Synthesis of p-tert-Butyldihomooxacalix[4]arene Mono-substituted Dithiocarbonylhydrazones and Dithiosemicarbazones

References

• (a) C.D. Gutsche, R. Muthukrishnan, and K. H. No, “Calixarenes II. The isolation and characterization of the calix[4]arene and the bishomooxacalix[4]arene from a p-t-butylphenol-formaldehyde condensation,” Tetrahedron Letters 24 (1979): 2213–16;
   Google Scholar
  (b) M.A. Mckervey, E.M. Seward, G. Ferguson, B. Ruhl, and S. J. Harris, “Synthesis, X-ray crystal structures, and cation transfer properties of alkyl calixaryl acetates, a new series of molecular receptors,” Journal of the Chemical Society, Chemical Communications 5 (1985): 388–90.
   Google Scholar
• (a) C.D. Gutsche, B. Dhawan, K.H. No, and R. Muthukrishnan, “Calixarenes. 4. The synthesis, characterization, and properties of the calixarenes from p-tert-butylphenol,” Journal of American Chemical Society 103 (1981): 3782–9;
   Web of Science ®Google Scholar
  (b) B. Dhawan and C.D. Gutsche, “Calixarenes. 10. Oxacalixarenes,” Journal of Organic Chemistry 48 (1983): 1536–39;
   Web of Science ®Google Scholar
  (c) C.D. Gutsche, and L.J. Bauer, “Calixarenes. 13. The conformational properties of calix[4]arenes, calix[6]arenes, calix[8]arenes, and oxacalixarenes,” Journal of American Chemical Society 107 (1985): 6052–59.
   Web of Science ®Google Scholar
• (a) B. Masci, in Calixarenes, edited by Z. Asfari, V. Böhmer, J. Harrowfield, and J. Vicens, (Dordrecht: Kluwer Academic, 2001); 235–49;
   Google Scholar
  (b) P.M. Marcos, in Calixarenes and Beyond, edited by P. Neri, J.L. Sesseler, and M.-X. Wang (Switzerland: Springer International Publishing, 2016); 445–66.
   Google Scholar
• (a) C. Bavoux, F. Vocanson, M. Perrin, and R. Lamartine, “New synthesis and complexing properties of p-tert-butyldihomooxacalix[4]arene. Structure of its 1:2 complex with tetrahydrofuran,” Journal of Inclusion Phenomena and Molecular Recognition in Chemistry 22 (1995): 119–30;
   Web of Science ®Google Scholar
  (b) P.M. Marcos, J. Ascenso, R. Lamartine, and J.C. Pereira, “Synthesis and NMR conformational studies of p-tert-butyldihomooxacalix[4]-arene derivatives,” Supramolecular Chemistry 6 (1996): 303–06;
   Web of Science ®Google Scholar
  (c) P.M. Marcos, J.R. Ascenso, R. Lamartine, and J.L.C. Pereira, “Conformational studies of tetraalkylated dihomooxacalix[4]arenes,” Tetrahedron 53 (1997): 11791–802;
   Web of Science ®Google Scholar
  (d) B. Masci, M. Finelli, and M. Varrone, “Fine tuning of the cavity size in calixarene-like cyclophanes: A complete series of homooxacalix[4]arene ligands for quaternary ammonium ions,” Chemistry: A European Journal 4 (1998): 2018–30.
   Web of Science ®Google Scholar
• (a) P.M. Marcos, J.R. Ascenso, R. Lamartine, and J.L.C. Pereira, “Synthesis and conformational characteristics of inherently chiral monoalkyl ethers of p-tert-butyldihomooxacalix[4]arene,” Journal of Organic Chemistry 63 (1998): 69–74;
   PubMed Web of Science ®Google Scholar
  (b) M. Perrin, S. Lecocq, P.M. Marcos, and J.L.C. Pereira, “Substituent effects in dihomooxacalix[4]arenes: Conformations and crystal structures of dihomooxacalix[4]arenes tetrasubstituted at the OH groups,” Supramolecular Chemistry 9 (1998): 137–41;
   Web of Science ®Google Scholar
  (c) M.A. Santos, P.M. Marcos, and J.L.C. Pereirac, “Conformational analysis of a tetrabenzylated dihomooxacalix[4]arene. A theoretical study,” Journal of Molecular Structure (Theochem) 463 (1999): 21–26;
   Web of Science ®Google Scholar
  (d) K.I. Tomita, K. Suzuki, H. Ohishi, and I. Nakanishi, “Molecular structure and mutual recognition between host and guest molecules found in the crystal structures of oxacalix[4]arenes complexed with xylene isomers,” Journal of Inclusion Phenomena and Molecular Recognition in Chemistry 37 (2000): 341–57.
