Synthesis of 4,5-Dicyanoimidazoles

• Autorzy: Bukowska M. , Prejzner J. , Szczeciński P.
• Języki publikacji: EN

Abstrakty

EN

The effective procedure of preparation of 2-trifluoromethyl-4,5-dicyanoimidazole (3a) from diaminomaleonitrile (1) and trifluoroacetic anhydride has been elaborated. The syntheses of five other 2-substituted imidazoles from appropriate acyl derivatives of 1 have been attempted. Out of them only 4,5-dicyanoimidazole (3b) could be obtained in good yield.

Słowa kluczowe

EN

imidazole; cyclization; diaminomaleonitrile

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Polish Journal of Chemistry
• Rocznik: 2004
• Tom: Vol. 78 / nr 3
• Strony: 417--422
• Opis fizyczny: Bibliogr. 12 poz., rys.

Twórcy

autor

Bukowska M.

• Warsaw University of Technology, Faculty of Chemistry, Noakowskiego 3, 00-664 Warszawa, Poland

autor

Prejzner J.

• Warsaw University of Technology, Faculty of Chemistry, Noakowskiego 3, 00-664 Warszawa, Poland

autor

Szczeciński P.

• Warsaw University of Technology, Faculty of Chemistry, Noakowskiego 3, 00-664 Warszawa, Poland

Bibliografia

• 1. Begland R.W., Hartter D.R., Jones F.N., Sam D.J., Sheppard W.A., Webster O.W. and Weigert W.A., J. Org. Chem., 39, 2341 (1974).
• 2. Booth B.L., Pritchard R. and Proenca M.F., Synthesis-Stuttgart, (9) 1269 (2000).
• 3. Johnson D.M. and Rasmussen P.G., Macromolecules, 33(23), 8597 (2000).
• 4. Ohtsuka Y„ J. Org. Chem., 41, 629 (1976).
• 5. Woodward D.W., U.S. Patent 2534331 (1950); C.A. 45, 5191 (1951).
• 6. O’Connell J.F., Parquette J., Yelle W.E., Wang W. and Rapoport H., Synthesis, 767 (1988).
• 7. Johnson S.J., Synthesis, 75 (1991).
• 8. Al-Azmi A., Elassar A.Z.A. and Booth B.L., Tetrahedron, 59(16), 2749 (2003).
• 9. Bredereck H. and Schmotzer G., Liebigs Ann. Chem., 600, 95 (1956).
• 10. Sheppard W.A. and Webster O.W., J. Am. Chem. Soc., 95,2695 (1973).
• 11. Ohtsuka Y.,J. Org. Chem., 41, 713 (1976).
• 12. Drakenberg T. and Forsen S., J. Phys. Chem., 74, 1 (1970).