cine-Substitution of 1-Methyl-3,6,8-trinitro-2-quinolone

Bulletin of the Chemical Society of Japan

Volumn 69, Issue 5, 1996, Pages 1377-1381

  Nishiwaki, Nagatoshi ^a   Tanaka, Aya ^a   Uchida, Mitsue ^a   Tohda, Yasuo ^a   Ariga, Masahiro ^a  

^a OSAKA KYOIKU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000298225     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.69.1377     Document Type: Article

References (22)

1. Pyridines: Y. Tohda, T. Kawahara, M. Eiraku, K. Tani, N. Nishiwaki, and M. Ariga, Bull. Chem. Soc. Jpn., 67, 2176 (1994); Phenols: E. Matsumura, M. Ariga, and Y. Tohda, Tetrahedron Lett., 1979, 1393; Anilines: E. Matsumura, Y. Tohda, and M. Ariga, Bull. Chem. Soc. Jpn., 55, 2174 (1982).
2. Pyridines: Y. Tohda, T. Kawahara, M. Eiraku, K. Tani, N. Nishiwaki, and M. Ariga, Bull. Chem. Soc. Jpn., 67, 2176 (1994); Phenols: E. Matsumura, M. Ariga, and Y. Tohda, Tetrahedron Lett., 1979, 1393; Anilines: E. Matsumura, Y. Tohda, and M. Ariga, Bull. Chem. Soc. Jpn., 55, 2174 (1982).
3. Pyridines: Y. Tohda, T. Kawahara, M. Eiraku, K. Tani, N. Nishiwaki, and M. Ariga, Bull. Chem. Soc. Jpn., 67, 2176 (1994); Phenols: E. Matsumura, M. Ariga, and Y. Tohda, Tetrahedron Lett., 1979, 1393; Anilines: E. Matsumura, Y. Tohda, and M. Ariga, Bull. Chem. Soc. Jpn., 55, 2174 (1982).
4. Ring transformation of [f] fused 2-pyridone (4H-quinolizin-4-one)was reported: M. Ariga and E. Matsumura, Bull. Chem. Soc. Jpn., 60, 1198 (1987).
5. M. Wozniak, A. Baranski, and K. Nowak, J. Org. Chem., 52, 5643 (1987).
6. All nucleophilic susceptibilities, dihedral angles, and heats of formation were estimated by MOPAC (PM3) molecular orbital calculation using CAChe system.
7. R. S. Varma, A. K. Chatterjee, and M. Varma, Tetrahedron Lett., 34, 3207 (1993).
8. C. Cativiela, J. L. Serrano, and M. M. Zurbano, J. Org. Chem., 60, 3074 (1995).
9. P. G. Gray, R. K. Norris, and T. A. Wright, J. Chem. Soc., Chem. Commun., 1979, 259.
10. G. Stork and C. A. Isaacs, J. Am. Chem. Soc., 112, 7399 (1990); F. Rose-Munch, E. Rose, and A. Semra, J. Chem. Soc., Chem. Commun., 1986, 1551.
11. G. Stork and C. A. Isaacs, J. Am. Chem. Soc., 112, 7399 (1990); F. Rose-Munch, E. Rose, and A. Semra, J. Chem. Soc., Chem. Commun., 1986, 1551.
12. 1, 2-Dinitrobenzene: D. P. Self, D. E. West, and M. R. Stillings, J. Chem. Soc., Chem. Commun., 1980, 281; 3-Dinitronaphthalene: G. Guanti, S. Thea, and C. Dell'Erba, Tetrahedron Lett., 1976, 461; 7-Dinitroquinoxaline: R. Nasielski-Hinkens, D. Pauwels, and J. Nasielski, Tetrahedron Lett., 1978, 2125; 4-Dinitropyrrole: G. Devincenzis, P. Mencarelli, and F. Stegel, J. Org. Chem., 48, 162 (1983); 4-Dinitrothiophene: M. Novi, G. Guanti, F. Sancassan, and C. D. Erba, J. Chem. Soc., Perkin Trans 1, 1978, 1140.
13. 1, 2-Dinitrobenzene: D. P. Self, D. E. West, and M. R. Stillings, J. Chem. Soc., Chem. Commun., 1980, 281; 3-Dinitronaphthalene: G. Guanti, S. Thea, and C. Dell'Erba, Tetrahedron Lett., 1976, 461; 7-Dinitroquinoxaline: R. Nasielski-Hinkens, D. Pauwels, and J. Nasielski, Tetrahedron Lett., 1978, 2125; 4-Dinitropyrrole: G. Devincenzis, P. Mencarelli, and F. Stegel, J. Org. Chem., 48, 162 (1983); 4-Dinitrothiophene: M. Novi, G. Guanti, F. Sancassan, and C. D. Erba, J. Chem. Soc., Perkin Trans 1, 1978, 1140.
