Synthesis 2013; 45(24): 3341-3348
DOI: 10.1055/s-0033-1338518
practical synthetic procedures
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Tripodal and Hexapodal Pyrazole- and Benzimidazole-Bearing Compounds

Niklas Koch
Institut für Organische Chemie, Technische Universität Bergakademie Freiberg, Leipziger Strasse 29, 09596 Freiberg, Germany   Fax: +49(3731)393170   Email: monika.mazik@chemie.tu-freiberg.de
,
Monika Mazik*
Institut für Organische Chemie, Technische Universität Bergakademie Freiberg, Leipziger Strasse 29, 09596 Freiberg, Germany   Fax: +49(3731)393170   Email: monika.mazik@chemie.tu-freiberg.de
› Author Affiliations
Further Information

Publication History

Received: 30 April 2013

Accepted after revision: 11 July 2013

Publication Date:
29 August 2013 (online)


Abstract

The syntheses of eight new tripodal and hexapodal benzimidazole- and pyrazole-bearing compounds, which are all potentially applicable for use as artificial receptors, are described. The prepared compounds contain either bromo-substituted heteroaromatic rings, able to participate in halogen-bonding interactions, or their analogues lacking the bromo substituents. Furthermore, the preparation of a new trisbenzimidazolium cage is included in this work. All used practical synthetic procedures are facilely accomplishable and provide the products in good to excellent yields. In addition, slightly modified, simplified synthetic procedures for five known tripodal compounds, which lead to better yields than those previously reported, are also detailed.

Supporting Information

 
  • References

    • 1a Kuswandi B, , Nuriman Verboom W, Reinhoudt DN. Sensors 2006; 6: 978
    • 1b Hennrich G, Anslyn EV. Chem. Eur. J. 2002; 8: 2219
    • 1c Mazik M. Chem. Soc. Rev. 2009; 38: 935
    • 1d Mazik M. RSC Adv. 2012; 2: 2630
    • 2a Chin J, Walsdorff C, Stranix B, Oh J, Chung HJ, Park S.-M, Kim K. Angew. Chem. Int. Ed. 1999; 38: 2756
    • 2b Chin J, Oh SY, Park SH, Walsdorff C, Stranix B, Ghoussoub A, Lee SJ, Chung HJ, Park S.-M, Kim K. J. Am. Chem. Soc. 2002; 124: 5374
    • 2c Lee DY, Singh N, Kim MJ, Jang DO. Org. Lett. 2011; 13: 3024
    • 2d Singh N, Jang DO. Org. Lett. 2007; 9: 1991
    • 2e Joo TY, Singh N, Lee GW, Jang DO. Tetrahedron Lett. 2007; 48: 8846
    • 2f Gale PA, Hiscock JR, Lalaoui N, Light ME, Wells NJ, Wenzel M. Org. Biomol. Chem. 2012; 10: 5909

      For selected reviews, see:
    • 3a Gale PA. Chem. Soc. Rev. 2010; 39: 3746
    • 3b Gale PA. Coord. Chem. Rev. 2006; 250: 2917
    • 3c Späth A, König B. Beilstein J. Org. Chem. 2010; 6: No. 32
  • 4 For a description of poly(pyrazol-1-ylmethyl)benzenes as multidentate chelating ligands, see: Hartshorn CM, Steel PJ. Aust. J. Chem. 1995; 48: 1587
    • 5a Sonnenberg C, Hartmann A, Mazik M. Nat. Prod. Commun. 2012; 7: 321
    • 5b Mazik M, Cavga H. J. Org. Chem. 2007; 72: 831
  • 6 Arunachalam M, Ahamed BN, Ghosh P. Org. Lett. 2010; 12: 2742
  • 7 Hartshorn CM, Steel PJ. Chem. Commun. 1997; 541
  • 8 Castellano RK, Li Y, Homan EA, Lampkins AJ, Marín IV, Abboud KA. Eur. J. Org. Chem. 2012; 4483
    • 9a Li H, Homan EA, Lampkins AJ, Ghiviriga I, Castellano RK. Org. Lett. 2005; 7: 443
    • 9b Koch N, Seichter W, Mazik M. Acta Crystallogr., Sect. E: Struct. Rep. Online 2013; 69: o679
  • 10 Wallace KJ, Hanes R, Anslyn E, Morey J, Kilway KV, Siegel J. Synthesis 2005; 2080
  • 11 Zavada J, Pankova M, Holy P, Tichy M. Synthesis 1994; 1132
    • 12a Yuan Y, Jiang Z.-J, Yan J.-M, Gao G, Chan AS. C, Xie R.-G. Synth. Commun. 2000; 30: 4555
    • 12b Yuan Y, Gao G, Jiang Z.-L, You J.-S, Zhou Z.-Y, Yuan D.-Q, Xie R.-G. Tetrahedron 2002; 58: 8993
    • 12c Xu Z, Singh NJ, Kim SK, Spring DR, Kim KS, Yoon J. Chem. Eur. J. 2011; 17: 1163
  • 13 Amendola V, Bergamaschi G, Boiocchi M, Fabbrizzi L, Fusco N. Dalton Trans. 2011; 40: 8367