Iodobenzene diacetate-promoted N-N and N-O bond formation for pyrazolo- and isoxazolopyrimidine syntheses

Heterocycles

Volumn 79, Issue C, 2009, Pages 669-680

  Monguchi, Yasunari ^a   Hattori, Kazuyuki ^a   Maegawa, Tomohiro ^a   Hirota, Kosaku ^a   Sajiki, Hironao ^a  

^a GIFU PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

Iodobenzene Diacetate; Isoxazole; N N Bond Formation; N O Bond Formation; Pyrazole

Indexed keywords

EID: 67651123126     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-08-S(D)34     Document Type: Article

References (59)

1. Robins R.K. J. Am. Chem. Soc. 78 (1956) 784
2. Feigelson P., Davidson J.D., and Robins R.K. J. Biol. Chem. 226 (1957) 993
3. Kobayashi S. Chem. Pharm. Bull. 21 (1973) 941
4. Robins R.K., Revankar G.R., O'Brien D.E., Springer R.H., Novinson T., Albert A., Senga K., Miller J.P., and Streeter D.G. J. Heterocycl. Chem. 22 (1985) 601
5. Elnagdi M.H., and Elmoghayar M.R.H. In: Katritzky A.R. (Ed). Advances in Heterocyclic Chemistry: Chemistry of Pyrazolopyrimidines Vol. 41 (1987), Academic Press, Orlando 319-376
6. Greehill J.V. In: Katritzky A.R., and Rees C.W. (Eds). Comprehensive Heterocyclic Chemistry: Pyrazoles with Fused Six-menmbered Heterocyclic Rings Vol. 5 (1984), Pergamon Press, Oxford 305-343
7. Robins R.K. J. Med. Chem. 7 (1964) 186
8. Petrie III C.R., Cottam H.B., McKernan P.A., Robins R.K., and Revankar G.H. J. Med. Chem. 28 (1985) 1010
9. Hanke J.H., Gardner J.P., Dow R.L., Changelian P.S., Brissette W.H., Weringer E.J., Pollok B.A., and Connelly P.A. J. Biol. Chem. 271 (1996) 695
10. Maruyama T., Yamamoto Y., Shimizu A., Masuda H., Sakai N., Sakurai R., Asada H., and Yoshimura Y. Biol. Reprod. 70 (2004) 214
11. Carraro F., Pucci A., Naldini A., Schenone S., Bruno O., Ranise A., Bondavalli F., Brullo C., Fossa P., Menozzi G., Mosti L., Manetti F., and Botta M. J. Med. Chem. 47 (2004) 1596
12. Carraro F., Naldini A., Pucci A., Locatelli G.A., Maga G., Schenone S., Bruno O., Ranise A., Bondavalli F., Brullo C., Fossa P., Menozzi G., Mosti L., Modugno M., Tintori C., Manetti F., and Botta M. J. Med. Chem. 49 (2006) 1549
13. Manetti F., Santucci A., Locatelli G.A., Maga G., Spreafico A., Serchi T., Orlandini M., Bernardini G., Caradonna N.P., Spallarossa A., Brullo C., Schenone S., Bruno O., Ranise A., Bondavalli F., Hoffmann O., Bologna M., Angelucci A., and Botta M. J. Med. Chem. 50 (2007) 5579
14. Traxler P., and Furet P. Pharmacol. Ther. 82 (1999) 195
15. Manetti F., Brullo C., Magnani M., Mosci F., Chelli B., Crespan E., Schenone S., Naldini A., Bruno O., Trincavelli M.L., Maga G., Carraro F., Martini C., Bondavalli F., and Botta M. J. Med. Chem. 51 (2008) 1252
16. Das J., Moquin R.V., Pitt S., Zhang R., Shen D.R., McIntyre K.W., Gillooly K., Doweyko A.M., Sack J.S., Zhang H., Kiefer S.E., Kish K., McKinnon M., Barrish J.C., Dodd J.H., Schieven G..L., and Leftheris K. Bioorg. Med. Chem. Lett. 18 (2008) 2652
17. Devesa I., Alcaraz M.J., Riguera R., and Ferrándiz M.L. Eur. J. Pharmacol 488 (2004) 225
18. Ali A., Taylor G.E., Ellsworth K., Harris G., Painter R., Silver L.L., and Young K. J. Med. Chem. 46 (2003) 1824
19. Zhang Y., Jin G., Illarionov B., Bacher A., Fischer M., and Cushman M. J. Org. Chem. 72 (2007) 7176
20. Gillespie R.J., Cli I.A., Dawson C.E., Dourish C.T., Gaur S., Jordan A.M., Knight A.R., Lerpiniere J., Misra A., Pratt R.M., Ro J., Stratton G.C., Upton R., Weiss S.M., and Williamson D.S. Bioorg. Med. Chem. Lett. 18 (2008) 2924
