New Synthesis of Fused Pyrimidine Derivatives via ortho-(Isocyanomethyl)nitroaromatic Compounds

Journal of Chemical Research - Part S

Volumn , Issue 1, 1998, Pages 14-15

  Ostrowski, Stanisław ^a  

^a INSTITUTE OF ORGANIC CHEMISTRY   (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 2542513877     PISSN: 03082342     EISSN: None     Source Type: Journal    
DOI: 10.1039/a703092d     Document Type: Article

References (36)

1. D. J. Brown, in The Chemistry of Heterocyclic Compounds, The Pyrimidines, ed. E. C. Taylor, Wiley, New York, 1994.
2. (a) W. L. F. Armarego, in The Chemistry of Heterocyclic Compounds, Fused Pyrimidines, Part I: Quinazolines, ed. D. J. Brown, Interscience, New York, 1967;
3. (b) J. H. Lister, ibid., Part II: Purines, ed. D. J. Brown, Wiley-Interscience, New York, 1971;
4. (c) D. J. Brown, ibid., Part III: Pteridines, ed. E. C. Taylor, Wiley, New York, 1988;
5. (d) T. J. Delia, ibid., Part IV: Miscellaneous Fused Pyrimidines, ed. E. C. Taylor, Wiley, New York, 1992.
6. Bischler's synthesis: A. Bischler, Ber. Dtsch. Chem. Ges., 1891, 24, 506; W. L. F. Armarego and J. I. Smith, J. Chem. Soc. C, 1966, 234; Riedel's synthesis: A. Riedel, Ger. Pat. 174941, 1905; M. T. Bogert and E. M. McColm, J. Am. Chem. Soc., 1927, 49, 2650; W. L. F. Armarego, J. Chem. Soc., 1962, 561; Niementowski's synthesis: S. Niementowski, J. Prakt. Chem., 1895, 51(2), 564; ref. 2(a), pp. 74-78.
7. Bischler's synthesis: A. Bischler, Ber. Dtsch. Chem. Ges., 1891, 24, 506; W. L. F. Armarego and J. I. Smith, J. Chem. Soc. C, 1966, 234; Riedel's synthesis: A. Riedel, Ger. Pat. 174941, 1905; M. T. Bogert and E. M. McColm, J. Am. Chem. Soc., 1927, 49, 2650; W. L. F. Armarego, J. Chem. Soc., 1962, 561; Niementowski's synthesis: S. Niementowski, J. Prakt. Chem., 1895, 51(2), 564; ref. 2(a), pp. 74-78.
8. Bischler's synthesis: A. Bischler, Ber. Dtsch. Chem. Ges., 1891, 24, 506; W. L. F. Armarego and J. I. Smith, J. Chem. Soc. C, 1966, 234; Riedel's synthesis: A. Riedel, Ger. Pat. 174941, 1905; M. T. Bogert and E. M. McColm, J. Am. Chem. Soc., 1927, 49, 2650; W. L. F. Armarego, J. Chem. Soc., 1962, 561; Niementowski's synthesis: S. Niementowski, J. Prakt. Chem., 1895, 51(2), 564; ref. 2(a), pp. 74-78.
9. Bischler's synthesis: A. Bischler, Ber. Dtsch. Chem. Ges., 1891, 24, 506; W. L. F. Armarego and J. I. Smith, J. Chem. Soc. C, 1966, 234; Riedel's synthesis: A. Riedel, Ger. Pat. 174941, 1905; M. T. Bogert and E. M. McColm, J. Am. Chem. Soc., 1927, 49, 2650; W. L. F. Armarego, J. Chem. Soc., 1962, 561; Niementowski's synthesis: S. Niementowski, J. Prakt. Chem., 1895, 51(2), 564; ref. 2(a), pp. 74-78.
10. Bischler's synthesis: A. Bischler, Ber. Dtsch. Chem. Ges., 1891, 24, 506; W. L. F. Armarego and J. I. Smith, J. Chem. Soc. C, 1966, 234; Riedel's synthesis: A. Riedel, Ger. Pat. 174941, 1905; M. T. Bogert and E. M. McColm, J. Am. Chem. Soc., 1927, 49, 2650; W. L. F. Armarego, J. Chem. Soc., 1962, 561; Niementowski's synthesis: S. Niementowski, J. Prakt. Chem., 1895, 51(2), 564; ref. 2(a), pp. 74-78.
