1,4-Diazabicyclo[2.2.2]octane (DABCO) as an efficient reagent for the synthesis of isoxazole derivatives from primary nitro compounds and dipolarophiles: The role of the base

European Journal of Organic Chemistry

Volumn , Issue 21, 2006, Pages 4852-4860

  Cecchi, Luca ^a   De Sarlo, Francesco ^a   Machetti, Fabrizio ^a  

^a UNIVERSITY OF FLORENCE   (Italy)

Author keywords

Cycloaddition; DABCO; Heterocycles; Nitro compounds

Indexed keywords

EID: 33750876849     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200600475     Document Type: Article

References (73)

1. T. Mukaiyama, T. Hoshino, J. Am. Chem. Soc. 1960, 82, 5339-5342.
2. a) P. Caramella, P. Grünanger in 1,3-Dipolar Cycloaddition Chemistry (Ed.: A. Padwa), Wiley, New York, 1984;
3. b) K. B. G. Torsell, Nitrite Oxides, Nitrones and Nitronates in Organic Synthesis, VCH, Weinheim, 1988;
4. c) J. Mulzer, Organic Synthesis Highlights, VCH, Weinheim, 1991;
5. d) V. Jäger, P. A. Colinas in Synthetic Applications of 1,3-Dipolar Cycloaddition Chemistry Toward Heterocycles and Natural Products (Eds.: A. Padwa, W. H. Pearson), Wiley, New Jersey, 2003, p. 368.
6. For example, see V. A. Tartakovskii, I. E. Chlenov, S. S. Smagin, S. S. Novikov, Bull. Acad. Sci USSR Div. Chem. Sci. (Engl. Transl.) 1964, 549;
7. Izv. Akad. Nauk. SSSR, Ser Khim. 1964, 3, 583-584;
8. Chem. Abstr. 1964, 60, 90803.
9. K. B. G. Torsell, O. Zeuthen, Acta Chem. Scand. Ser. B 1978, 32, 118-124.
10. I. N. N. Namboothiri, A. Hassner, H. E. Gottlieb, J. Org. Chem. 1997, 62, 485-492.
11. E. W. Colvin, A. K. Beck, B. Bastani, D. Seebach, Y. Kai, D. Dunitz, Helv. Chim. Acta 1980, 63, 697-710.
12. 1,4-Phenylene diisocyanate: V. Jäger, I. Müller, Tetrahedron 1985, 41, 3519-3528.
13. Diketene: S. Tsushima, T. Tsujikawa, O. Aki, Jpn. Tokkyo Koho JP 43024902, 1968; Chem. Abstr. 1969, 70, 87344.
14. Phosphorus oxychloride: J. E. McMurry, Org. Synth. 1973, 53, 59-62.
15. Acetic anhydride/sodium acetate: A. Mckillop, R. J. Kobylecki, Tetrahedron 1974, 30, 1365-1371.
16. Acetyl chloride: K. Harada, E. Kaji, S. Sen, Chem. Pharm. Bull. 1980, 28, 3296-3303.
17. Thionyl chloride: Y.-J. Chen, C.-N. Li, J. Chin. Chem. Soc. 1993, 40, 203-207;
18. Chem. Abstr. 1993, 119, 180693.
19. N,N-Diethylaminosulfur trifluoride (DAST) and Methyl N- (triethylammoniosulfonyl)carbamate (Burgess salt): N. Maugein, A. Wagner, C. Mioskowsi, Tetrahedron Lett. 1997, 38, 1547-1550.
20. [23]
21. I. V. Vigalok, I.E. Moisak, N. V. Svetlakov, Chem. Heterocycl. Compd. 1969, 5, 133;
22. Khim. Geterotsikl. Soedin. 1969, 5, 175;
23. Chem. Abstr. 1969, 71, 3330.
24. T. Shimizu, Y. Hayashi, K. Teramura, Bull. Chem. Soc. Jpn. 1984, 57, 2531-2534.
25. M. G. Leslie-Smith, R. M. Paton, N. Webb, Tetrahedron Lett. 1994, 55, 9251-9254.
26. E. Kaji, K. Harada, S. Zen, Chem. Pharm. Bull. 1978, 26, 3254-3256.
27. T. Shimizu, Y. Hayashi, H. Shibafuchi, K. Teramura, Bull. Chem. Soc. Jpn. 1986, 59, 2827-2831.
28. Y. Basel, A. Hassner, Synthesis 1997, 309-312.
29. S. D. Nelson, D. J. Kasparian, W. F. Trager, J. Org. Chem. 1972, 37, 2686-2688.
30. A. Rahman, N. Razzaq, A. Jabbar, Pak. J. Sci. Res. 1978, 30, 91-94;
31. Chem. Abstr. 1979, 90, 203967.
32. L. Cecchi, F. De Sarlo, F. Machetti, Tetrahedron Lett. 2005, 46, 7877-7879.
33. L. Cecchi, F. De Sarlo, C. Faggi, F. Machetti, Eur. J. Org. Chem. 2006, 3016-3020.
34. R. Ballini, G. Bosica, D. Fiorini, Tetrahedron 2003, 59, 1143-1145.
35. P. Beltrame, G. Gelli, A. Loi, Gazz. Chim. Ital. 1980, 110, 491-494.