   Google Scholar
• (a) B. Masci, “New parent homooxacalixarenes through thermal dehydration of a bishydroxymethylated triphenol,” Journal of Organic Chemistry 66 (2001): 1497–99;
   PubMed Web of Science ®Google Scholar
  (b) B. Masci, S. L., Mortera, D. Persiani, and P. Thuéry, “Methyl ether derivatives of p-tert-butyl[3.1.3.1]homooxacalixarene. Formation, structure, and complexes with quaternary ammonium ions,” Journal of Organic Chemistry 71 (2006): 504–11;
   PubMed Web of Science ®Google Scholar
  (c) R. Lavendomme, P.J. Cragg, P.M. Marcos, M. Luhmer, and I. Jabin, “ Synthesis of (Homooxa)calixarene–monoquinones through the “All-but-One” methodology,” Organic Letters 17 (2015): 5690–93.
   PubMed Web of Science ®Google Scholar
• (a) P.M. Marcos, J.R. Ascenso, M.A.P. Segurado, and J.L.C. Pereira, “Alkali and alkaline-earth metal cation complexation and transport properties by tetraphenyl ketone of p-tert-butyldihomooxacalix[4]arene,” Journal of Physical Organic Chemistry 12 (1999): 695–702;
   Web of Science ®Google Scholar
  (b) P.M. Marcos, J.R. Ascenso, M.A.P. Segurado, and J.L.C. Pereira, “Synthesis, NMR conformational analysis, complexation and transport studies of an inherently chiral dihomooxacalix[4]arene triester,” Tetrahedron 57 (2001): 6977–84;
   Web of Science ®Google Scholar
  (c) P.M. Marcos, J.R. Ascenso, and J.L.C. Pereira, “Synthesis and NMR conformational studies of p-tert-butyldihomooxacalix[4]arene derivatives bearing pyridyl pendant groups at the lower rim,” European Journal of Organic Chemistry 17 (2002): 3034–41.
   Google Scholar
• (a) P.M. Marcos, J.R. Ascenso, M.A.P. Segurado, and J.L.C. Pereira, “p-tert-Butyldihomooxacalix[4]arene/p-tert-Butylcalix[4]arene: Transition and heavy metal cation extraction and transport studies by ketone and ester derivatives,” Journal of Inclusion Phenomena and Molecular Recognition in Chemistry 42 (2002): 281–88;
   Google Scholar
  (b) P.M. Marcos and J. R. Ascenso, “Synthesis, NMR characterization and ion binding properties of 1,3-bridged p-tert-butyldihomooxacalix[4]crown-6 bearing pyridyl pendant groups,” Tetrahedron 62 (2006): 3081–88;
   Web of Science ®Google Scholar
  (c) P.M. Marcos, S. Félix, J.R. Ascenso, M.A.P. Segurado, B. Mellah, and R. Abidi, “Complexation and transport of alkali and alkaline earth metal cations by p-tert-butyldihomooxacalix[4]arene tetraketone derivatives,” Supramolecular Chemistry 18 (2006): 285–97;
   Web of Science ®Google Scholar
  (d) P.M. Marcos, S. Félix, J.R. Ascenso, M.A. Segurado, P.P. Thuéry, B. Mellah, … F. Arnaud-Neu, “Complexation and transport of transition and heavy metal cations by p-tert-butyldihomooxacalix[4]arene tetraketones and X-ray crystal structure of the tert-butyl ketone derivative,” New Journal of Chemistry 31 (2007): 2111–19.
   Web of Science ®Google Scholar
• (a) P.M. Marcos, F.A. Teixeira, M.A. Segurado, J.R. Ascenso, R.J. Bernardino, G. Brancatelli, and S. Geremia, “Synthesis and anion binding properties of new dihomooxacalix[4]arene diurea and dithiourea receptors,” Tetrahedron 70 (2014): 6497–505;
   Web of Science ®Google Scholar
  (b) P.M. Marcos, F.A. Teixeira, M.A.P. Segurado, J.R. Ascenso, R.J. Bernardino, S. Michel, and V. Hubscher-Bruder, “ Bidentate urea derivatives of p-tert-butyldihomooxacalix[4]arene: Neutral receptors for anion complexation,” Journal of Organic Chemistry 79 (2014): 742–51.
