Synthesis of New meso-Substituted Heterocyclic Calix[4]arenes via SN H Approach

Mikhail V. Varaksin,^a,b Irina A. Utepova,^a,b Oleg N. Chupakhin,^a,b@and Valery N. Charushin^a,^b

^aUral Federal University, 620002 Ekaterinburg, Russia

^bInstitute of Organic Synthesis, Ural Branch of the RAS, 620041 Ekaterinburg, Russia

^@Corresponding author E-mail: chupakhin@ios.uran.ru

DOI: 10.6060/mhc131268c

Macroheterocycles 2013 6(4) 308-314

An effective synthetic approach to novel heterocyclic derivatives of meso-substituted calix[4]arenes has been suggested by using the S_N^H methodology.

References

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1. Steed J.W., Atwood J.L. Supramolecular Chemistry, 2nd edn. Chichester: John Wiley & Sons, 2009.
http://dx.doi.org/10.1002/9780470740880

2. Asfari M.Z., Bőhmer V., Harrowfield J., Vicens J. Calixarenes. Dordrecht: Kluwer Academic, 2001.

3. Kalchenko V.I. Pure Appl. Chem. 2008, 80, 1449-1458.
http://dx.doi.org/10.1351/pac200880071449

4. Simoes J.B., da Silva D.L., de Fatima A., Fernandes S.A. Curr. Org. Chem. 2012, 16, 949-971.
http://dx.doi.org/10.2174/138527212800194746

5. Kim H.J., Lee M.H., Mutihac L., Vicens J., Kim J.S. Chem. Soc. Rev. 2012, 41, 1173-1190.
http://dx.doi.org/10.1039/c1cs15169j

6. Lo P.K., Wong M.S. Sensors 2008, 8, 5313-5335.
http://dx.doi.org/10.3390/s8095313

7. Iqbal K.S.J., Cragg P.J. Dalton Trans. 2007, 26-32.
http://dx.doi.org/10.1039/b613867p

8. Okunola O.A., Seganish J.L., Salimian K.J., Zavalij P.Y., Davis J.T. Tetrahedron 2007, 63, 10743-10750.
http://dx.doi.org/10.1016/j.tet.2007.06.124

9. Hennrich G., Murillo M.T., Prados P., Song K., Asselberghs I., Clays K., Persoons A., Benet-Buchholzc J., de Mendozac J. Chem. Commun. 2005, 2747-2749.
http://dx.doi.org/10.1039/b502045j

10. Andr S., Sansone F., Kaltner H., Casnati A., Kopitz J., Gabius, H.-J., Ungaro R. ChemBioChem. 2008, 9, 1649-1661.
http://dx.doi.org/10.1002/cbic.200800035

11. Mandolini L., Ungaro R. Calixarenes in Action. London: Imperial College Press, 2000.

12. Baklouti L., Vicens J., Harrowfield J. Calixarenes in the Nanoworld. Dordrecht: Springer, 2007.

13. Parker D. Macrocycle Synthesis. Oxford: Oxford University Press, 1996.

14. Sliwa W., Deska M. Arkivoc 2011, 1, 496-551.
http://dx.doi.org/10.3998/ark.5550190.0012.110

15. Harvey P.D. Coord. Chem. Rev. 2002, 233-234, 289-309.
http://dx.doi.org/10.1016/S0010-8545(02)00199-6

16. Scully P.A., Hamilton T.M., Bennett J.L. Org. Lett. 2001, 3, 2741-2744.
http://dx.doi.org/10.1021/ol016346b

17. Fischer C., Seichter W., Weber E. Beilstein J. Org. Chem. 2011, 7, 1602-1608.
http://dx.doi.org/10.3762/bjoc.7.188

18. Fischer C., Gruber T., Seichter W., Weber E. Org. Biomol. Chem. 2011, 9, 4347-4352.
http://dx.doi.org/10.1039/c1ob00028d

19. Fischer C., Stapf M., Seichter W., Weber E. Supramol. Chem. 2013, 25, 371-383.
http://dx.doi.org/10.1080/10610278.2013.783918

20. Sliwa W., Deska M. Arkivoc 2012, 1, 173-210.
http://dx.doi.org/10.3998/ark.5550190.0013.106

21. Hertel M.P., Behrle A.C., Williams S.A., Schmidt J.A.R., Fantini J.L. Tetrahedron 2009, 65, 8657-8667.
http://dx.doi.org/10.1016/j.tet.2009.08.033

