Free accessResearch articleFirst published online 1999-3
Studies on Uracils: Synthesis of Tetrazolo[4’,5':1,6]pyrido[2,3- d ]pyrimidines by the Action of Cyano Stabilised Carbanions on 6-Azido-5-formyluracils †
6-Azido-5-formyluracils 2 undergo base catalysed condensation with cyanocarbanions to yield tetrazolo[4’,5':1,6]-pyrido[2,3-d]pyrimidines 4 in good yields.
References
1.
(a) LuntE., Comprehensive Organic Chemistry, ed. BartonD., and OllisW. D., Pergamon Press, Oxford, 1974, vol. 4, p. 493; (b) J. D. Brown, Comprehensive Heterocyclic Chemistry, ed. KatritzkyA. R., and ReesC. W., Pergamon Press, Oxford, 1984, vol. 3, p. 57; (c) T. Sasaki, K. Minamoto, T. Suzuki and S. Yamashita, Tetrahedron, 1980, 36, 865; (d) T. K. Bradshaw and D. W. Hutchison, Chem. Soc. Rev., 1977, 6, 43; (e) P. J. Bhuyan, R. C. Boruah and J. S. Sandhu, J. Org. Chem., 1990, 55, 568; (f) P. J. Bhuyan, J. S. Sandhu and A. C. Ghosh, Tetrahedron Lett., 1996, 37, 1853 and references therein.
2.
(a) MarumotoR., and FurukawaY., Chem. Pharm. Bull., 1977, 25, 2974; (b) C. C. Cheng and B. Roth, Prog. Med. Chem., 1971, 8, 61; (c) E. D. Clercq and R. Bernaerts, J. Biol. Chem., 1987, 262, 14905; (d) A. S. Jones, J. R. Swgers, R. T, Walker and E. D. Clercq, J. Med. Chem., 1988, 31, 268.
3.
(a) BabaM., PauwelsR., HerdwigP., ClercqE. D., DesmysterJ., and VandepulfeM., Biochem. Res. Commun., 1957, 142, 128; (b) E. D. Clercq, J. Med. Chem., 1986, 29, 1561.
4.
(a) ClercqE. D., Anticancer Res., 1986, 6, 549; (b) A. S. Jones, G. Verhalst and R. T. Walker, Tetrahedron Lett., 1974, 4415.
5.
(a) TennantG., J. Chem. Soc. C, 1966, 2290; (b) D. R. Sutherland and G. Tennant, J. Chem. Soc., Perkin Trans. 1, 1974, 534; (c) C. Westerlund, J. Heterocycl. Chem., 1980, 17, 1765; (d) R. K. Smalley and M. Teguiche, Synthesis, 1990, 654.
6.
PorterT. C., SmalleyR. K., TeguicheM., and PurwonoB., Synthesis, 1997, 773.
7.
PrajapatiD., BhuyanP. J., and SandhuJ. S., J. Chem. Soc., Perkin Trans. 1, 1988, 607.