2-methyl-4-nitroisoxazolin-5-one: Ring transformation to 3-nitropyrroles

Heterocycles

Volumn 44, Issue 1, 1997, Pages 81-84

  Ariga, Masahiro ^a   Nishiwaki, Nagatoshi ^a   Miwa, Yuko ^a   Tani, Keita ^a   Tohda, Yasuo ^a  

^a OSAKA KYOIKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0003422753     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-96-S15     Document Type: Article

References (16)

1. M. Ariga, Y. Tohda, H. Nakashima, K. Tani, Y. Mon, and E. Matsumura, Bull. Chem. Soc. Jpn., 1991, 64, 3544.
2. S. Higashida, H, Nakashima, Y. Tohda, K. Tani, N. Nishiwaki, and M. Ariga, Heterocycles, 1992, 34, 1511.
3. N. Nishiwaki, Y. Takada, Y. Tohda, and M. Ariga, Chem. Express, 1992, 7, 845.
4. 3): δ 1.42 (t, J=7 Hz, 3H), 2.64 (s, 3H), 3.94 (s, 3H), 4.36 (q, J=7 Hz, 2H), 7.60 (s, 1H).
5. 3): δ 1.37 (t, J=7 Hz, 3H), 1.38 (t, J=7 Hz, 3H), 2.51 (s, 3H), 2.55 (s, 3H), 3.78 (s, 3H), 4.28 (q, J=7 Hz, 2H), 4.30 (q, J=7 Hz, 2H).
6. W. G. Terry, A. H. Jackson, G. W. Kenner, and G. Kornis, J. Chem. Soc., 1965, 4389.
7. 3): δ 1.27 (t, J=7 Hz, 3H), 1.37 (t, J=7 Hz, 3H), 3.96 (s, 3H), 4.18 (q, J=7 Hz, 2H), 4.28 (s, 2H), 4.34 (q, J=7 Hz, 2H), 7.64 (s, 1H).
8. 3): δ 2.52 (s, 3H), 2.69 (s, 3H), 3.90 (s, 3H), 7.63 (s, 1H).
9. 3): E-5 c: δ 2.10 (s, 6H), 3.29 (s, 3H), 6.46 (d, J=11 Hz, 1H), 8.16 (d, J=11 Hz, 1H), 15.71 (s, 1H); Z-5 c: δ 2.10 (s, 6H), 3.03 (s, 3H), 6.72 (d, J=11 Hz, 1H), 7.92 (d, J=11 Hz, 1H), 15.53 (s,1H).
10. N. Nishiwaki, E. Wakamura, Y. Nishida, Y. Tohda, and M. Ariga, Heterocyclic Commun., 1996, 2, in press.
11. S. Rajappa and K. Nagarajan, J. Chem. Soc., Perkin Trans. II, 1978, 912.
12. F. de Sarlo and G. Renzi, Tetrahedron, 1966, 22, 2995.
13. D. J. Woodman, C. H. Borman, N. Tontapanish, and P. M. Stonebraker, J. Org. Chem., 1969, 34, 2981.
14. H. J. Wollweber and C. Wentrup, J. Org. Chem., 1985, 50, 2041.
15. N. Nishiwaki, Y. Takada, Y. Inoue, Y. Tohda, and M. Ariga, J. Heterocycl. Chem., 1995, 32, 473.
16. H. C. van der Plas, "Ring Transformations of Heterocycles", Vol. 1, Chapt. 3, Academic Press, New York, 1973.