Synthesis of the N-Allylthioamide Derivatives of Cyclic Oxo- and Dioxo- Acids and Their Cyclization to the Derivatives of 4,5-Dihydrothiazole

• Autorzy: Wesołowska, A. , Jagodziński, T. S. , Sośnicki, J. G. , Hansen, P. E.
• Języki publikacji: EN

Abstrakty

EN

The title N-allylthioamides (1a-f) were synthesized in the reaction of allyl isothiocyanate with enamines (1a-c) and 1,3-diketones (1d-f), respectively, carried out in an acetonitrile solution in the presence of DBU. When treated with the bromine-dioxane complex or with iodine, they underwent cyclization to the corresponding derivatives of 4,5-dihydrothiazole (2a-g). NMR spetroscopy made it possible to elucidate the tautomeric structures of the thioamides and thiazolines.

Słowa kluczowe

EN

4,5-dihydrothizole; N-allylthioamides

• Czasopismo: Polish Journal of Chemistry
• Rocznik: 2001
• Tom: Vol. 75, nr 3
• Strony: 387-400
• Opis fizyczny: Bibliogr. 17 poz., rys.

Twórcy

autor

Wesołowska, A.

• Department of Organic Chemistry, Technical University of Szczecin, 71-065 Szczecin, Aleja Piastów 42, Poland

autor

Jagodziński, T. S.

• Department of Organic Chemistry, Technical University of Szczecin, 71-065 Szczecin, Aleja Piastów 42, Poland

autor

Sośnicki, J. G.

• Department of Organic Chemistry, Technical University of Szczecin, 71-065 Szczecin, Aleja Piastów 42, Poland

autor

Hansen, P. E.

• Department of Life Sciences and Chemistry, Roskilde University, P.O.Box 260, DK-4000 Roskilde, Denmark

Bibliografia

• 1. Smith P.A.S. and Sulivan J.M., J. Org. Chem.. 26, 1132(1961).
• 2. Engman L., J. Org. Chem., 56, 3425 (1991).
• 3. Just G. and Rossy P., J. Org. Chem., 38,624 (1973).
• 4. Ershova I.I., and Staninets I., Dokł. Akad. Nauk Ukr. SSR., Ser.B, 1097 (1975).
• 5. Takahata H., Takamatsu T„ Mozumi M., Chen Y., Yamazaki T, and Aoe K., J. Chem. Soc., Chem. Com., 1627(1987).
• 6. Takahata H, Takamatsu T. and Yamazaki T,, J. Org. Chem., 54, 4812 (1989).
• 7. Takahata H., Takamatsu T., Chen Y„ Ohkubo N., Yamazaki T. and T.Momose, J. Org. Chem.. 55, 3792 (1990).
• 8. Takahata 11., Yamazaki K.,Takamatsu T., Yamazaki T. and Momose T., J. Org. Chem., 55,3947(1990).
• 9. Takahata H., Wang E-C., Ikuro K., Yamazaki T. and Momose T., Heterocvcles. 34,435 (1992).
• 10. Jagodziński T.S., Sośnicki J.G. and Nowak-Wydra B., Polish J. Chem.. 67, 1043 (1993).
• 11. Hansen P.E., Duus F., Neumann R., Wesołowska A., Sośnicki J. and Jagodziński T., Polish J. Chem.. 74, 409 (2000).
• 12. Bauer W. and Kuhlein K., in Houben-Weyll „Methoden der Organischen Chemie ”, Ed. George Thieme Verlag, Stuttgard, NY 1985, E5 pp. 1218-1275, and references therein.
• 13. Yanovskaya L.A. and Terentiev A.P., Zh. Obsch. Khim.. 22, 1594(1952).
• 14. Jagodziński T.S., Sośnicki J.G. and Królikowska M, Heterocyclic Comm.. 1, 353 (1995).
• 15. Hansen P.E., Duus F., Bolvig S. and Jagodziński T.S., J. Mol. Struct., 378, 45 (1996).
• 16. Anulewicz R., Krygowski T.M. and Jagodziński T.S., Polish J. Chem., 72, 439 (1998).
• 17. Bolvig A. and Hansen P.E., Magn. Reson. Chem., 34,467 (1996).