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Synthesis 2001(7): 1023-1026
DOI: 10.1055/s-2001-14562
PAPER
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Heteroarylazo-substituted Calix[4]arenes

Chuan-Ming Jina, Guo-Yuan Lu*a, Zhen-Sheng Wanga, Xiao-Zeng Youa, Zhong-Hua Wangb, Wei Gongb, Hou-Ming Wub
a Department of Chemistry, State Key Laboratory of Coordination Chemistry, Nanjing University, Nanjing 210093, P. R. China
b State Key Laboratory of Bio-organic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032, P. R. China
Fax: +86(25)3317761; e-Mail: nnj.lugy@jlonline.com;
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Publication History

Received 15 January 2001
Publication Date:
30 September 2004 (online)

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Abstract

This paper reports a novel method for preparing heteroarylazo- substituted calix[4]arenes, in which heteroaromatic amines were diazotized with isoamyl nitrite in EtONa-EtOH under refluxing conditions. Mono(heteroarylazo)-, bis(heteroarylazo)- and tetrakis(heteroarylazo)-substituted calix[4]arenes were obtained as main product by diazo-coupling in different molar ratio to calix[4]arenes under pH 7-9 in non-aqueous solution at 0-5 °C. Based on the method, eight novel heteroarylazo-substituted calix[4]arenes have been synthesized by diazo-coupling reaction of calix[4]arene with diazonium salt solutions of 4-aminopyridine or 2-aminothiazole.

Key words

calix[4]arene - diazo coupling - isoamyl nitrite - synthesis

    References

  • 1 Vicens J. Bhömer V. Calixarene-A Versatile Class of Macrocyclic Compounds   Kluwer; Dordrecht: 1991. 
  • 2 Pochini A. Ungaro R. Calix[4]arenes and Related Hosts, In Comprehensive Supramolecular Chemistry   Lehn J.-M. Vögtle F. Pergamon; New York: 1996.  p.103-142  
  • 3 Ikeda A. Shinkai S. Chem. Rev.  1997,  97:  1713 
    CrossrefSearch in Google Scholar
  • 4 Shinkai S. Araki K. Shibata J. Tsugawa D. Manabe O. Chem. Lett.  1989,  931 
  • 5 Shinkai S. Araki K. Shibata J. Tsugawa D. Manabe O. J. Chem. Soc., Perkin Trans.1  1990,  3333 
  • 6 Nomura E. Taniguchi H. Tamura S. Chem. Lett.  1989,  1125 
  • 7 Morita Y. Agawa T. Nomura E. Taniguchi H. J. Org. Chem.  1992,  57:  3658 
    Search in Google Scholar
  • 8 Tyson JC. Moore JL. Hughes KD. Collard DM. Langmuir  1997,  13:  2068 
    CrossrefSearch in Google Scholar
  • 9 Yeh M.-L. Tang F.-S. Chen S.-L. Liu W.-C. Lin L.-G. J. Org. Chem.  1994,  59:  754 
    Search in Google Scholar
  • 10 Takamura N. Mizoguchi T. Koga K. Yamada S. Tetrahedron  1975,  31:  227 
    CrossrefSearch in Google Scholar
  • 11 Iwamoto K. Araki K. Shinkai S. Tetrahedron  1991,  47:  4325 
    CrossrefSearch in Google Scholar
  • 12 Jaime C. deMendoza J. Prados P. Nieto PM. Sanchez C. J. Org. Chem.  1991,  56:  3372 
    CrossrefSearch in Google Scholar
  • 13 Lu GY. Li Q. Liu F. Wan XB. Chin. J. Chem.  2000,  18:  207 
    Search in Google Scholar
  • 14 Yang XG. McBranch D. Swanson B. Li DQ. Angew. Chem., Int. Ed. Engl.  1996,  35:  538 
    Search in Google Scholar
  • 15 Kelderman E. Derhaeg L. Heesink GJT. Verboom W. Engbersen JFJ. VanHulst NF. Persoons A. Reinhoudt DN. Angew. Chem., Int. Ed. Engl.  1992,  31:  1075 
    Search in Google Scholar
  • 16 VanLoon JD. Arduini A. Coppi L. Verboom W. Pochini A. Ungaro R. Harkema S. Reinhoudt DN. J. Org. Chem.  1990,  55:  5639 
    Search in Google Scholar