Efficient Synthesis of Macrocyclic Dilactam Crown Ethers by Fast Addition Method

• Autorzy: Rahimzadeh M. , Eshghi H. , Rostami F. , Faghihi Z.
• Języki publikacji: EN

Abstrakty

EN

A simple and convenient method for preparing macrocyclic dilactam crown ethers containing N2O5, N3O3, N3O4, N3O5 and N2O10 donor atoms with 18-32 membered rings was developed. These compounds were obtained in the macrocyclization step under vigorous stirring conditions as well as fast addition of reactants. This step does not require external cyclization factors such as high dilution approach, template effect or nitrogen protection and provides the expected dilactams in high yields, ranging from 65-95%. The course of the reaction is assumed to depend on the occurrence of self assembly phenomena which are stimulated by a logic concentration in a selected solvent and the yields are improved by application of high speed stirring and fast addition of reactants.

Słowa kluczowe

EN

dilactam crown ethers; fast addition method; high dilution technique; macrocyclization; self-assembly

• Wydawca: Polskie Towarzystwo Chemiczne
• Czasopismo: Polish Journal of Chemistry
• Rocznik: 2005
• Tom: Vol. 79 / nr 1
• Strony: 73--81
• Opis fizyczny: Bibliogr. 29 poz., rys.

Twórcy

autor

Rahimzadeh M.

• Department of Chemistry, Ferdowsi University of Mashhad, Mashhad 91775-1436, Iran

autor

Eshghi H.

• Department of Chemistry, Ferdowsi University of Mashhad, Mashhad 91775-1436, Iran
• Department of Chemistry, Ferdowsi University of Mashhad, Mashhad 91775-1436, Iran

autor

Rostami F.

• Department of Chemistry, Ferdowsi University of Mashhad, Mashhad 91775-1436, Iran

autor

Faghihi Z.

• Department of Chemistry, Ferdowsi University of Mashhad, Mashhad 91775-1436, Iran

Bibliografia

• 1. Collins T.J., Kostka K.L., Munck E. and Ufielman E.S., J. Am. Chem. Soc., 112, 5637 (1990).
• 2.Kimura E., Pure Appl. Chem., 61, 823 (1989).
• 3. Kimura E., Kurogi Y., Wade S. and Shionoya M., J. Chem. Soc. Chem. Commun., 781 (1989).
• 4. Attiyat A.S., Kadry A.M., Hanna H.R., Ibrahim Y.A. and Christian G.D., Anal. Sci. (Japan), 6, 21 (1990).
• 5. Attiyat A.S., Ibrahim Y.A., Kadry A.M., Xie R.Y., Christian G.D. and Fresenius Z., Anal. Chem., 329, 12 (1987).
• 6. Krakowiak K.E., Bradshaw J.S. and Izatt R.M., .1. Org. Chem., 55, 3364 (1990).
• 7. Krakowiak K.E., Bradshaw J.S., Izatt R.M. and Zamecka-Krakowiak D.J., Tetrahedron Lett., 31,1077 (1990). .
• 8. Krakowiak K.E., Bradshaw J.S. and Izatt R.M., .1. Heterocyclic Chem., 27, 1585 (1990).
• 9. Bradshaw J.S., Krakowiak K.E., An H. and Izatt R.M., .1. Heterocyclic Chem., 27, 2113 (1990).
• 10. Petranek J. and Ryba O., Collect. Czech. Chem. Commun., 48, 1944 (1983).
• 11.Dietrich B., Lehn J.M. and Sauvage J.P., Tetrahedron Lett., 2885 (1969).
• 12. Dietrich B., Lehn J.M. and Sauvage J.P., Tetrahedron, 29, 1629 (1973).
• 13.Nagao Y., Seno K., Miyasaka T. and Fujita B., Chem. Lett., 159 (1980).
• 14. Sharghi H. and Eshghi H., Tetrahedron, s1, 913 (1995).
• 15. Sharghi H. and Eshghi H., .1. Sci. I. R Iran, 9, 238 (1998); C‘. A., 132, 1225931: (2000).
• 16. Ibrahim Y.A. and Elwahy A.H.M., Synthesis, 503 (1993).
• 17. Markovich I.S., Filyagina N.A., Dziomko V.M., Ryabokobylko Y.S., Adamova G.M. and Zelichenok S.L.,Khim. Geterotsikl. Soedin, 185 (1983).
• 18. Biemat J.F., Jereczek E. and Bujewski A., Polish.J. Chem., 53, 2367 (1979); Biernat J.F. and Luboch E., Tetrahedron, 40, 1927 (1984).
• 19. Hogberg S.A.G. and Cram C.J., .J. Org. Chem., 40, 151 (1975).
• 20. ShamsipurM., Fakhari A.R., Sharghi H., Eshghi H. and Ganjali M.R., Polish J. Chem., 76, 1665 (2002).
• 21. Shamsipur M., Rouhani S., Ganjali M.R., Sharghi H. and Eshghi H., Sensors and Actuators B, 59, 30 (1999).
• 22. Shamsipur M., Rouhani S., Ganjali M.R., Eshghi H. and Sharghi H., Microchem. J., 63, 202 (1999).
• 23. Shamsipur M., Rouhani S., Sharghi H., Ganjali M.R. and Eshghi H., Anal. Chem., 71, 4938 (1999).
• 24. Sharghi H., Massah A.R., Eshghi H. and Niknam K., .1. Org. Chem., 63, 1455 (1998); Sharghi H., Niknam K. and Pooyan M., Tetrahedron, 57, 6057 (2001).
• 25. Sharghi H., Nasseri M.A. and Niknam K., .J. Org. Chem., 66, 7287 (2001).
• 26. Gibb C.L.D. and Gibb B.C., .1. Supramolecular Chem., 1, 39 (2001); Gibb C.L.D., Stevens E.D. and Gibb B.C., Chem. Commun., 363 (2000).
• 27. Sherrington D.C. and Taskinen K.A., Chem. Soc. Rev., 30, 83 (2001).
• 28. MacGillivary L.R. and Atwood J.L., Angew. Chem. Int. Ed., 38, 1018 ( 1999).
• 29. Corbin P.S. and Zimmerman S.C., .J Am. Chem. Sac., 120, 9710 (1998).