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DOI: 10.1039/A806439C (Paper) Reference Section for: J. Chem. Res. (S), 1999, 430-431

Synthesis of 2,3,4,6-Tetrasubstituted Pyridines as Precursors to Bicycles and Polycycles

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Fathi A. Abu-Shanab

Abstract

Ammonium 1,1,3-tricyano-2-methylprop-2-enide 1a and sodium 2-amino-1,1,3-tricyanoprop-2-enide 1b are treated with H2S in absolute ethanol to afford 3,4,6-trisubstituted pyridine-2(1H)-thione 3a,b; their structures are confirmed by reaction with phenacyl bromide to give 4a,b; also 3a,b reacts with DMFDMA to give 6a,b, and on treatment of 6a with phenacyl bromide affords 8; reaction of 4b with DMFDMA gave 9 while methylation of 3a,b by methyl iodide in ethanolic sodium hydroxide gives 10a,b.

References

  1. V. P. Litvino, L. A. Rodinovskaya, Yu. A. Sharanin, A. M. Shestopalov and A. Senning, Sulfur Rep., 1992, 13, 155 Search PubMed.
  2. A. M. Shestopalov, V. K. Promomenkov, Yu. A. Sharanin, L. A. Rodinovskaya and S. Yu. Sharanin, Zh. Org. Khim., 1984, 20, 1517 CAS.
  3. A. M. Shestopalov, V. K. Promomenkov, Yu. A. Sharanin and A. M. Shestopalov, Enaminocarbonyl Compounds in Synthesis of 3-cyano-2(1H)-pyridinethiones, in Itogi Nauki i Techniki, Ser. Organicheskaya Khimiya, ed. Kabachnie, VINITI, Moscow, 1989, vol. 17, pp. 72–156 and references therein Search PubMed.
  4. G. E. Elgemeier, M. M. Sallam, M. S. Sherif and M. H. Elnagdi, Heterocycles, 1985, 23, 3107.
  5. F. M. A. Galil, M. M. Sallam, M. S. Sherif and M. H. Elnagdi, Liebigs Ann. Chem., 1986, 1639 CAS.
  6. U. Schmidt and H. Kubitzek, Chem. Ber., 1960, 93, 1559 CAS.
  7. H. Vieweg, S. Leistner and G. Wagner, Pharmazie, 1986, 41.
  8. F. A. Abu-Shanab, A. D. Redhouse, J. R. Thompson and B. J. Wakefield, Synthesis, 1995, 557 CrossRef CAS.
  9. F. A. Abu-Shanab, F. A. Ali and B. J. Wakefield, Synthesis, 1995, 923 CrossRef CAS.
  10. D. Briel, S. Dumke, G. Wagner and B. Olk, J. Chem. Res., 1991, (S) 178; (M) 1841 Search PubMed.
  11. F. A. Abu-Shanab, M. H. Elnagdi, F. A. Ali and B. J. Wakefield, J. Chem. Soc., Perkin Trans. 1, 1994, 1449 RSC.
  12. A. W. Erian, Chem. Rev., 1993, 93, 1991 CrossRef CAS and references therein.
  13. D. H. Williams and I. Fleming, Spectroscopic Methods in Organic Chemistry, McGraw-Hill, London, 4th edn., 1987 Search PubMed.
  14. K. Gewald, Chimia, 1980, 34, 101 CAS and references therein.
  15. H. Sliwa, D. Blondeau and R. Rydzkowsk, J. Heterocycl. Chem., 1983, 20, 1613 CAS.
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