Reaction of 5-hydroxyimino-1,3-dioxine-4,6-dione (isonitroso meldrum's acid) with carbodiimides to give parabanic acids

Heterocycles

Volumn 46, Issue 1, 1997, Pages 503-508

  Katagiri, Nobuya ^a   Morishita, Yoshihiro ^a   Kaneko, Chikara ^a  

^a TOHOKU UNIVERSITY   (Japan)

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Indexed keywords

EID: 0002620377     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/COM-97-S58     Document Type: Article

References (10)

1. N. Katagiri, A. Kurimoto, A. Yamada, H. Sato, T. Katsuhara, K. Takagi, and C. Kaneko, J. Chem. Soc., Chem. Commun., 1994, 281.
2. N. Katagiri, H. Sato, A. Kurimoto, M. Okada, A. Yamada, and C. Kaneko, J. Org. Chem., 1994, 59, 8101.
3. N. Katagiri, M. Okada, and C. Kaneko, Tetrahedron Lett., 1996, 37, 1801.
4. N. Katagiri, M. Okada, Y. Morishita, and C. Kaneko, J. Chem. Soc., Chem. Commun., 1996, 2137.
5. N. Katagiri, M. Okada, Y. Morishita, and C. Kaneko, Tetrahedron, 1997, 53, 5725.
6. Very recently, we have detected nitrosoketene (B) generated by pyrolysis of 1 using FTIR spectroscopy. H. Matsui, E. J. Zuckerman, N. Katagiri, C. Kaneko, S. Ham, and D. M. Birney, J. Phys. Chem. A, 1997, 101, 3936.
7. Compound (6) was also found to be formed in low yield (3.4 %) by heating of 1 in toluene. However, mechanism for the formation of 6 is obscure so far.
8. 1,3-Disubstituted parabanic acids are obtained from the reaction of oxalyl chloride with substituted ureas. a) P. J. Stoffel, J. Org. Chem., 1964, 29, 2794;
9. b) H. Ulrich and A. A. R. Sayigh, J. Org. Chem., 1965, 30, 2781.
10. H. Balli, R. Low, V. Muller, H. Rempfler, and A. Sezen-Gezgin, Helv. Chim. Acta, 1978, 61, 97.