Synthesis and Transformation of 1-Monosubstituted Tetrazoles to Pyrimidinones, Benzoxazoles and Quinazolinediones Through 1,4-Disubstituted Tetrazolium Salts

• Autorzy: Voitekhovich S. , Gaponik P. N. , Lyakhov A. S. , Ivashkevich O. A.
• Języki publikacji: EN

Abstrakty

EN

Synthesis and some new transformations of 1-aryltetrazoles into other heterocycles through 1,4-disubstituted tetrazolium salts are described. 1-Aryltetrazoles, quaternized with tert-butanol and diacetone alcohol in perchloric acid media, gave pure 1,3- or 1,4-disubstituted tetrazolium salts or their mixtures. 1,3-Disubstituted tetrazolium salts are slowly converted into the corresponding 1,4-salts under dissolving in perchloric acid. 1,4-Disubstituted tetrazolium salts are recyclized to 2-alkylaminobenzoxazoles, 3-monosubstituted 2,4-quinazolinediones and mixtures of di- and tetrahydropyrimidin-2(1H)- ones in basic conditions.

Słowa kluczowe

EN

tetrazoles; quaternization; tetrazolium salts; 2-aminobenzoxazoles; 2,4-quinazolinediones; dihydropyrimidin-2(1H)-one; tetrahydropyrimidin-2(1H)-one; crystal structure

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Polish Journal of Chemistry
• Rocznik: 2001
• Tom: Vol. 75, nr 2
• Strony: 253--264
• Opis fizyczny: Bibliogr. 29 poz., rys.

Twórcy

autor

Voitekhovich S.

• Research Institute for Physical Chemical Problems of the Belarussian State University, 14 Leningradskaya str., 220050 Minsk, Belarus

autor

Gaponik P. N.

• Research Institute for Physical Chemical Problems of the Belarussian State University, 14 Leningradskaya str., 220050 Minsk, Belarus

autor

Lyakhov A. S.

• Research Institute for Physical Chemical Problems of the Belarussian State University, 14 Leningradskaya str., 220050 Minsk, Belarus

autor

Ivashkevich O. A.

• Research Institute for Physical Chemical Problems of the Belarussian State University, 14 Leningradskaya str., 220050 Minsk, Belarus

Bibliografia

• 1. Butler R.N., “Tetrazoles'’ in: Comprehensive Heterocyclic Chemistry II, (A.R. Katritzky, C.W. Rees, E.F.V. Scriven eds.), Pergamon Press, Oxford, vol. 4, p. 621 (1996).
• 2. Koldobskii G.I. and Ostrovskii V.A., Usp. Khim., 63, 847 (1994).
• 3. Gaponik P.N., “Synthesis and Properties ofN-Substituted Tetrazoles” in: Chemical problems of development of new materials and technologies, (V.V. Sviridov ed.), Belarussian State University Minsk p 185 (1998).
• 4. Wirsehun W., Winkler M., Lutz K. and Jochims J.C., J. Chem. Soc. Perkin 1, 1755, (1998).
• 5. Gaponik P.N., Grigoriev Y.V., AndreevaT.N. and MarudaI.I., Khim Geterotsikl. Soedin., 915 (1995).
• 6. Gaponik P.N., Voitekhovich S.V., Manida I.I., Kulak A.A. and Ivashkevich O.A., Polish J Chem 72, 2247 (1998).
• 7. Gaponik P.N., Voitekhovich S.V., Lyakhov A.S. and Maruda I.I., Khim.Geterotsikl Soedin 1222 (1999).
• 8. Boev V.l., Krasnikova E.M., Moskalenko A.I., Pilko E.I., Snegur L.V., Babin V.N. and Nekrasov Y.S., Zh. Obshch. Khim., 67, 1386 (1997).
• 9. Araki S., Yamamato K., Yagi M., Inone T., Fukagawa H., Hattori H., Yamamura H., Kawai M. and Butsugan Y., Eur.Org. Chem., 121 (1998).
• 10. Lowack H. and Weiss R., J. Am. Chem. Soc., 112, 333 (1990).
• 11. Zimmerman M. and Olofson R.A., Tetrahedron Lett., 3453 (1970).
• 12. Quast H. and Hergenrother T., Lieb. Ann. Chem., 581 (1992).
• 13. Gaponik P.N., Karavai V.P. and Grigoriev Y.V.. Khim. Geterotsikl. Soedin., 1521 (1985).
• 14. Gaponik P.N., Karavai V.P., Davshko I.E., Degtyarik M.M. and Bogatikov A.N., Khim. Geterotsikl. Soedin., 1528(1990).
• 15. Grigoriev YV., Maruda 1.1, and Gaponik P.N., Izv, AN Belarus!, Ser. Khim., 86 (f 997). Chem. Abs., 128, 217333g (1998).
• 16. Ivashkevich O.A., Gaponik P.N., Koren A.O., Bubel O.N. and Fronchek E.V., Int. J. Quant. Chem., A3, 813 (1992).
• 17. Naumenko V.N., Koren A.O. and Gaponik P.N., Magn. Res. Chem., 30, 558 (1992).
• 18. Gaponik P.N., Ivashkevich O.A., Naumenko V.N., Kovalyova T.B., Andreeva T.N. and Koren A.O., Spectrochim. Acta, 49A, 135 (1993).
• 19. OlofsonR.A.,Thompson W.R., Henry R.A. andMichelman J.S., J.Am. Chem. Soc., 86,1865(1964),
• 20. Mikołajczyk M. and Kielbasiński P., Tetrahedron. 37,233 (1981).
• 21. Wagner K., FindeisenK,, Schafer W, and Werner D,,Angew. Chem,, 93, 855 (1981).
• 22. Gadekar S.M., Kotsen A.M. and Cohen E., J. Org. Chem., 29,4666 (1964).
• 23. Kashima C., Katoh A., Yokota Y. and Omotc Y., J. Chem. Soc. Perkin I, 489 (1981).
• 24. Brown D.J., “Pyrimidines and their Benzo Derivatives” in: Comprehensive Heterocyclic Chemistry, (A.R. Katritzky, C.W. Rees eds.), Pergamon Press, Oxford, vol. 3, pt. 2B, p. 57 (1984).
• 25. Whiting J.E. and Edward J.T., Can. J. Cliem,, 49, 3798 (1971).
• 26. Llinares J., Gały J.P ., Faure R., Vincent E.J. and Elguero J., Can. J. Chem., 57, 937 (1979).
• 27. Davidkov K., Galabov V. and Simov D., Izv. Khim. Bulg. AN., 12,424 (1979).
• 28. Allen F.H. and Kennard O., Chemical Design Automation News, 8, 31 (1993).
• 29. Sheldrick G.M., Program for crystal structure refinement, University of Goettingen, 1997; Sheldrick G.M.. Acta Cryst., A46, 467 (1990); Sheldrick G.M., Dauter Z„ Wilson K.S., Hope H. and Sieker L., Acta Cryst., D49,18 (1993).