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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 41, 2011 - Issue 5
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Original Articles

Synthesis of Resorcinarene Derivatives via the Catalyzed Mannich Reaction, Part 3: Glycol Derivatives of Resorcinarene

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Pages 670-676 | Received 05 Nov 2009, Published online: 31 Jan 2011

REFERENCES

  • Łęska , B. ; Gierczyk , B. ; Eitner , K. ; Rybachenko , V. I.; Schroeder G. Studies of silicon podand solvents . Supramol. Chem. 2004 , 16 , 303 – 310 .
  • Delgado , M. ; Gustowski , D. A. ; Yoo , H. K. ; Gatto , V. J. ; Gokel , G. W. ; Echegoyen , L. Contrasting one- and two-cation binding behavior in syn and anti-anthraquinone bibracchial podand (BiP) mono- and dianions assessed by cyclic voltammetry and electron paramagnetic resonance spectroscopy . J. Am. Chem. Soc. 1988 , 110 , 119 – 124 .
  • Arunkumar , E. ; Chithra , P. ; Ajayaghosh , A. A controlled supramolecular approach toward cation-specific chemosensors: Alkaline earth metal ion-driven exciton signaling in squaraine tethered podands . J. Am. Chem. Soc. 2004 , 126 , 6590 – 6598 .
  • Gokel , G. W. ; Murillo , O. In Comprehensive Supramolecular Chemistry , Vol. 1 ; Pergamon Press : New York , 1996 .
  • Gokel , G. W. In Large Ring Molecules ; J. A. Semlyen (Ed.); John Wiley : New York , 1996 .
  • Jeong , K.-S. ; Cho , Y. L. ; Pyun , S. Y. Podand ionophores capable of forming cation-binding cavities through intermolecular interactions between the terminal groups . Tetrahedron Lett. 1995 , 36 , 2827 – 2830 .
  • Aspinall , H. C. ; Greeves , N. ; McIver , E. G. Modular chiral polyether podands and their lanthanide complexes . Tetrahedron 2003 , 59 , 10453 – 10463 .
  • Ziessel , R. ; Hissler , M. ; Ulrich , G. Synthesis of polydendate acyclic and macrocyclic polyamine ligands bearing 2,2′-bipyridine or 2,2′-bipyridine N,N′-dioxide moieties . Synthesis 1998 , 1339 – 1346 .
  • Deshayes , K. ; Broene , R. D. ; Chao , I. ; Knobler , C. B. ; Diederich , F. Synthesis of the helicopodands: Novel shapes for chiral clefts . J. Org. Chem. 1991 , 56 , 6787 – 6795 .
  • Turner , D. R. ; Paterson , M. J. ; Steed , J. W. A conformationally flexible, urea-based tripodal anion receptor: Solid-state, solution, and theoretical studies . J. Org. Chem. 2006 , 71 , 1598 – 1608 .
  • Gokel , G. W. ; Leevy , W. M. ; Weber , M. E. Crown ethers: Sensors for ions and molecular scaffolds for materials and biological models. Chem. Rev. 2004, 104, 2723–2750.
  • Menuel , S. ; Joly , J.-P. ; Courcot , B. ; Elysée , J. ; Ghermani , N.-E. ; Marsura , A. Synthesis and inclusion ability of a bis-β-cyclodextrin pseudo-cryptand towards busulfan anticancer agent . Tetrahedron 2007 , 63 , 1706 – 1714 .
  • Wagner , M. ; Engrand , P. ; Regnouf-de-Vains , J.-B. ; Marsura , A. Heptakis-6-(5-methylene-ureido-5′-methyl-2,2′-bithiazolyl)-cyclomaltoheptaose as a new fluorescent polydentate ligand . Tetrahedron Lett. 2001 , 42 , 5207 – 5209 .
  • Ben Salem , A. ; Regnouf-de-Vains , J.-B. Towards a new family of calixarene-based podands incorporating quinolone arms: An example using nalidixic acid . Tetrahedron Lett. 2003 , 44 , 6769 – 6771 .
  • Ulrich , G. ; Ziessel , R. ; Manet , L. ; Guardigli , M. ; Sabbatini , N. ; Fraternali , F. ; Wipff , G. Calix-4-arene podands and barrelands incorporating 2,2′-bipyridine moieties and their lanthanide complexes: Luminescence properties . Chem. Eur. J. 1997 , 3 , 1815 – 1822 .
  • Casnati , A. ; Sansone , F. ; Ungaro , R. Peptido- and glycocalixarenes: Playing with hydrogen bonds around hydrophobic cavities . Acc. Chem. Res. 2003 , 36 , 246 – 254 .
  • Casnati , A. ; Ungaro , R. In Calixarenes in Action ; L. Mandolini , R. Ungaro (Eds.); Imperial College Press : London , 2000 .
  • Urbaniak , M. ; Iwanek , W. Synthesis of alkoxymethyl derivatives of resorcinarene via the Mannich reaction catalysed with iminodiacetic acid . Tetrahedron 2006 , 62 , 1508 – 1511 .
  • Urbaniak , M. ; Iwanek , W. Synthesis of resorcinarene derivatives by the catalyzed Mannich reaction, part 2: Resorcinarene derivatives with unsaturated bonds . Synth. Commun. 2008 , 38 , 4345 – 4351 .
  • For reviews of resorcinarene derivatives synthesized via a Mannich reaction, see (a) Tramontini , M. Advances in the chemistry of Mannich bases . Synthesis 1973 , 703 – 775 ; (b) Timmerman , P. ; Verboom , W. ; Reinhoudt , D. N. Resorcinarenes . Tetrahedron 1996 , 52 , 2663 – 2704 ; (c) Airola , K. ; Böhmer , V. ; Paulus , E. F. ; Rissanen , K. ; Schmidt , C. ; Thondorf , I. ; Vogt , W. Selective derivatisation of resorcarenes, 1: The regioselective formation of tetra-benzoxazine derivatives . Tetrahedron 1997 , 53 , 10709 – 10724 ; (d) Schmidt , C. ; Straub , T. ; Falàbu , D. ; Paulus , E. F. ; Wegelius , E. ; Kolehmainen , E. ; Böhmer , V. ; Rissanen , K. ; Vogt , W. Selective derivatisation of resorcarenes, 6: Mannich reactions with amino alcohols . Eur. J. Org. Chem. 2000 , 3937 – 3944 ; (e) El Gihani , M. T. ; Heaney , H. ; Slawin , A. M. Z. Highly diastereoselective functionalisation of calix[4]resorcinarene derivatives and acid-catalysed epimerisation reactions . Tetrahedron Lett. 1995 , 36 , 4905 – 4908 ; (f) Iwanek , W. ; Wolff , C. ; Mattay , J. Chiral calixarenes derived from resorcinol II: Functionalization by Mannich reaction with α-aminoalcohols . Tetrahedron Lett. 1995 , 36 , 8969 – 8972 ; (g) Luostarinen , M. ; Shivanyuk , A. ; Rissanen , K. Partial aminomethylation of resorcarenes . Org. Lett. 2001 , 3 ( 26 ), 4141 – 4144 ; (h) Arnott , G. ; Heaney , H. ; Hunter , R. ; Page , P. C. B. Synthesis of the first chiral, functionalised-bridged resorcinarenes in asymmetric catalysis: Evidence for intracavity asymmetric catalysis . Eur. J. Org. Chem. 2004 , 5126 – 5134 .

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