21. Liu H., He X., Choi H.-S., Yang K., Woodmansee D., Wang Z., Ellis D.A., Wu B., He Y., and Nguyen T.N. (Irm LLC, Bermuda), PCT Int. Appl., WO2006047516. Chem. Abstr. 144 (2006) 450725
22. Senda S., Hirota K., and Yang G.-N. Chem. Pharm. Bull. 20 (1972) 391
23. For example. Higashino T., Iwai Y., and Hayashi E. Chem. Pharm. Bull. 24 (1976) 3120
24. Madroñero R., and Vega S. Synthesis 1 (1987) 628
25. Garín J., Loscertales M.P., Meléndez E., Merchán F.L., Rodriguez R., and Tejero T. Heterocycles 26 (1987) 1303
26. Molina P., Argues A., and Vinader M.V. Tetrahedron Lett. 28 (1987) 4451
27. Molina P., Argues A., Vinader M.V., Becher J., and Brondum K. J. Org. Chem. 53 (1988) 4654
28. Hosmane R.S., and Lim B.B. Synthesis 1 (1988) 242
29. Anderson J.D., Cottam H.B., Larson S.B., Nord L.D., Revankar G.R., and Robins R.K. J. Heterocycl. Chem. 27 (1990) 439
30. Molina P., Argues A., and Vinader M.V. Synthesis 1 (1990) 469
31. Guccione S., Scolaro L.M., and Russo F. J. Heterocycl. Chem. 33 (1996) 459
32. For example. Senda S., Hirota K., and Yang G.-N. Chem. Pharm. Bull. 20 (1972) 399
33. Senga K., Kanamori Y., Kanazawa H., and Nishigaki S. Synthesis (1977) 176
34. Yoneda F., Nagamatsu T., and Nagamura T. Chem. Soc. Perkin Trans. (1977) 765
35. Senga K., Kanamori Y., Kanazawa H., and Nishigaki S. J. Heterocycl. Chem. 15 (1978) 359
36. Mátyus P., Sohár P., and Wamhoff H. Heterocycles 22 (1984) 513
37. El-Reedy A.M., Ali A.S., and Ayyad A.O. J. Heterocycl. Chem. 26 (1989) 313
38. Bhuyan P., Boruah R.C., and Sandhu J.S. J. Org. Chem. 55 (1990) 568
39. Neidlein R., and Wang Z. Heterocycles 45 (1997) 1509
40. Preliminary results were reported as a communication. Sajiki H., Hattorf K., Sako M., and Hirota K. Synlett (1997) 1409
41. Marumoto R., and Furukawa Y. Chem. Pharm. Bull. 25 (1977) 2974
42. Nishigaki S., Kanamori Y., and Senga K. Chem. Pharm. Bull. 26 (1978) 2497
43. Yoneda F., Yano T., Higuchi M., and Koshiro A. Chem. Lett. (1978) 155
44. Hirota K., Maruhashi K., Asao T., Kitamura N., Maki Y., and Senda S. Chem. Pharm. Bull. 31 (1983) 3959
45. Tinh D.V., and Stadlbauer W. J. Heterocycl. Chem. 33 (1966) 1025
46. Matsumoto N., and Takahashi M. Tetrahedron 58 (2002) 10073
47. Stang P.J., and Zhdankin V.V. Chem. Rev. 96 (1996) 1123
48. Wirth T., and Hirt U.H. Synthesis (1999) 1271
49. Kotali A., and Harris P.A. J. Heterocycl. Chem. 33 (1996) 605
50. Correa A., Tellitu I., Domínguez E., and SanMartin R. J. Org. Chem. 71 (2006) 3501
51. Prakash O., Saini R.K., Singh S.P., and Varma R.S. Tetrahedron Lett. 38 (1997) 3147
52. Reddy A.C.S., Narsaiah B., and Venkataratnam R.V. Synth. Commun. 27 (1997) 2217
53. Hirota K., Kitade Y., Sajiki H., and Maki Y. Synthesis (1984) 589
54. Hirota K., Kubo K., Sajiki H., Kitade Y., Sako M., and Maki Y. J. Org. Chem. 62 (1997) 2999
55. The cyclization precursors 2a and 2h could also be obtained by the reaction of the 5-foymyl- or 5-thioformyl-6-amino-1,3-dimethyluracil derivatives with primary amines. Hirota K., Kubo K., and Sajiki H. Chem. Pharm. Bull. 45 (1997) 542
56. Ford G.P., and Scribner J.D. J. Am. Chem. Soc. 103 (1981) 4281
57. Ohwada A., Nara S., Sakamoto T., and Kikugawa Y. J. Chem. Soc. Perkin Trans. 1 (2001) 3064
58. Kikugawa Y., Nagashima A., Sakamoto T., Miyazawa E., and Shiiya M. J. Org. Chem. 68 (2003) 6739
59. Clark J., and Morton M.S. J. Chem. Soc. Perkin Trans. 1 (1974) 1812