Directed lithiation of N-(tert-butoxycarbonyl)aminoisoxazole: Synthesis of 4-substituted aminoisoxazoles

Tetrahedron Letters

Volumn 37, Issue 19, 1996, Pages 3339-3342

  Konoike, Toshiro ^a   Kanda, Yasuhiko ^a   Araki, Yoshitaka ^a  

^a SHIONOGI AND CO LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ISOXAZOLE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; REACTION ANALYSIS; TECHNIQUE;

EID: 0029880765     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00476-5     Document Type: Article

References (23)

1. Kano, H; Ogata, K. Ann. Rep. Shionogi Res. Lab. 1957, 7, 1. See C.A. 1957, 51, 17889.
2. Kano, H; Ogata, K. Ann. Rep. Shionogi Res. Lab. 1957, 7, 1. See C.A. 1957, 51, 17889.
3. Stein, P. D.; Hunt, J. T.; Floyd, D. M.; Moreland, S.; Dickinson, K. E. J.; Mitchell, C.; Liu, E. C. -K.; Webb, M. L.; Murugesan, N.; Dickey, J.; McMullen, D.; Zhang, R.; Lee, V. G.; Serafino, R.; Delaney, C.; Schaeffer, T. R.; Kozlowski, M. J. Med. Chem. 1994, 37, 330.
4. For an extensive review of directed metallation chemistry, see Snieckus, V. Chem. Rev. 1990, 90, 879.
5. For a review of metallation of isoxazoles, see Iddon, B. Heterocycles 1994, 37, 1263.
6. Alberola, A.; Calvo, L.; Rodríguez, T. R.; Sañudo, C. J. Heterocyclic Chem. 1992, 29, 445. Micetich, R. G.; Shaw, C. C.; Hall, T. W.; Spevak, P.; Bains, B. K. Heterocycles 1985, 23, 585. Oster, T. A.; Harris, T. M. J. Org. Chem. 1983, 48, 4307. Bowden, K.; Crank, G.; Ross, W. J. J. Chem. Soc. (C). 1968, 172. Gainer, J.; Howarth, G. A.; Hoyle, W.; Roberts, S. M.; Suschitzky, H. J. Chem. Soc. Perkin I, 1976, 994.
7. Alberola, A.; Calvo, L.; Rodríguez, T. R.; Sañudo, C. J. Heterocyclic Chem. 1992, 29, 445. Micetich, R. G.; Shaw, C. C.; Hall, T. W.; Spevak, P.; Bains, B. K. Heterocycles 1985, 23, 585. Oster, T. A.; Harris, T. M. J. Org. Chem. 1983, 48, 4307. Bowden, K.; Crank, G.; Ross, W. J. J. Chem. Soc. (C). 1968, 172. Gainer, J.; Howarth, G. A.; Hoyle, W.; Roberts, S. M.; Suschitzky, H. J. Chem. Soc. Perkin I, 1976, 994.
8. Alberola, A.; Calvo, L.; Rodríguez, T. R.; Sañudo, C. J. Heterocyclic Chem. 1992, 29, 445. Micetich, R. G.; Shaw, C. C.; Hall, T. W.; Spevak, P.; Bains, B. K. Heterocycles 1985, 23, 585. Oster, T. A.; Harris, T. M. J. Org. Chem. 1983, 48, 4307. Bowden, K.; Crank, G.; Ross, W. J. J. Chem. Soc. (C). 1968, 172. Gainer, J.; Howarth, G. A.; Hoyle, W.; Roberts, S. M.; Suschitzky, H. J. Chem. Soc. Perkin I, 1976, 994.
9. Alberola, A.; Calvo, L.; Rodríguez, T. R.; Sañudo, C. J. Heterocyclic Chem. 1992, 29, 445. Micetich, R. G.; Shaw, C. C.; Hall, T. W.; Spevak, P.; Bains, B. K. Heterocycles 1985, 23, 585. Oster, T. A.; Harris, T. M. J. Org. Chem. 1983, 48, 4307. Bowden, K.; Crank, G.; Ross, W. J. J. Chem. Soc. (C). 1968, 172. Gainer, J.; Howarth, G. A.; Hoyle, W.; Roberts, S. M.; Suschitzky, H. J. Chem. Soc. Perkin I, 1976, 994.
