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Macrostructures Derived from Dichloropyrimidines

Autorzy
Identyfikatory
Warianty tytułu
Konferencja
Symposium "From Molecular Recognition to Molecular Devices", September 20-22, Gdańsk, Poland
Języki publikacji
EN
Abstrakty
EN
This account provides a summary of our research during the last 10 years (1997-2007) on the synthetic exploration of various macro structures derived from dichloropyrimidine building blocks. Pyrimidine precursors have been used for the construction of functional porphyrinoids, (porphyrin) dendrimers, and heteracalix[n]arenes. meso- Pyri midinyl - porphyrinoids have been synthesized starting from 4,6-dichloropyrimidine- 5-carbaldehydes, and the result ing oligopyrrolic macrocycles were functionalized and superstructured in several different fashions. Pyrimidine-based (porphyrin) dendrimers have been constructed via a convergent strategy using a pyrimidine AB2-monomer. The dendritic surface was equipped with different moieties, al lowing their exploration as dendritic oxidation catalysts. Finally, oxacalix[m]arene[m]pyrimidines (m = 2-6), a novel class of heteracalix(heter)arenes, have recently been prepared via nucleophilic aromatic substitution reactions on 4,6-dihalopyrimidines. In these cyclooligomeric species, the pyrimidine component al lows the introduction of avariety of functional moieties on the calixarene scaf fold.
Słowa kluczowe
Rocznik
Strony
1146--1160
Opis fizyczny
Bibliogr. 29 poz., rys.
Twórcy
autor
autor
  • Molecular Design and Synthesis, Department of Chemistry, Katholieke Universiteit Leuven, Celestijnenlaan 200F, 3001 Leuven, Belgium Fax: +32 16 327990; Tel.: +32 16 327439, wim.dehaen@chem.kuleuven.be
Bibliografia
  • 1. von Angerer S., in: Science of Synthesis, Yamamoto Y., Ed., Georg Thieme Verlag, Stuttgart 2004, vol. 16, p. 379.
  • 2. Ruben M., Rojo J., Romero-Salguero F.J., Uppadine L.H. and Lenn J.-M., Angew. Chem., Int. Ed., 43,3644 (2004).
  • 3. (a) Neys P.E.F., Yankelecom I.F.J., L'abbe M., Parton R.F., Ceulemans E., Dehaen W., L'abbe G. and Jacobs P.A., J. Mol. Catal A: Chem., 134,209 (l998); (b) van Laar F.M.P.R., Holsteyns F., Vankelecom I.F.J., Smeets S., Dehaen W. and Jacobs P.A., J. Photochem. Photobiol. A: Chem., 144, 141 (2001).
  • 4. Motmans F., Ceulemans E., Smeets S. and Dehaen W., Tetrahedron Lett., 40, 7545 (1999).
  • 5. Smeets S., Asokan C.Y, Motmans F. and Dehaen W., J. Org. Chem., 65, 5882 (2000).
  • 6. Maes W. and Dehaen W., Synlett, 79 (2003).
  • 7. Sessler J.L. and Weghorn S.J., Expanded, Contracted and Isomeric Porphyrins, Elsevier, Oxford 1997.
  • 8. Synthetic corrole chemistry up to 1999: Paolesse R., in: The Porphyrin Handbook, Kadish K.M., Smith K.M. and Guilard R., Eds., Academic Press, San Diego 2000, vol. 2, chapter 11, p. 201.
  • 9. (a) Yogel E., Will S., Shulze-Tilling A., Neumann L., Lex J., Bili E., Trautwein A.X. and Wieghardt A., Angew. Chem., Int. Ed., 33,731 (1994); (b) Gross Z., GaliliN. and Saltsman l., Angew. Chem., Int. Ed., 38, 1427 (1999); (c) Paolesse R., Jaquinod L., Nurco D.J., Mini S., Sagone F., Boschi T. and Smith K.M., Chem. Commun., 1307 (1999).
  • 10. Nardis S., Monti D. and Paolesse R., Mini-Rev. Org. Chem., 2, 355 (2005).
