Reaction of (2-Ethyl-aziridin-2-yl)diphenyl Methanol and Diphenyl-(2-phenyl-aziridin-2-yl)methanol with Phenyl and t-Butyl Isocyanates, Phenyl Isothiocyanate and Thiophosgene

Kryczka, B.; Leśniak, S.; Pasternak, B.; Porwański, S.

Artykuł - szczegóły

Tytuł artykułu

Reaction of (2-Ethyl-aziridin-2-yl)diphenyl Methanol and Diphenyl-(2-phenyl-aziridin-2-yl)methanol with Phenyl and t-Butyl Isocyanates, Phenyl Isothiocyanate and Thiophosgene

Autorzy

Kryczka B. , Leśniak S. , Pasternak B. , Porwański S.

Identyfikatory

Warianty tytułu

Języki publikacji

Abstrakty

The reactions of aziridine alcohols with organic isocyanates, isothiocyanates and thiophosgene were described. It was found that the reactions with phenyl or t-butyl isocyanate give urea derivatives as major products, whereas the reaction with thiophosgene resulted in the formation of isothiocyanates derivatives. The mecha - nism of these reactions was proposed.

Słowa kluczowe

ziridinyl alcohols isocyanates isothiocyanates thiophosgene urea derivatives

Wydawca

Polskie Towarzystwo Chemiczne

Czasopismo

Polish Journal of Chemistry

Rocznik

2007

Tom

Vol. 81, nr 11

Strony

1927--1934

Opis fizyczny

Bibliogr. 33 poz., rys.

Twórcy

autor

Kryczka B.

autor

Leśniak S.

autor

Pasternak B.

autor

Porwański S.

Institute of Chemistry, University of Łódź, Narutowicza 68, PL 90-136 Łódź, Poland

Bibliografia

1. Aziridines and Epoxides in Organic Synthesis, Ed. Yudin A.K, Wiley-VCH Verlag GmbH & Co. KgaA, Weinheim 2006.
2. Atkinson R.S., Tetrahedron, 55,1519 (1999).
3. Zwanenburg B., Pure Appl. Chem., 71, 423 (1999).
4. Osborn H.M.I, and Sweeney J., Tetrahedron: Asym., 8, 1693 (1997).
5. McCoull M. and Davis F.A., Synthesis, 1347 (2000).
6. Cardillo G., Gentilucci L. and Tolomelli A., Aldrichimica Acta, 36, 39 (2003).
7. Hu X.E., Tetrahedron, 60,2701 (2004).
8. Tanner D., Pure Appl. Chem., 65 1319 (1994)
9. Tanner D., Angew. Chem. Int Ed. Engl, 33, 599 (1994).
10. Sweeney J.B., Chem. Soc. Rev., 31,247 (2002).
11. Bestian H., Justus Liebigs Ann. Chem., 566, 210 (1950).
12. Weber F.G., Liepert H. And Köppel H., J. Prakt. Chem., 328, 612 (1986).
13. Iyengar B.S., Dorr R.T., Alberts D.S., Hersh E.M., Ewan M., Salmon S.E. and Ramers W.A., J. Med. Chem., 42, 510(1999).
14. Archer D.A. and Singer B.W., J. Chem. Soc. Perkin Trans. 1, 2844 (1976).
15. Benhaoua H., Texier F. and Carrie R., Tetrahedron, 42, 2283 (1986).
16. Nadir U.K. and Basu N., Tetrahedron, 49, 7787 (1993).
17. Butler D.C.D., Inman G.A. and Alper H., J. Org. Chem., 65, 5887 (2000).
18. Trost B.M. and Fandrick D.R., J. Am. Chem. Soc., 125, 11836 (2003).
19. Dong Ch. and Alper H., Tetrahedron Asym., 15, 1537 (2004).
20. Trost B.M. and Fandrick D.R.,Org. Lett., 5, 823 (2005).
21. Tisler M., Arch. Pharm., 291, 457 (1958).
22. Deutsh A.S. and Fanta P.E., J. Org. Chem., 21, 892 (1956).
23. Weber F.G., Marrek M., Redeglia R. and Köppel H., J. Prakt. Chem., 331, 665 (1989).
24. Lown J.W., Dallas G. and Maloney T.W., Can. J. Chem., 47, 3557 (1969).
25. Tomalia D.A., J. Heterocycl. Chem., 3, 384 (1966).
26. Bartnik R., Diab Y. and Laurent A., Tetrahedron, 33, 1279 (1977).
27. Baret P., Bourgeois M., Gey C. and Pierre J.-L., Tetrahedron, 35, 189 (1979).
28. Laurent A., Marsura A. and Pierre J.-L., J. Heterocycl. Chem., 17, 1009 (1980).
29. Bartnik R., Cebulska Z., Orłowska B., Faure R., Laurent A. and Loiseleur H., Bull. Soc. Chim. Fr., 397 (1986).
30. Bartnik R., Cebulska Z., Laurent A. and Orłowska B., J. Chem. Res., (M), 0112 (1986).
31. Golovko V.V., Statsenskaya A.I., Baskakov Yu.A. and Putsykin Yu.G., Khim. Getrotsikl. Soedin., 22, 1339(1986).
32. Wagner P.J., Zhou B., Hasegawa T. and Ward D.L., J. Am. Chem. Soc., 113, 9640 (1991).
33. KatritzkyA.R. and Qi M., J. Org. Chem., 62, 4116 (1997).

Typ dokumentu

Bibliografia

Identyfikator YADDA

bwmeta1.element.baztech-article-BUJ5-0017-0026