11. Bischler's synthesis: A. Bischler, Ber. Dtsch. Chem. Ges., 1891, 24, 506; W. L. F. Armarego and J. I. Smith, J. Chem. Soc. C, 1966, 234; Riedel's synthesis: A. Riedel, Ger. Pat. 174941, 1905; M. T. Bogert and E. M. McColm, J. Am. Chem. Soc., 1927, 49, 2650; W. L. F. Armarego, J. Chem. Soc., 1962, 561; Niementowski's synthesis: S. Niementowski, J. Prakt. Chem., 1895, 51(2), 564; ref. 2(a), pp. 74-78.
12. Bischler's synthesis: A. Bischler, Ber. Dtsch. Chem. Ges., 1891, 24, 506; W. L. F. Armarego and J. I. Smith, J. Chem. Soc. C, 1966, 234; Riedel's synthesis: A. Riedel, Ger. Pat. 174941, 1905; M. T. Bogert and E. M. McColm, J. Am. Chem. Soc., 1927, 49, 2650; W. L. F. Armarego, J. Chem. Soc., 1962, 561; Niementowski's synthesis: S. Niementowski, J. Prakt. Chem., 1895, 51(2), 564; ref. 2(a), pp. 74-78.
13. (a) D. Chakravarti, R. N. Chakravarti, L. A. Cohen, B. Dasgupta, S. Datta and H. K. Miller, Tetrahedron, 1961, 16, 224;
14. (b) S. C. Pakrashi, J. Bhattacharyya, L. F. Johnson and H. Budzikiewicz, Tetrahedron, 1963, 19, 1011;
15. (c) G. C. Muñoz and R. Madroñero, Chem. Ber., 1962, 95, 2182.
16. (a) B. R. Baker, R. E. Schaub, J. P. Joseph, F. J. McEvoy and J. H. Williams, J. Org. Chem., 1952, 17, 164;
17. (b) N. J. Leonard and M. J. Martell Jr., Tetrahedron Lett., 1960, 25, 44;
18. (c) S. C. Bell and S. J. Childress, J. Org. Chem., 1962, 27, 1691;
19. (d) T. Goto, Y. Kishi, S. Takahashi and Y. Hirata, Tetrahedron, 1965, 21, 2059.
20. (a) H. E. Zaugg and W. B. Martin, Org. React., 1965, 14, 52;
21. (b) S. Kano, Y. Tanaka, S. Sugino and S. Hibino, Synthesis, 1980, 695:
22. (c) Y. Tomioka, K. Ohkubo and M. Yamazaki, Chem. Pharm. Bull., 1985, 33, 1360.
23. M. Makosza, A. J. Kinowski and S. Ostrowski, Synthesis, 1993, 1215.
24. K. Schofield and T. Swain, J. Chem. Soc., 1949, 1367.
25. T. Koyama, T. Hirota, F. Yagi, S. Ohmori and M. Yamata, Chem. Pharm. Bull., 1975, 23, 3151.
26. A. Bendich, P. J. Russell Jr. and J. J. Fox, J. Am. Chem. Soc., 1954, 76, 6073.
27. (a) J. Sarasin and E. Wegmann, Helv. Chim. Acta, 1924, 7, 713;
28. (b) A. H. Cook and E. Smith, J. Chem. Soc., 1949, 2329, 3001;
29. (c) G. Shaw and D. N. Butler, J. Chem. Soc., 1959, 4040;
30. (d) R. N. Naylor, G. Shaw, D. V. Wilson and D. N. Butler, J. Chem. Soc., 3961, 4845;
31. (e) K. Kadir, G. Shaw and D. Wright, J. Chem. Soc., Perkin Trans. 1, 1980, 2728;
32. (f) K. E. Andersen and E. B. Pedersen, Liebigs Ann. Chem., 1985, 921;
33. (g) P. R. Birkett, H. King, Ch. B. Chapleo, D. F. Ewing and D. Mackenzie, Tetrahedron, 1993, 49, 11029.
34. (a) S. Ostrowski, Synlett, 1995, 253;
35. (b) S Ostrowski, Heterocycles, 1996, 43, 389.
36. S. Ostrowski, in preparation.