Syntheses of polyfunctionalized compounds using nitroisoxazolones

Yuki Gosei Kagaku Kyokaishi/Journal of Synthetic Organic Chemistry

Volumn 63, Issue 12, 2005, Pages 1232-1238

  Nishiwaki, Nagatoshi ^a   Tamura, Mina ^a   Ariga, Masahiro ^a  

^a OSAKA KYOIKU UNIVERSITY   (Japan)

Author keywords

Amidoxime; Cyano aci nitroacetate; Isoxazole; Nitrile oxide; Nitroenamine; Nitroisoxazolone; Nitroketene aminal; Pyrrole; Ring opening reaction; Ring transformation

Indexed keywords

ALDEHYDES; AMINES; CONDENSATION; DERIVATIVES; KETONES; SALTS; SYNTHESIS (CHEMICAL);

AMIDOXIME; CYANO-ACI-NITROACETATE; ISOXAZOLE; NITRILE OXIDE; NITROENAMINE; NITROISOXAZOLONE; NITROKETENE AMINAL; PYRROLE; RING OPENING REACTION; RING TRANSFORMATION;

NITROGEN COMPOUNDS;

EID: 33244459362     PISSN: 00379980     EISSN: None     Source Type: Journal    
DOI: 10.5059/yukigoseikyokaishi.63.1232     Document Type: Article

References (37)

1. S. A. Lang Jr., Y.-i. Lin, "Isoxazoles and their Benzo Derivatives in Comprehensive Heterocyclic Chemistry", Vol. 6, ed. by K. T. Potts, Pergamon Press, Oxford, 1984, pp 1-130
2. R. H. Prager, C. M. Williams, Heterocycles, 51, 3013 (1999)
3. R. Nesi, S. Chimichi, F. D. Sio, R. Pepino, P. Tedeschi, Tetrahedron Lett., 23, 4397 (1982)
4. M. Ariga, Y. Tohda, H. Nakashima, K. Tani, Y. Mori, E. Ma tsumura, Bull. Chem. Soc. Jpn., 64, 3544 (1991)
5. M. J. Kamlet, J. Org. Chem., 24, 714 (1959)
6. N. Nishiwaki, Y. Takada, K. Tani, Y. Tohda, M. Ariga, Chem. Express, 7, 845 (1992)
7. N. Nishiwaki, Y. Takada, Y. Inoue, Y. Tohda, M. Ariga, J. Heterocycl. Chem., 32, 473 (1995)
8. (a) L. D. Quin, D. O. Pinion, J. Org. Chem., 35, 3130 (1970);
9. (b) F. De Sarlo, G. Dini, J. Hetrocycl. Chem., 4, 533 (1967)
10. C. Ulpiani, Gazz. Chim. Ital., 42, 209 (1912)
11. N. Nishiwaki, T. Nogami, C. Tanaka, F. Nakashima, Y. Inoue, N. Asaka, Y. Tohda, M. Ariga, J. Org. Chem., 64, 2160 (1999)
12. T. Mechkov, Z. Demireva, Z. Chem., 29, 291 (1989)
13. N. Nishiwaki, T. Nogami, T. Kawamura, F. Nakashima, N. Asaka, Y. Tohda, M. Ariga, J. Org. Chem., 64, 6476 (1999)
14. K. G. B. Torsell, "Nitrite Oxides, Nitrones, and Nitronates in Organic Synthesis", VCH, Weinheim, 1988, pp 95-127
15. (a) S. P. Gromov, Heterocycles, 53, 1607 (2000);
16. (b) H. C. van der Plas, J. Hetrocycl. Chem., 37, 427 (2000);
17. H. C. van der Plas, "Adv. Heterocycl. Chem.", Vol. 74, ed. by A. R. Katritzky, Academic Press, London, 1999;
18. V. L. Rusinov, O. N. Chupakhin, H. C. van der Plas, Heterocycles, 40, 441 (1995);
19. (e) E. V. Babaev, S. I. Bobrovskii, Y. G. Bundel, Khim. Geterotsikl. Soedin., 1988, 1570
20. M. Tamura, T. Nishimura, N. Nishiwaki, M. Ariga, Heterocycles, 63, 1659 (2004)
21. R. J. Gout, "Biological Reactions and Pharmaceutical Uses of Imidic Acid Derivatives, in The Chemistry of the Amidines and Imidates" ed. by S. Patai, John Wiley & Sons, London, 1975, pp 255-282
22. N. Nishiwaki, Y. Okajima, M. Tamura, N. Asaka, K. Hori, Y. Tohda, M. Ariga, Heterocycles, 60, 303 (2003)
23. (a) S. Rajappa, Tetrahedron, 55, 7065 (1999);
24. (b) V. V. Perekalin, E. S. Lipina, V. M. Berestovitskaya, D. A. Efremov, "Nitroalkenes, Conjugated Nitro Compounds", John Wiley and Sons, Inc., New York, 1994, pp 210-231;
25. S. Rajappa, Tetrahedron, 37, 1453 (1981)
26. S. Higashida, H. Nakashima, Y. Tohda, K. Tani, N. Nishiwaki, M. Ariga, Heterocycles, 34, 1511 (1992)
27. N. Nishiwaki, T. Uehara, N. Asaka, Y. Tohda, M. Ariga, S. Kanemasa, Tetrahedron Lett., 39, 4851 (1998)
28. (a) A. K. Parhi, R. W. Franck, Org. Lett., 6, 3063 (2004);
29. (b) M. G. Leslie-Smith, R. M. Paton, N. Webb, Tetrahedron Lett., 35, 9251 (1994);
30. R. Huisgen, M. Christi, Chem. Ber., 106, 3291 (1973);
31. R. Paul, S. Tchelitcheff, Bull. Soc. Chim. Fr., 1963, 140
32. (a) N. Nishiwaki, M. Nakanishi, T. Hida, Y. Miwa, M. Tamura, K. Hori, Y. Tohda, M. Ariga, J. Org. Chem., 66, 7535 (2001);
33. (b) M. Ariga, N. Nishiwaki, Y. Miwa, K. Tani, Y. Tohda, Heterocyclces, 44, 81 (1997)
34. (a) N. G. Anthony, B. F. Johnston, A. I. Khalaf, S. M. MacKay, J. A. Parkinson, C. J. Suckling, R. D. Waigh, J. Am. Chem. Soc., 126, 11338 (2004);
35. (b) T. Bando, A. Narita, K. Asada, H. Ayame, H. Sugiyama,J. Am. Chem. Soc. ibid., 126, 8948 (2004);
36. A. L. Satz, T. C. Bruice, Acc. Chem. Res., 35, 86 (2002)
37. J. H. Boyer, "Nitroazoles", VCH, New York, 1986, pp 40-47