   PubMed Web of Science ®Google Scholar
• (a) F.A. Teixeira, P.M. Marcos, J.R. Ascenso, G. Brancatelli, N. Hickey, and S. Geremia, “Selective binding of spherical and linear anions by tetraphenyl(thio)urea-based dihomooxacalix[4]arene receptors,” Journal of Organic Chemistry 82 (2017), 11383–90;
   PubMed Web of Science ®Google Scholar
  (b) A.S. Augusto, A.S. Miranda, J.R. Ascenso, M.Q. Miranda, V. Felix, G. Brancatelli, … P.M. Marcos, “Anion recognition by partial cone dihomooxacalix[4]arene-based receptors bearing urea groups: Remarkable affinity for benzoate ion,” European Journal of Organic Chemistry 41 (2018): 5657–67.
   Google Scholar
• (a) Y. Liu, J. Sun, and C.G. Yan, “Synthesis and crystal structures of p-tert-butyldihomooxacalix[4]arene mono-Schiff bases,” Journal of Inclusion Phenomena and Molecular Recognition in Chemistry 87 (2017): 157–66;
   Google Scholar
  (b) Y. Liu, L.L. Zhao, J. Sun, C.G. Yan, “Convenient synthesis and coordination properties of p-tert-butyldihomooxacalix[4]arene mono-Schiff Bases,” Polycyclic Aromatic Compound (2018). doi.https://org/10.1080/10406638.2018.1469520;
   Web of Science ®Google Scholar
  (c) L. An, J.W. Wang, C. Wang, S.S. Zhou, J. Sun, and C.G. Yan, “2,3-Ethylene-bridged dihomooxacalix[4]arenes: Synthesis, X-ray crystal structures and highly selective binding properties with anions,” New Journal of Chemistry 42 (2018): 10689–96.
   Google Scholar
• (a) X.Y. Chen, F.J. Femia, J.W. Babich, and J. Zubieta, “Exploring oxorhenium "3 + 1" mixed-ligand complexes carrying the S-benzyl-3-[(2-hydroxyphenyl)methylene]dithiocarbazate [ONS]/monothiol [S] donor set: synthesis and characterization,” Inorganic Chimica Acta 307 (2000): 154–9;
   PubMed Web of Science ®Google Scholar
  (b) S. M. Abdel-Gawad, M. S. Elgendy, and Abdelhamid, O. A., “Reactions with hydrazonoyl halides. 46. Synthesis of some new 2,3-dihydro-1,3,4-thiadiazoles and triazolino[4,3-a]pyrimidines as antimicrobial agents,” Journal of Sulfur Chemistry 26 (2005), 21–31;
   Google Scholar
  (c) D.R. Wang, M. Ebel, C. Schulzke, C. Gruning, S.K.S. Hazari, and D. Rehder, “Vanadium(IV and V) complexes containing SNO (dithiocarbonylhydrazone; thiosemicarbazone) donor sets,” European Journal of Inorganic Chemistry 4 (2001): 935–42;
   Google Scholar
  (d) T. Sedaghat, and A. Zamani, “Coordination chemistry and spectroscopic properties of some diorganotin(IV) complexes with S-donor Schiff base ligands,” Phosphorus, Sulfur and Silicon and the Related Elements, 186 (2011), 606–12.
   Web of Science ®Google Scholar
• (a) J.H. Zhu, X.D. Zheng, G.Z. Guo, Y.Q. Zhang, and B.W. Wu, “Microwave-assisted synthesis of asymmetrical 1,5-disubstituted carbonohydrazide and crystal structure,” Chinese Journal of Organic Chemistry 35 (2015): 1975–80;
   Web of Science ®Google Scholar
  (b) S.M. Annigeri, M.P. Sathisha, and V.K. Revankar, “Synthesis and spectral characterization of some binuclear complexes designed from N4O and N2O3 donor Schiff-base ligands of 2,6-diformyl-4-methylphenol,” Journal of Coordination Chemistry 61 (2008): 4011–24.
   Web of Science ®Google Scholar
• (a) T. Stringer, D.T. Hendricks, H. Guzgay, and G.S. Smith, “Synthesis and characterization of multimeric salicylaldimine thiosemicarbazones and their Pd(II) and Pt(II) complexes,” Polyhedron 31 (2012): 486–93;
   Web of Science ®Google Scholar
  (b) T. Stringer, D. Taylor, C. de Kock, H. Guzgay, A. Au, S.H. An, … G.S. Smith, “Synthesis, characterization, antiparasitic and cytotoxic evaluation of thioureas conjugated to polyamine scaffolds,” European Journal of Medical Chemistry 69 (2013): 90–8.
   PubMed Web of Science ®Google Scholar