A New Synthesis of 4-Phosphorylchromenes from 3-Nitrochromenes

Journal of Heterocyclic Chemistry

Volumn 34, Issue 4, 1997, Pages 1243-1246

  Ono, Noboru ^a   Banshou, Natsuko ^a   Ito, Satoshi ^a   Murashima, Takashi ^a   Ogawa, Takuji ^a  

^a EHIME UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 1542465787     PISSN: 0022152X     EISSN: None     Source Type: Journal    
DOI: 10.1002/jhet.5570340424     Document Type: Article

References (25)

1. E. E. Schweizer and D. Meeder-Nycz, in Chromenes, Chromanones, and Chromones, G. P. Ellis, ed, The Chemistry of Heterocyclic Compounds, John Wiley and Sons, New York, 1977, p 29.
2. V. A. Ashwood, R. E. Buckingham, F. Cassidy, J. M. Evans, E. A. Faruk, T. C. Hamilton, D. J. Nash, G. Stemp, and K. Willcocks, J. Med. Chem., 29, 2194 (1986).
3. H. Koga, H. Sato, T. Ishizawa, N. Taka, and T. Takahashi, Tetrahedron Letters, 36, 87 (1995).
4. [4a] D. R. Buckle, D. S. Eggleston, I. L. Pinto, D. G. Smith, and J. M. Tedder, Biomed. Chem. Letters, 2, 1161 (1992);
5. [b] R. Bergmann and R. Gericke, J. Med. Chem., 33, 492 (1990).
6. D. M. Robertson and M. I. Steinberg, J. Med. Chem., 33, 1529 (1990).
7. N. Ono, K. Sugi, T. Ogawa, and S. Aramaki, J. Chem. Soc. Chem. Commun., 1781 (1993).
8. [7a] R. Engel, Chem. Rev., 77, 349 (1977);
9. [b] M. R. Harnden, A. Parkin, M. J. Parratt, and R. M. Perkins, J. Med. Chem., 36, 1345 (1993).
10. For recent review, see, T. Minami and J. Motoyoshiya, Synthesis, 333 (1992).
11. The nitro and cyano groups have been mostly used as an electron acceptor for non-linear optical devices, see; [a] P. N. Prasad and D. J. Williams, Introduction to Nonlinear Optical Effective Molecules and Properties, John Wiley and Sons, New York, 1991. The functional groups consisted of the third row elements such as sulfonyl or phosphonyl groups may be better for the colorless materials than the nitro or cyano group, see: [b] S. Nijhuis, G. L. Rikken, E. E. Havinga, W. T. Hoeve, H. Wynberg, E. W. Meijer, J. Chem. Soc., Chem. Commun., 1093 (1990); [c] C. Dehu, F. Meyers, J. L. Bredas, J. Am. Chem. Soc., 115, 6198 (1993); [d] The second harmonic generation efficiency of β-phosphonyl p-dimethylaminostyrene is 13 times that of urea, whose efficiency is better than the corresponding nitro compounds; see T. Ogawa, N, Usuki, and N. Ono, Abstract of the 68th National Meeting of the Chemical Society of Japan, Nagoya, 1A406 (1994).
12. The nitro and cyano groups have been mostly used as an electron acceptor for non-linear optical devices, see; [a] P. N. Prasad and D. J. Williams, Introduction to Nonlinear Optical Effective Molecules and Properties, John Wiley and Sons, New York, 1991. The functional groups consisted of the third row elements such as sulfonyl or phosphonyl groups may be better for the colorless materials than the nitro or cyano group, see: [b] S. Nijhuis, G. L. Rikken, E. E. Havinga, W. T. Hoeve, H. Wynberg, E. W. Meijer, J. Chem. Soc., Chem. Commun., 1093 (1990); [c] C. Dehu, F. Meyers, J. L. Bredas, J. Am. Chem. Soc., 115, 6198 (1993); [d] The second harmonic generation efficiency of β-phosphonyl p-dimethylaminostyrene is 13 times that of urea, whose efficiency is better than the corresponding nitro compounds; see T. Ogawa, N, Usuki, and N. Ono, Abstract of the 68th National Meeting of the Chemical Society of Japan, Nagoya, 1A406 (1994).