22. Gruner M., Fischer C., Gruber T., Weber E. Supramol. Chem. 2010, 22, 256-266.
http://dx.doi.org/10.1080/10610270903437044

23. Gruber T., Gruner M., Fischer K., Seichter W., Bombicz P., Weber E. New J. Chem. 2010, 34, 250-259.
http://dx.doi.org/10.1039/b904489b

24. Fischer C., Katzsch F., Weber E. Tetrahedron Lett. 2013, 54, 2874-2877.
http://dx.doi.org/10.1016/j.tetlet.2013.03.101

25. Carroll L.T., Hill P.A., Ngo C.Q., Klatt K.P., Fantini J.L. Tetrahedron 2013, 69, 5002-5007.
http://dx.doi.org/10.1016/j.tet.2013.04.010

26. Joule J.A., Mills K. Heterocyclic Chemistry, 5th ed. Chichester: Blackwell Publishing, 2010.

27. Eicher T., Hauptmann S. The Chemistry of Heterocycles. Structure, Reactions, Syntheses, and Applications, 2nd ed. Weinheim: Wiley-VCH, 2003.

28. Chupakhin O.N., Charushin V.N., van der Plas H.C. Nucleophilic Aromatic Substitution of Hydrogen. New York, San Diego: Academic Press, 1994.

29. Charushin V.N., Chupakhin O.N. Mendeleev Commun. 2007, 17, 249-254.
http://dx.doi.org/10.1016/j.mencom.2007.09.001

30. Charushin V.N., Chupakhin O.N. Pure Appl. Chem. 2004, 76, 1621-1631.
http://dx.doi.org/10.1351/pac200476091621

31. Brasse M., Ellman J. A., Bergman R. G. Chem. Commun. 2011, 47, 5019-5021.
http://dx.doi.org/10.1039/c1cc10507h

32. Mąkosza M. Chem. Soc. Rev. 2010, 39, 2855-2868.
http://dx.doi.org/10.1039/b822559c

33. Mąkosza M. Synthesis 2011, 15, 2341-2356.
http://dx.doi.org/10.1055/s-0030-1260668

34. Beresnev D.G., Itsikson N.A., Chupakhin O.N., Charushin V.N., Kodess M.I., Butakov A.I., Rusinov G.L., Morzherin Y.Yu., Konovalov A.I., Antipin I.S. J. Org. Chem. 2006, 71, 8272-8275.
http://dx.doi.org/10.1021/jo061069d

35. Sheldon R.A., Arends I., Hanefeld U. Green Chemistry and Catalysis. Weinheim: John Wiley & Sons, 2007.
http://dx.doi.org/10.1002/9783527611003

36. Trost B.M. Science 1991, 254, 1471-1477.
http://dx.doi.org/10.1126/science.1962206

37. Gutsche C.D., Dhawan B., Levine J.A., No K.H., Bauer L.J. Tetrahedron 1983, 39, 409-426.
http://dx.doi.org/10.1016/S0040-4020(01)88541-0

38. Saraswathi T.V., Srinivasan V.R. Tetrahedron 1977, 33, 1043-1051.
http://dx.doi.org/10.1016/0040-4020(77)80223-8

39. Utepova I.A., Musikhina A.A., Chupakhin O.N., Slepukhin P.A. Organometallics 2011, 30, 3047-3053.
http://dx.doi.org/10.1021/om200159f

40. Senge M.O., Bischoff I. Eur. J. Org. Chem. 2001, 1735-1751.
http://dx.doi.org/10.1002/1099-0690(200105)2001:9<1735::AID-EJOC1735>3.0.CO;2-6

41. Chupakhin O.N., Utepova I.A., Kovalev I.S., Rusinov V.L., Starikova Z.A. Eur. J. Org. Chem. 2007, 857-862.
http://dx.doi.org/10.1002/ejoc.200600821

42. Varaksin M.V., Utepova I.A., Chupakhin O.N. Chem. Heterocycl. Compd. 2012, 48, 1213-1219.
http://dx.doi.org/10.1007/s10593-012-1124-x

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Synthesis of New meso-Substituted Heterocyclic Calix[4]arenes via SN H Approach

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