36. V. Frenna, N. Vivona, G. Consiglio, D. Spinelli, J. Chem. Soc., Perkin Trans. 2 1985, 1865-1868.
37. S. Bruckenstein, I. M. Kolthoff, J. Am. Chem. Soc. 1956, 78, 2974-2979.
38. E. A. Castro, M. Cubillos, J. G. Santos, J. Org. Chem. 2004, 69, 4802-4807.
39. F. Hibbert, J. Chem. Soc., Perkin Trans. 2 1974, 1862-1866.
40. E. Marquis, J. Graton, M. Berthelot, A. Planchat, C. Laurence, Can. J. Chem. 2004, 82, 1413-1422.
41. G. Ivanova, E. Bratovanova, D. Petkov,J. Pept. Sci. 2002, 8, 8-12.
42. P. K. Bruice, J. Am. Chem. Soc. 1983, 105, 4982-4996.
43. A. H. Lewin, G. Sun, L. Fudala, H. Navarro, L.-M. Zhou, P. Popik, A. Faynsteyn, P. Skolnick, J. Med. Chem. 1998, 41, 988-995.
44. J. P. Street, K. I. Skorey, R. S. Brown, R. G. Ball, J. Am. Chem. Soc. 1985, 107, 7669-7679.
45. C. S. Cassidy, L. A. Reinhardt, W. W. Cleland, A. P. Frey, J. Chem. Soc., Perkin Trans. 2 1999, 635-641.
46. D. H. Aue, H. M. Webb, D. W. R. Davidson, P. Toure, H. P. Hopkins, S. P. Moulik, D. V. Jahagirdar, J. Am. Chem. Soc. 1991, 113, 1770-1780.
47. A. Albert, R. Goldacre, J. Phillips, J. Chem. Soc. 1948, 2240-2246.
48. A. P. Cooney, M. R. Crampton, P. Golding, J. Chem. Soc., Perkin Trans. 2 1986, 835-840.
49. P. Wiczling, M. J. Markuszewski, R. Kalisan, Anal. Chem. 2004, 76, 3069-3077.
50. T. Pineda, J. M. Sevilla, M. Blazquez, L. J. Nunez-Vergara, J. A. Squella, M. Dominguez, Gazz. Chim. Ital. 1993, 123, 623-628.
51. A. Jarczewski, C. D. Hubbard, J. Mol. Struct. 2003, 649, 287-307.
52. A. Streitwieser, Y.-J. Kim, J. Am. Chem. Soc. 2000, 122, 11783-11786.
53. C.-Y. Chen, Y.-S. Chang, S.-A. Lin, H.-I. Wen, Y.-C. Cheng, S.-W. Tsai, J. Org. Chem. 2002, 67, 3323-3326.
54. R. W. Taft, D. Gurka, L. Joris, P. von R. Schleyer, J. W. Rakshys, J. Am. Chem. Soc. 1969, 91, 4801-4808.
55. L. Joris, J. Mitsky, R. W. Taft, J. Am. Chem. Soc. 1972, 94, 3438-3442.
56. J. Graton, C. Laurence, M. Berthelot, J.-Y. Le Questel, F. Besseau, E. D. Raczyńska, J. Chem. Soc., Perkin Trans. 2 1999, 997-1001.
57. J. Graton, F. Besseau, M. Berthelot, E. D. Raczyńska, C. Laurence, Can. J. Chem. 2002, 80, 1375-1385.
58. M. Berthelot, C. Laurence, M. Safar, F. Besseau, J. Chem. Soc., Perkin Trans. 2 1998, 283-290.
59. M. Berthelot, C. Laurence, unpublished results.
60. P. A. Wade, N. V. Amin, H.-K. Yen, D. T. Price, G. F. Huhn, J. Org. Chem. 1984, 49, 4595-4601.
61. G. F. Field, W. J. Zally, Synthesis 1979, 295-296.
62. H. Minato, T. Nagasaki, T. Yokoshima, K. Suga, M. Yamaguchi, J. Labelled Compd. 1974, 10, 645-654.
63. King, G. S. P. D. Magnus, H. S. Rzepa, J. Chem. Soc., Perkin Trans. 1 1972, 437-443.
64. C. Bellandi, M. De Amici, C. De Micheli, Heterocycles 1984, 22, 2187-2190.
65. K. Hirota, Y. Kitade, S. Senda, J. Chem. Soc., Perkin Trans. 1 1984, 1859-1861.
66. H. Suguru, N. Hiroko, T. Yasuo, T. Keita, N. Nagatoshi, A. Masahiro, Heterocycles 1992, 34, 1511-1514.
67. N. Kornblum, W. M. Weaver, J. Am. Chem. Soc. 1958, 80, 4333-4337.
68. A. Baruah, B. Kalita, N. C. Barua, Synlett 2000, 1064-1066.
69. A. Shifman, M. Sprecher, S. Hoz, J. Phys. Org. Chem. 2000, 13, 105-111.
70. A. Corsaro, G. Perrini, V. Pistarà, P. Quadrelli, A. G. Invernizzi, P. Caramella, Tetrahedron 1996, 52, 6421-6436.
71. Y. S. Shabarov, L. G. Saginova, R. A. Gazzaeva, J. Org. Chem. USSR (Engl. Transl.), 1982, 18, 2319-2320;
72. Zh. Org. Khim. 1982, 18, 2627-2628.
73. F. A. Fouli, M. M. Habashy, A. F. El-Kafrawy, A. S. A. Youseef, M. M. El-Adly, J. Prakt. Chem. 1987, 329, 1116-1122.