DOI: 10.1039/A704354F
(Paper)
Reference Section for: J. Chem. Soc., Perkin Trans. 1, 1997, 2261-2262
Novel ring transformation of nitropyrimidinone; synthetic equivalent of α-nitroformylacetic acid
(Note: The full text of this document is currently only available in the PDF Version )
Nagatoshi Nishiwaki, Hui-Ping Wang, Kengo Matsuo, Yasuo Tohda and Masahiro Ariga
Abstract
3-Methyl-5-nitropyrimidin-4(3H)-one reacts with ketones in the presence of ammonium salts to afford disubstituted pyrimidines and disubstituted 3-nitro-2-pyridones in a novel ring transformation reaction; nitropyrimidinone behaves as an activated diformylamine in the former case, and as a synthetic equivalent of α-nitroformylacetic acid in the latter case.
References
- C. Kashima, H. Arao, S. Hibi and Y. Omote, Tetrahedron Lett., 1989, 30, 1561 CrossRef CAS; E. Allenstein and F. Sille, Chem. Ber., 1978, 111, 921 CAS; E. Allenstein and V. Beyl, Chem. Ber., 1967, 100, 3551 CrossRef CAS.
- W. Flitsch, K. Hampel and M. Hohenhorst, Liebigs Ann. Chem., 1990, 397 Search PubMed; W. Flitsch, K. Hampel and M. Hohenhorst, Tetrahedron Lett., 1987, 28, 4395 CrossRef CAS.
- N. Nishiwaki, T. Matsunaga, Y. Tohda and M. Ariga, Heterocycles, 1994, 39, 249.
- N. Nishiwaki, Y. Mizukawa, M. Ohta, R. Terai, Y. Tohda and M. Ariga, Heterocycl. Commun., 1996, 2, 21 Search PubMed.
- T. Meul, Patentschrift (Switz.), CH 682 562 A5/ 1993(Chem. Abstr., 1994, 120, 163 988) Search PubMed; V. Pomel, J. C. Rovera, A. Godard, F. Marsais and G. Quéguiner, J. Heterocycl. Chem., 1996, 33, 1995 Search PubMed.
- V. L. Rusinov, O. N. Chupakhin and H. C. van der Plas, Heterocycles, 1995, 40, 441 CAS and references cited therein.