) Zhang, W. Tetrahedron, 2003, 59, 4475. (b) Gladysz, J. A.; Curran, D. P. Tetrahedron 2002, 58, 3823. (c) Curran, D. P. In Stimulating Concepts in Chemistry; Stoddard, F., Reinhoudt, D., Shibasaki, M., Eds.; Wiley-VCH: New York, 2000; pp 25-37. (d) Curran, D. P. Angew. Chem., Int. Ed. 1998, 37, 1175.
19. For general reviews, see (a) Zhang, W. Tetrahedron, 2003, 59, 4475. (b) Gladysz, J. A.; Curran, D. P. Tetrahedron 2002, 58, 3823. (c) Curran, D. P. In Stimulating Concepts in Chemistry; Stoddard, F., Reinhoudt, D., Shibasaki, M., Eds.; Wiley-VCH: New York, 2000; pp 25-37. (d) Curran, D. P. Angew. Chem., Int. Ed. 1998, 37, 1175.
20. For general reviews, see (a) Zhang, W. Tetrahedron, 2003, 59, 4475. (b) Gladysz, J. A.; Curran, D. P. Tetrahedron 2002, 58, 3823. (c) Curran, D. P. In Stimulating Concepts in Chemistry; Stoddard, F., Reinhoudt, D., Shibasaki, M., Eds.; Wiley-VCH: New York, 2000; pp 25-37. (d) Curran, D. P. Angew. Chem., Int. Ed. 1998, 37, 1175.
21. For general reviews, see (a) Zhang, W. Tetrahedron, 2003, 59, 4475. (b) Gladysz, J. A.; Curran, D. P. Tetrahedron 2002, 58, 3823. (c) Curran, D. P. In Stimulating Concepts in Chemistry; Stoddard, F., Reinhoudt, D., Shibasaki, M., Eds.; Wiley-VCH: New York, 2000; pp 25-37. (d) Curran, D. P. Angew. Chem., Int. Ed. 1998, 37, 1175.
22. (a) Curran, D. P. Synlett 2001, 1488.
23. (b) Curran, D. P.; Oderaotoshi, Y. Tetrahedron 2001, 57, 5243.
24. (a) Dandapani, S.; Curran, D. P. Tetrahedron 2002, 58, 3855.
25. (b) Dobbs, A. McGregor-Johnson, C. Tetrahedron Lett. 2002, 43, 2807.
26. (c) Crich, D.; Neelamkavil, S. Tetrahedron 2002, 58, 3865.
27. (a) Zhang, W.; Chen, C. H.-T.; Nagashima, T. Tetrahedron Lett. 2003, 44, 2065.
28. (b) Zhang, W.; Curran, D. P.; Chen, C. H.-T. Tetrahedron 2002, 58, 3871.
29. (c) Lindsley, C. W.; Zhao, Z.; Leister, W. 2002, 43, 4225.
30. (a) Luo, Z. Y.; Williams, J.; Read, R. W.; Curran, D. P J. Org. Chem. 2001, 4261.
31. (b) Rover, S.; Wipf, P. Tetrahedron Lett. 1999, 40, 5667.
32. (a) Zhang, W. Org. Lett. 2003, 5, 1011.
33. (b) Chen, C.H.-T.; Zhang, W. Org. Lett. 2003, 5, 1015.
34. (a) Zhang, W.; Luo, Z.; Chen, C.H.-T.; Curran, D. P. J. Am. Chem. Soc. 2002, 124, 10443.
35. (b) Zhang, Q.; Rivkin, A.; Curran, D. P. J. Am. Chem. Soc. 2002, 124, 5774.
36. (c) Luo, Z. Y.; Zhang, Q. S.; Oderaotoshi, Y.; Curran, D. P. Science 2001, 291, 1766.
37. (a) Wipf, P.; Methot, J.-L. Org. Lett. 1999, 1, 1253.
38. (b) Schwinn, D. Bannwarth, W. Helv. Chim. Acta 2002, 85, 255.
39. (c) For a fluorous solvent-free separation, see: Schwinn, D.; Glatz, H.; Bannwarth, W. Helv. Chim. Acta 2003, 86, 188.
40. 2O followed by 20 mL of MeOH. The MeOH fraction was concentrated to give desired product 2 in 80-90% yields.
41. For more information about F-SPE, see: Fluourous Technologies, Inc. http://fluorous.com/download/fspe.pdf.
42. 2OH are available from Fluourous Technologies, Inc.: www.fluorous.com.
43. Lindsley, C. W.; Zhao, Z.; Leister, W. H. Strauss, K. A. Tetrahedron Lett. 2002, 43, 6319.
44. + + H).
45. Gallo, R.; Roussel, C.; Berg, U. Adv. Hetercycl. Chem 1988, 43, 174.
46. Curran, D. P.; Amatore, M.; Guthrie, D.; Campbell, M.; Go, E.; Luo, Z. J. Org. Chem. 2003, ASAP article.