REaction of N-Arylbenzamidines with Arenenitrile N-Oxides

• Autorzy: Szczepankiewicz W. , Borowiak T. , Kubicki M. , Suwiński J. , Wagner P.
• Języki publikacji: EN

Abstrakty

EN

Looking for a method of 4-arylamino-4-aryl-3-aza-3-buten-2-one oximes preparation a reaction of N-arylbenzamidines with arenenitrile N-oxides (generated in situ form oximoyl chlorides) has been performed to produce unstable 5-amino-4,5-dihydro-1,2,4-oxadiazoles,which under aqueous acidic conditions hydrolyzed to acyclic N-benzoyloxy-N'-arylareneamidines. Structure of one of the latter compounds has been confirmed by X-ray analysis.

Słowa kluczowe

EN

synthesis; oximoyl chlorides; amidines; nitrile N-oxides; X-ray

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Polish Journal of Chemistry
• Rocznik: 2002
• Tom: Vol. 76 / nr 8
• Strony: 1137--1142
• Opis fizyczny: Bibliogr. 13 poz., rys.

Twórcy

autor

Szczepankiewicz W.

• Institute of Organic Chemistry and Technology, Silesian University of Technology, Krzywoustego 4, 44-100 Gliwice, Poland

autor

Borowiak T.

• Faculty of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, 60-780 Poznań, Poland

autor

Kubicki M.

• Faculty of Chemistry, Adam Mickiewicz University, Grunwaldzka 6, 60-780 Poznań, Poland

autor

Suwiński J.

• Institute of Organic Chemistry and Technology, Silesian University of Technology, Krzywoustego 4, 44-100 Gliwice, Poland

autor

Wagner P.

• Institute of Organic Chemistry and Technology, Silesian University of Technology, Krzywoustego 4, 44-100 Gliwice, Poland

Bibliografia

• 1. (a) Fry D.W., Kraker A.J., McMichael A., Ambroso L.A.,NelsonI.M., Leopold W.R., Connors R.W. and Bridges A.J., Science, 265, 1093 (1994).(b) Hennequin L.F., Thomas A.R, Johnstone C., Stokes E.S.E., Pie P.A., Lohman J-J.M., Oglivie D.J., Dukes M., Wedge S.R., Curwen J.O., Kendrew J. and Brempt C., J. Med. Chem., 42, 5369 (1999). (c) Smaill J.B., Rawcastle G.W., Loo J.A., Greis K.D., Cahn O. H., Reyner E.L., Lipka E., Showalter H. D.H., Vincent P.W., Elliott W.L. and Denny W.A., J. Med. Chem., 43, 1380 (2000). (d) Wright S.W., Hageman D.L., McClure L.D., Carlo A.A., Treadway J.L., Mathiowetz A.M., Withka J.M. and Bauer P.H., Bioorg. Med. Chem. Lett., 11, 17 (2001).
• 2. Lange N.A. and Sheibley F.E., J. Am. Chem. Soc., 53, 3867 (1931).
• 3. Armarego W.L., Heterocyclic Compounds, Fused Pyrimidines, Part I, Quinazolines, NY 1967, p. 222.
• 4. (a) Szczepankiewicz W. and Suwiński J., Tetrahedron Lett., 39,1785 (1998). (b) Szczepankiewicz W., Suwiński J. and Bujok R., Tetrahedron, 56, 9343 (2000).
• 5. Suwiński J. and Mohamed M.A.A., Polish J. Chem., 75, 965 (2001).
• 6. Szczepankiewicz W., Suwiński J. and Słowikowska J., Acta Cryst., Sect. C, 55,2158 (1999).
• 7. Oxley P., Partridge M.W. and Short W.F., J. Chem. Soc., 1110(1947).
• 8. Rajagopalan P., Advani B.G. and Talaty C.N., Org. Synth,, Coll. Vol. J, 504 (1973).
• 9. El-Abdellah M.M., Nazer M.Z. Hussein A.Q. Awadallah A.M., Rademacher P. and Woydt M., J. Heterocycl. Chem., 28, 1229 (1991).
• 10. Kuma CrysAlis CCD program system, Kuma Diffraction, Wroclaw, Poland, 1990.
• 11. Kuma CrysAlis RED program system, Kuma Diffraction, Wroclaw, Poland, 1990.
• 12. Sheldrick G.M, Acta Cryst. Sect. A, 46, 467 (1990).
• 13. Sheldrick G.M., Program for the Refinement of Crystal Structures, University of Gottingen, Germany, 1993