Download PDF
Synthesis 2009(15): 2557-2560  
DOI: 10.1055/s-0029-1217398
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of a Novel Class of Azacrown Macrocycles and Lariat Crown Ethers Containing Two 1,2,4-Triazole Rings as Subunits

Naser Foroughifar*, Akbar Mobinikhaledi, Sattar Ebrahimi
Department of Chemistry, Faculty of Sciences, Arak University, Arak 38156-879, Iran
Fax: +98(861)4173406; e-Mail: n_foroughifar@yahoo.com;
Further Information

Publication History

Received 26 March 2009
Publication Date:
22 June 2009 (online)

    Permissions and Reprints All articles of this category

Abstract

Azacrown macrocycles were prepared in 70-76% yield by the condensation reaction of 1,2-, 1,3-, and 1,4-bis(4-amino-5-mercapto-4H-1,2,4-triazol-3-yl)alkanes with bisaldehydes in acetic acid under reflux. Reaction of two of these azacrown macrocycles with iodomethane and benzyl chloride furnished exclusively the target lariat macrocycles in good yields.

Key words

azacrown macrocycles - 1,2,4-triazole - thiols - bistri­azoles - lariat crown ethers

    References

  • 1 Pedersen CJ. J. Am. Chem. Soc.  1967,  89:  7017 
    CrossrefGoogle Scholar
  • 2 Pedersen CJ. J. Am. Chem. Soc.  1967,  89:  2495 
    CrossrefGoogle Scholar
  • 3 Gokel GW. Crown Ethers and Cryptands (Monographs in Supramolecular Chemistry)   The Royal Society of Chemistry; Cambridge: 1991. 3
    Google Scholar
  • 4 Richard ED. Milton DG. J. Am. Chem. Soc.  1976,  98:  762 
    CrossrefGoogle Scholar
  • 5 Newkome GR. Sauer JD. Rober JM. Hager DC. Chem. Rev.  1977,  77:  513 
    CrossrefGoogle Scholar
  • 6a Gokel GW. Federes MF. In Comprehensive Heterocyclic Chemistry   Vol. 9:  Elsevier; Oxford: 1996.  p.863 
    Google Scholar
  • 6b Weber E. Kontakte (Darmstadt)  1983,  38 
    Google Scholar
  • 7a Bradshaw JS. J. Inclusion Phenom. Macrocyclic Chem.  1997,  29:  221 
    Google Scholar
  • 7b Weber E. Kohler HJ. Reuter HJ. J. Org. Chem.  1991,  56:  1236 
    Google Scholar
  • 8a Bradshaw JS. Huszthy P. McDaniel CW. Zhu CY. Dalley NK. Izatt RM. Lifson S. J. Org. Chem.  1990,  55:  3129 
    Google Scholar
  • 8b Bradshaw JS. Thompson PK. Izatt RM. J. Heterocycl. Chem.  1984,  21:  897 
    Google Scholar
  • 9a Collier CP. Mattersteig G. Wong EW. Luo Y. Beverly K. Sampaio J. Raymo FM. Stoddart JF. Heath JR. Science (Washington, D.C.)  2000,  289:  1172 
    Google Scholar
  • 9b Jefferson EA. Swayze EE. Osgood SA. Miyaji A. Risen LM. Blyn LB. Bioorg. Med. Chem. Lett.  2003,  13:  1635 
    Google Scholar
  • 9c Jian L. Tington L. Yongmei W. Eur. J. Med. Chem.  2008,  43:  19 
    Google Scholar
  • 9d Huang ST. Kuo HS. Hsiao CL. Lin YL. Bioorg. Med. Chem.  2002,  10:  1947 
    Google Scholar
  • 10 Chung KB. Tomoi M. J. Polym. Sci., Part A: Polym. Chem.  1992,  30:  1089 
    Google Scholar
  • 11 Weber E. Vögtle F. Top. Curr. Chem.  1981,  98:  14 
    Google Scholar
  • 12 Gokel GW. Trafton JE. Cation Binding by Lariat Ethers, In Cation Binding by Macrocycles   Inoue Y. Gokel GW. Marcel Dekker; New York: 1990.  p.253 ; see also p. 279
    Google Scholar
  • 13 Foroughifar N. Mobinikhaledi A. Ebrahimi S. Moghanian H. Bodaghi Fard MA. Kalhor M. Tetrahedron Lett.  2009,  50:  836 
    CrossrefGoogle Scholar
  • 14a Pellisard D. Luis R. Tetrahedron Lett.  1972,  4589 
    Google Scholar
  • 14b Overman LE. J. Org. Chem.  1972,  37:  4214 
    Google Scholar
  • 15 Sharghi H. Eshghi H. Tetrahedron  1995,  51:  913 
    CrossrefGoogle Scholar
  • 16 Morphy RJ. Parker D. Alexander R. Bains A. Came AF. Eaton MAW. Harrison A. Millican A. Philipps A. Rhind SK. Tetmas R. Weatherby D. J. Chem. Soc., Chem. Commun.  1988,  156 
    CrossrefGoogle Scholar
  • 17 Jurczak J. Kasprzyh S. Satanski P. Stankiewicz T. Lipkowski P. Tetrahedron  1993,  49:  1478 
    CrossrefGoogle Scholar
  • 18a Tabushi I. Taniguchi Y. Kado H. Tetrahedron Lett.  1977,  1049 
    Google Scholar
  • 18b Tabushi I. Okino H. Kuroda Y. Tetrahedron Lett.  1976,  4339 
    Google Scholar
  • 19 Xu PF. Sun XW. Zhang LM. Zhang ZY. J. Chem. Res., Synop.  1999,  170 
    CrossrefGoogle Scholar
  • 20 Ibrahim YA. Elwahy AHM. Elkareish GMM. J. Chem. Res., Synop.  1994,  414 
    Google Scholar