  • 11. Aviv I. and Gross Z., Chem. Commun., 1987 (2007).
  • 12. Asokan C.Y, Smeets S. and Dehaen W., Tetrahedron Lett., 42, 4483 (2001).
  • 13. Maes W., Ngo T.H., Vanderhaeghen J. and Dehaen W., Org. Lett., 9, 3165 (2007).
  • 14. (a) FurutaH., MaedaH. and Osuka A., Chem. Commun., 1795 (2002); (b) Shimizu S., Shin J.-Y, Furuta H.,Ismael R. and Osuka A., Angew. Chem., Int. Ed., 42, 78 (2003); (c) Hata H., Shinokubo H. and Osuka A., Angew. Chem., Int. Ed., 44, 932 (2005).
  • 15. Maes W., Yanderhaeghen J. and Dehaen W., Chem. Commun., 2612 (2005).
  • 16. (a) Newkome G.R., Moorefield C.N. and Vögtle F., Dendrimers and Dendrons: Concepts, Syntheses,Applications, Wiley-VCH, Weinheim 2001; (b) Recent Developments in Dendrimer Chemistry,Tetrahedron Symposium-in-Print 96, Smith D.K., Ed., Tetrahedron, 59,3787 (2003); (c) Special Issue:Dendrimers and Dendritic Polymers, TomaliaD.A. and Fröchet J.M.J., Eds., Prog. Polym. Sci., 30,217 (2005).
  • 17. Maes W. and Dehaen W., Dendrimers containing N-, O-Heterocycles, in Modern Approaches to the Synthesis of O- and N-Heterocycles, Kaufinan T.S. and Larghi L.S., Eds., Research Signpost, 2007, vol. 2, p. 309.
  • 18. Verheyde B. and Dehaen W., J. Org. Chem., 66, 4062 (2001).
  • 19. Verheyde B., Maes W. and Dehaen W., Mater. Sci. Eng. C, 18, 243 (2001).
  • 20. Maes W., Amabilino D.B. and Dehaen W., Tetrahedron, 59, 3937 (2003).
  • 21. Maes W., Verstappen B. and Dehaen W., Tetrahedron, 62, 2677 (2006).
  • 22. Chavan S., Maes W., Wahlen J., Jacobs P., De Vos D. and Dehaen W., Catal. Commun., 6,241 (2005).
  • 23. Chavan S.A., Maes W., Gevers L.E.M., Wahlen J., Vankelecom I.F.J., Jacobs P.A., Dehaen W. and De Vos D.E., Chem. Eur. J., 11, 6754 (2005).
  • 24. Maes W, Vanderhaeghen J., Smeets S., Asokan C.Y, Van Renterghem L.M., Du Prez F.E., Smet M. and Dehaen W, J. Org. Chem., 71, 2987 (2006).
  • 25. (a) Gutsche C.D., Calixarenes Revisited, Royal Society of Chemistry, Cambridge 1998; (b) Asfari Z.,Böhmer Y, Harrowfield J. and Vicens J., Eds., Calixarenes 2001, Kluwer Academic Publishers, Dordrecht 2001.
  • 26. (a) Lhotak R, Eur. J. Org. Chem., 1675 (2004); (b) Morohashi N., Narumi R, Iki N., Hattori T. and Miyano S., Chem. Rev., 106, 5291 (2006).
  • 27. (a) Wang M. and Yang H., J. Am. Chem. Soc., 126,15412 (2004); (b) Katz J.L., Feldman M.B. and Conry R.R., Org. Lett., 7, 91 (2005).
  • 28. Maes W., Van Rossom W., Van Hecke K., Van Meervelt L. and Dehaen W., Org. Lett., 8,4161 (2006).
  • 29. Van Rossom W., Maes W., Kishore L., Ovaere M., Van Meervelt L. and Dehaen W., Org. Lett., 10, 585 2008).
Typ dokumentu
Bibliografia
Identyfikator YADDA
bwmeta1.element.baztech-article-BUJ6-0024-0125
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