13. The nitro and cyano groups have been mostly used as an electron acceptor for non-linear optical devices, see; [a] P. N. Prasad and D. J. Williams, Introduction to Nonlinear Optical Effective Molecules and Properties, John Wiley and Sons, New York, 1991. The functional groups consisted of the third row elements such as sulfonyl or phosphonyl groups may be better for the colorless materials than the nitro or cyano group, see: [b] S. Nijhuis, G. L. Rikken, E. E. Havinga, W. T. Hoeve, H. Wynberg, E. W. Meijer, J. Chem. Soc., Chem. Commun., 1093 (1990); [c] C. Dehu, F. Meyers, J. L. Bredas, J. Am. Chem. Soc., 115, 6198 (1993); [d] The second harmonic generation efficiency of β-phosphonyl p-dimethylaminostyrene is 13 times that of urea, whose efficiency is better than the corresponding nitro compounds; see T. Ogawa, N, Usuki, and N. Ono, Abstract of the 68th National Meeting of the Chemical Society of Japan, Nagoya, 1A406 (1994).
14. The nitro and cyano groups have been mostly used as an electron acceptor for non-linear optical devices, see; [a] P. N. Prasad and D. J. Williams, Introduction to Nonlinear Optical Effective Molecules and Properties, John Wiley and Sons, New York, 1991. The functional groups consisted of the third row elements such as sulfonyl or phosphonyl groups may be better for the colorless materials than the nitro or cyano group, see: [b] S. Nijhuis, G. L. Rikken, E. E. Havinga, W. T. Hoeve, H. Wynberg, E. W. Meijer, J. Chem. Soc., Chem. Commun., 1093 (1990); [c] C. Dehu, F. Meyers, J. L. Bredas, J. Am. Chem. Soc., 115, 6198 (1993); [d] The second harmonic generation efficiency of β-phosphonyl p-dimethylaminostyrene is 13 times that of urea, whose efficiency is better than the corresponding nitro compounds; see T. Ogawa, N, Usuki, and N. Ono, Abstract of the 68th National Meeting of the Chemical Society of Japan, Nagoya, 1A406 (1994).
15. S. V. Rajender, K. Mirayam, and W. K. Geroge, Synthesis, 486 (1982).
16. E. Hata, T. Yamada, and T. Mukaiyama, Bull. Chem. Soc. Japan, 68, 3629 (1995).
17. Y. Xu, M. T. Flavin, and Ze-Qi Xu, J. Org. Chem., 61, 7697 (1996) and references therein.
18. A. Bhattacharya and G. Thyagarajan, Chem. Rev., 81, 415 (1981).
19. Li-Ban Han and M. Tanaka, J. Am. Chem. Soc., 118, 1571 (1996).
20. [15a] For a review on this topic, see: N. Ono, in Nitro Compounds: Recent Advances in Synthesis and Chemistry, H. Feuer and T. N. Nielsen, eds, VCH Publishers; New York, 1990;
21. Chapter 1, for recent papers, see: [b] C. D. Weis and G. R. Newkome, J. Org. Chem., 55, 5801 (1990); [c] R. Ballini, and G. Bosica, Tetrahedron, 51, 4213 (1995); [d] R. Ballini and P. Astolfi, Liebigs Ann., 1879 (1996).
22. Chapter 1, for recent papers, see: [b] C. D. Weis and G. R. Newkome, J. Org. Chem., 55, 5801 (1990); [c] R. Ballini, and G. Bosica, Tetrahedron, 51, 4213 (1995); [d] R. Ballini and P. Astolfi, Liebigs Ann., 1879 (1996).
23. Chapter 1, for recent papers, see: [b] C. D. Weis and G. R. Newkome, J. Org. Chem., 55, 5801 (1990); [c] R. Ballini, and G. Bosica, Tetrahedron, 51, 4213 (1995); [d] R. Ballini and P. Astolfi, Liebigs Ann., 1879 (1996).
24. M. Yamada and M. Yamashita, Synthesis, 1026 (1982).
25. H. A. Kurtz, J. J. P. Stewart, and K, M, Dieter, J. Comput. Chem., 11, 82 (1990).