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

Abstract

An efficient synthesis of functionalized fused pyrimidine derivatives from the respective ortho-(isocyanomethyl)nitroarenes is described: hydrolysis of the isocyano group in the title isocyanides followed by catalytic reduction of the nitro group and subsequent cyclocondensation of the diamine formed with orthoesters leads to the final products.

References

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; (b) J. H. Lister, ibid., Part II: Purines, ed. D. J. Brown, Wiley–Interscience, New York, 1971; (c) D. J. Brown, ibid., Part III: Pteridines, ed. E. C. Taylor, Wiley, New York, 1988; (d) T. J. Delia, ibid., Part IV: Miscellaneous Fused Pyrimidines, ed. E. C. Taylor, Wiley, New York, 1992.
3. 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.
4. (a) D. Chakravarti, R. N. Chakravarti, L. A. Cohen, B. Dasgupta, S. Datta and H. K. Miller, Tetrahedron, 1961, 16, 224; (b) S. C. Pakrashi, J. Bhattacharyya, L. F. Johnson and H. Budzikiewicz, Tetrahedron, 1963, 19, 1011; (c) G. C. Muñoz and R. Madroñero, Chem. Ber., 1962, 95, 2182.
5. (a) B. R. Baker, R. E. Schaub, J. P. Joseph, F. J. McEvoy and J. H. Williams, J. Org. Chem., 1952, 17, 164; (b) N. J. Leonard and M. J. Martell Jr., Tetrahedron Lett., 1960, 25, 44; (c) S. C. Bell and S. J. Childress, J. Org. Chem., 1962, 27, 1691; (d) T. Goto, Y. Kishi, S. Takahashi and Y. Hirata, Tetrahedron, 1965, 21, 2059.
6. (a) H. E. Zaugg and W. B. Martin, Org. React., 1965, 14, 52; (b) S. Kano, Y. Tanaka, S. Sugino and S. Hibino, Synthesis, 1980, 695; (c) Y. Tomioka, K. Ohkubo and M. Yamazaki, Chem. Pharm. Bull., 1985, 33, 1360.
7. M. Maikosza, A. J. Kinowski and S. Ostrowski, Synthesis, 1993, 1215.
8. K. Schofield and T. Swain, J. Chem. Soc., 1949, 1367.
9. T. Koyama, T. Hirota, F. Yagi, S. Ohmori and M. Yamata, Chem. Pharm. Bull., 1975, 23, 3151.
10. A. Bendich, P. J. Russell Jr. and J. J. Fox, J. Am. Chem. Soc., 1954, 76, 6073.
11. (a) J. Sarasin and E. Wegmann, Helv. Chim. Acta, 1924, 7, 713; (b) A. H. Cook and E. Smith, J. Chem. Soc., 1949, 2329, 3001; (c) G. Shaw and D. N. Butler, J. Chem. Soc., 1959, 4040; (d) R. N. Naylor, G. Shaw, D. V. Wilson and D. N. Butler, J. Chem. Soc., 1961, 4845; (e) K. Kadir, G. Shaw and D. Wright, J. Chem. Soc., Perkin Trans. 1, 1980, 2728; (f) K. E. Andersen and E. B. Pedersen, Liebigs Ann. Chem., 1985, 921; (g) P. R. Birkett, H. King, Ch. B. Chapleo, D. F. Ewing and D. Mackenzie, Tetrahedron, 1993, 49, 11029.
12. (a) S. Ostrowski, Synlett, 1995, 253; (b) S. Ostrowski, Heterocycles, 1996, 43, 389.
13. S. Ostrowski, in preparation.