Two ring transformations of 3-methyl-5-nitropyrimidin-4(3H)-one for the construction of azaheterocycles

Journal of the Chemical Society, Perkin Transactions 1

Volumn , Issue 1, 2000, Pages 27-31

  Nishiwaki, Nagatoshi ^a   Adachi, Tomoko ^a   Matsuo, Kengo ^a   Wang, Hui Ping ^a   Matsunaga, Tomoko ^a   Tohda, Yasuo ^a   Ariga, Masahiro ^a  

^a OSAKA KYOIKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMMONIUM COMPOUNDS; CHROMATOGRAPHIC ANALYSIS; ELECTRONS; METHANOL; SYNTHESIS (CHEMICAL);

RING TRANSFORMATIONS;

ORGANIC COMPOUNDS;

EID: 0034614729     PISSN: 14704358     EISSN: None     Source Type: Journal    
DOI: 10.1039/a907728f     Document Type: Article

References (31)

1. H. C. van der Plas, Ring Transformations of Heterocycles, Vol. 1-2, Academic Press, London, 1973.
2. V. L. Rusinov, O. N. Chupakhin and H. C. van der Plas, Heterocycles, 1995, 40, 441 and references cited therein.
3. 2(1H)-one: J. J. Fox, T.-L. Su, L. M. Stempel and K. A. Watanabe, J. Org. Chem.,1982, 47, 1081.
4. 4(1H)-one: N. Nishiwaki, E. Wakamura, Y. Nishida, Y. Tohda and M. Ariga, Heterocycl. Commun., 1996, 2, 129.
5. 2(1W)-one: N. Nishiwaki, Y. Tohda and M. Ariga, Bull. Chem. Soc. Jpn., 1996, 69, 1997.
6. 2(1H)-one and 4(3H)-one: N. Nishiwaki, Y. Tohda and M. Ariga, Synthesis, 1997, 1277.
7. 4(3H)-one: N. Nishiwaki, Y. Mizukawa, M. Ohta, R. Terai, Y. Tohda and M. Ariga, Heterocycl. Commun., 1996, 2, 21.
8. 4(3H)-one: N. Nishiwaki, T. Matsunaga, Y. Tohda and M. Ariga, Heterocycles, 1994, 38, 249.
9. 4(3H)-one: N. Nishiwaki, H.-P. Wang, K. Matsuo, Y. Tohda and M. Ariga, J. Chem. Soc., Perkin Trans. 1, 1997, 2261.
10. Y. Tohda, M. Eiraku, T. Nakagawa, Y. Usami, M. Ariga, T. Kawashima, K. Tani, H. Watanabe and Y. Mori, Bull. Chem. Soc. Jpn., 1990, 63, 2820.
11. (a) 5a-c: D. L. Boger, J. Schumacher, M. D. Mullican, M. Patel and J. S. Panek, J. Org. Chem., 1982, 47, 2673;
12. (b) 5a, 5c: E. Breitmaier, Angew: Chem., 1971, 83, 287;
13. (c) 5b: T. Koyama, T. Hirota, C. Basho, Y. Watanabe, Y. Kitauchi, Y. Satoh, S. Ohmaori and M. Yamato, Chem. Pharm. Bull., 1976, 24, 1459;
14. (d) 5b: L. O. Ross, L. Goodman and B. R. Baker, J. Am. Chem. Soc., 1959, 81, 3108;
15. (e) 5d: E. T. Olejniczak, P. J. Hajduk, P. A. Marcotte, D. G. Nettesheim, R. P. Meadows, R. Edalji, T. F. Holzman and S. W. Fesik, J. Am. Chem. Soc., 1997, 119, 5828;
16. (f) 5d, 5g: D. J. Brown and B. T. England, J. Chem. Soc. C, 1971, 425;
17. (g) 5d-e: H. Bredereck, R. Gompper and H. Herlinger, Chem. Ber., 1958, 91, 2832.
18. D. J. Brown, Comprehensive Heterocyclic Chemistry, ed. A. J. Boulton and A. McKillop, Pergamon Press, Oxford, 1984, vol. 3, pp. 57-155.
19. D. J. Brown, The Chemistry of Heterocyclic Compounds, ed. E. C. Taylor, John Wiley & Sons, New York, 1993, vol. 52, pp. 89-93.
20. N. P. Shusherina and T. I. Likhomanova, Chem. Heterocycl. Compd. (Engl. Transl.), 1974, 1242
21. (Translated from Khim Geterotsikl. Soedin., 1972, 1374).
22. (a) V. Pomel, J. C. Rovera, A. Godard, F. Marsais and G. Quéguiner, J. Heterocycl. Chem., 1996, 33, 1995;
23. (b) J. S. Wai, T. M. Williams, D. L. Bamberger, T. E. Fisher, J. M. Hoffman, R. J. Hudcosky, S. C. MacTough, C. S. Rooney, W. S. Saari, C. M. Thomas, M. E. Goldman, J. A. O'Brien, E. A. Emini, J. H. Nunberg, J. C. Quintero, W. A. Schleif and P. S. Andersen, J. Med. Chem., 1993, 36, 249;
24. (c) P. Rocca, F. Marsais, A. Godard and G. Quéguiner, Tetrahedron Lett., 1993, 34, 2837;
25. (d) J. M. Hoffman, J. S. Wai, C. M. Thomas, R. B. Levin, J. A. O'Brien and M. E. Goldman, J. Med. Chem., 1992, 35, 3784;
26. (e) T. B. Perrior, Eur. Pat. Appl, 0367410 A1/1990: (Chem. Abstr., 1990, 113, 171890);
27. (f) T.-Y. Shen, R. L. Clark, A. A. Pessolano, B. E. Witzel and T. J. Lanza, US Pat., 4038396/1977 (Chem. Abstr., 1977, 87, 152185).
28. (a) T. Ueda, S. Asai, K. Oiji, S.-I. Nagai, A. Nagatsu and J. Sakakibara, J. Heterocycl. Chem., 1997, 34, 761;
29. (b) I. Matsuura, T. Ueda, N. Murakami, S.-I. Nagai, A. Nagatsu and J. Sakakibara, J. Chem. Soc., Perkin Trans, 1, 1993, 965.
30. The estimation of nucleophilic susceptibility was conducted by a MOPAC (PM3) molecular orbital calculation using the CAChe system.
31. L. Bauer, G. E. Wright, B. A. Mikrut and C. L. Bell, J. Heterocycl. Chem., 1965, 2, 447.