10. Alberola, A.; Calvo, L.; Rodríguez, T. R.; Sañudo, C. J. Heterocyclic Chem. 1992, 29, 445. Micetich, R. G.; Shaw, C. C.; Hall, T. W.; Spevak, P.; Bains, B. K. Heterocycles 1985, 23, 585. Oster, T. A.; Harris, T. M. J. Org. Chem. 1983, 48, 4307. Bowden, K.; Crank, G.; Ross, W. J. J. Chem. Soc. (C). 1968, 172. Gainer, J.; Howarth, G. A.; Hoyle, W.; Roberts, S. M.; Suschitzky, H. J. Chem. Soc. Perkin I, 1976, 994.
11. Kalish, R.; Broger, E.; Field, G. F.; Anton, T.; Steppe, T. V.; Sternbach, L. H. J. Heterocyclic Chem. 1975, 12, 49. Antequera, T.; Ramos, V.; Torroba, T. Heterocycles 1986, 24, 3203. Alberola, A.; Serrano, A. P.; Rodríguez, M. T. R.; Orozco, C. Heterocycles 1989, 29, 667.
12. Kalish, R.; Broger, E.; Field, G. F.; Anton, T.; Steppe, T. V.; Sternbach, L. H. J. Heterocyclic Chem. 1975, 12, 49. Antequera, T.; Ramos, V.; Torroba, T. Heterocycles 1986, 24, 3203. Alberola, A.; Serrano, A. P.; Rodríguez, M. T. R.; Orozco, C. Heterocycles 1989, 29, 667.
13. Kalish, R.; Broger, E.; Field, G. F.; Anton, T.; Steppe, T. V.; Sternbach, L. H. J. Heterocyclic Chem. 1975, 12, 49. Antequera, T.; Ramos, V.; Torroba, T. Heterocycles 1986, 24, 3203. Alberola, A.; Serrano, A. P.; Rodríguez, M. T. R.; Orozco, C. Heterocycles 1989, 29, 667.
14. For papers on application of Boc-amino directed lithiation of benzene and pyridine, see Muchowski, J. M.; Venuti, M. C. J. Org. Chem. 1980, 45, 4798. Salituro, F. G.; McDonald, I. A. J. Org. Chem. 1988, 53, 6138. Kelly, T. A.; Patel, U. R. J. Org. Chem. 1995, 60, 1875.
15. For papers on application of Boc-amino directed lithiation of benzene and pyridine, see Muchowski, J. M.; Venuti, M. C. J. Org. Chem. 1980, 45, 4798. Salituro, F. G.; McDonald, I. A. J. Org. Chem. 1988, 53, 6138. Kelly, T. A.; Patel, U. R. J. Org. Chem. 1995, 60, 1875.
16. For papers on application of Boc-amino directed lithiation of benzene and pyridine, see Muchowski, J. M.; Venuti, M. C. J. Org. Chem. 1980, 45, 4798. Salituro, F. G.; McDonald, I. A. J. Org. Chem. 1988, 53, 6138. Kelly, T. A.; Patel, U. R. J. Org. Chem. 1995, 60, 1875.
17. 3: C, 54.53; H, 7.12; N, 14.13. Found: C, 54.40; H, 7.05; N, 14.14. formula represented
18. 13C-NMR, IR, mass spectra and/or elemental analysis were obtained for all the new compounds.
19. The isoxazolylacetic acid was obtained by the reaction with carbon dioxide. formula represented
20. Zhang, P.; Gawley, R. E. J. Org. Chem. 1993, 58, 3223. In the alkylation with methyl iodide, the mandelamide was obtained with the desired methylated isoxazole as shown below. formula represented
21. Hoppe, I.; Schöllkopf, U. Liebigs Ann. Chem. 1979, 219. Nesi, R.; Ricci, A.; Taddei, M.; Tedeschi, P.; Seconi, G. J. Organomet. Chem. 1980, 195, 275. We were unable to isolate and characterize fragments of the isoxazole.
22. Hoppe, I.; Schöllkopf, U. Liebigs Ann. Chem. 1979, 219. Nesi, R.; Ricci, A.; Taddei, M.; Tedeschi, P.; Seconi, G. J. Organomet. Chem. 1980, 195, 275. We were unable to isolate and characterize fragments of the isoxazole.
23. 5-(Boc-amino)-3-methylisoxazole 9 was prepared in a similar way to the preparation of 4.