14. 1, 2-Dinitrobenzene: D. P. Self, D. E. West, and M. R. Stillings, J. Chem. Soc., Chem. Commun., 1980, 281; 3-Dinitronaphthalene: G. Guanti, S. Thea, and C. Dell'Erba, Tetrahedron Lett., 1976, 461; 7-Dinitroquinoxaline: R. Nasielski-Hinkens, D. Pauwels, and J. Nasielski, Tetrahedron Lett., 1978, 2125; 4-Dinitropyrrole: G. Devincenzis, P. Mencarelli, and F. Stegel, J. Org. Chem., 48, 162 (1983); 4-Dinitrothiophene: M. Novi, G. Guanti, F. Sancassan, and C. D. Erba, J. Chem. Soc., Perkin Trans 1, 1978, 1140.
15. 1, 2-Dinitrobenzene: D. P. Self, D. E. West, and M. R. Stillings, J. Chem. Soc., Chem. Commun., 1980, 281; 3-Dinitronaphthalene: G. Guanti, S. Thea, and C. Dell'Erba, Tetrahedron Lett., 1976, 461; 7-Dinitroquinoxaline: R. Nasielski-Hinkens, D. Pauwels, and J. Nasielski, Tetrahedron Lett., 1978, 2125; 4-Dinitropyrrole: G. Devincenzis, P. Mencarelli, and F. Stegel, J. Org. Chem., 48, 162 (1983); 4-Dinitrothiophene: M. Novi, G. Guanti, F. Sancassan, and C. D. Erba, J. Chem. Soc., Perkin Trans 1, 1978, 1140.
16. 1, 2-Dinitrobenzene: D. P. Self, D. E. West, and M. R. Stillings, J. Chem. Soc., Chem. Commun., 1980, 281; 3-Dinitronaphthalene: G. Guanti, S. Thea, and C. Dell'Erba, Tetrahedron Lett., 1976, 461; 7-Dinitroquinoxaline: R. Nasielski-Hinkens, D. Pauwels, and J. Nasielski, Tetrahedron Lett., 1978, 2125; 4-Dinitropyrrole: G. Devincenzis, P. Mencarelli, and F. Stegel, J. Org. Chem., 48, 162 (1983); 4-Dinitrothiophene: M. Novi, G. Guanti, F. Sancassan, and C. D. Erba, J. Chem. Soc., Perkin Trans 1, 1978, 1140.
17. S. A. Barr and D. R. Boyd, J. Chem. Soc., Chem. Commun., 1994, 153; G. Brader, G. Wurz, H. Greger, and O. Hofer, Liebigs Ann. Chem., 1993, 355; P. Kumar, B. P. Das, and S. K. P. Sinha, Chem. Ind., 1986, 669; P. Bhattacharyya and B. K. Chowdhury, Phytochemistry, 24, 634 (1985).
18. S. A. Barr and D. R. Boyd, J. Chem. Soc., Chem. Commun., 1994, 153; G. Brader, G. Wurz, H. Greger, and O. Hofer, Liebigs Ann. Chem., 1993, 355; P. Kumar, B. P. Das, and S. K. P. Sinha, Chem. Ind., 1986, 669; P. Bhattacharyya and B. K. Chowdhury, Phytochemistry, 24, 634 (1985).
19. S. A. Barr and D. R. Boyd, J. Chem. Soc., Chem. Commun., 1994, 153; G. Brader, G. Wurz, H. Greger, and O. Hofer, Liebigs Ann. Chem., 1993, 355; P. Kumar, B. P. Das, and S. K. P. Sinha, Chem. Ind., 1986, 669; P. Bhattacharyya and B. K. Chowdhury, Phytochemistry, 24, 634 (1985).
20. S. A. Barr and D. R. Boyd, J. Chem. Soc., Chem. Commun., 1994, 153; G. Brader, G. Wurz, H. Greger, and O. Hofer, Liebigs Ann. Chem., 1993, 355; P. Kumar, B. P. Das, and S. K. P. Sinha, Chem. Ind., 1986, 669; P. Bhattacharyya and B. K. Chowdhury, Phytochemistry, 24, 634 (1985).
21. E. A. Prill and S. M. McElvain, Org. Synth., Coll. Vol. 2, 419 (1943).
22. "Beilstein Handbook of Organic Chemistry," Basic Series, Vol. 21, p. 310.