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Synthesis 2007(1): 33-38  
DOI: 10.1055/s-2006-950368
PAPER
© Georg Thieme Verlag Stuttgart · New York

A General Synthesis of Furo[3,2-c][1,2,4]triazolo[1,5-a]azepine and Furo[2,3-f][1,2,4]triazolo[1,5-a]azepine Derivatives

Qingqing Meng, Hexiang Bai, Quanrui Wang*, Fenggang Tao
Department of Chemistry, Fudan University, 200433 Shanghai, P. R. of China
Fax: +86(21)65641740; e-Mail: qrwang@fudan.edu.cn;
Further Information

Publication History

Received 26 July 2006
Publication Date:
13 November 2006 (online)

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Abstract

Derivatives of two new heterocyclic systems, namely furo­[3,2-c][1,2,4]triazolo[1,5-a]azepinium salts and furo[2,3-f][1,2,4]triazolo[1,5-a]azepinium picrates, were synthesized from bicyclic azo compounds and nitriles in the presence of antimony pentachloride or aluminum chloride. The crystal diffraction analysis of an example product is reported and confirms the structure.

Key words

1-aza-2-azoniaallene cations - cycloaddition - nitriles - ring enlargement - furotriazoloazepine

    References

  • 1 Cho H. Murakami K. Nakanishi H. Fujisawa AK. Isoshima H. Niwa M. Hayakawa K. Hase Y. Uchida I. Watanabe H. Wakitani K. Aisaka K. J. Med. Chem.  2004,  47:  101 
    CrossrefGoogle Scholar
  • 2 Cho H, and Wakitani K. inventors; PCT Int. Appl. WO  9717349.  ; Chem. Abstr. 1997, 127, 5023
  • 3 Cho H. Murakami K. Nakanishi H. Isoshima H. Hayakawa K. Uchida I. Heterocycles  1998,  48:  919 
    CrossrefGoogle Scholar
  • 4 Janssens FE, Lacrampe JFA, and Pilatte INC. inventors; PCT Int. Appl. WO  9413681.  ; Chem. Abstr. 1994, 121, 205360
  • 5 Cortes EC. Romero EC. Taylor AD. Garcia MCL. Trends Heterocycl. Chem.  1995,  4:  25 ; Chem. Abstr. 1997, 126, 104045
    Google Scholar
  • 6 Martinez LR. Zarraga JGA. Duran ME. Apam MTR. Canas R. Bioorg. Med. Chem. Lett.  2002,  12:  1675 
    CrossrefGoogle Scholar
  • 7 Liu X. Wang Q. Liu Y. Fan Y. Zing Z. Synthesis  2000,  435 
    Article in Thieme ConnectGoogle Scholar
  • 8 Liu X. Liu Y. Wang Q. Zou J. Synth. Commun.  2000,  30:  119 
    CrossrefGoogle Scholar
  • 9 Wang Q. Li Z. Yang H. Li F. Ding Z. Tao F. Synthesis  2003,  1231 
    Article in Thieme ConnectGoogle Scholar
  • 10 Shiraishi M, and Fukumoto S. inventors; PCT Int. Appl. WO  9942442.  ; Chem. Abstr. 1999, 131, 720
  • 11 Lipshutz BH. Chem. Rev.  1986,  86:  795 
    CrossrefGoogle Scholar
  • 12 Iffland DC. Salisbury L. Schaefer WR. J. Am. Chem. Soc.  1961,  83:  747 
    CrossrefGoogle Scholar
  • 13 Wang Q. Jochims JC. Kohlbrandt S. Dahlenburg L. Al-Talib M. Hamed A. Ismail AE. Synthesis  1992,  710 
    Article in Thieme ConnectGoogle Scholar
  • 14a Gstach H. Seil P. Schantl JG. Gieren A. Hubner T. Wu J. Angew. Chem.  1986,  98:  1111 
    CrossrefGoogle Scholar
  • 14b Gstach H. Seil P. Schantl JG. Gieren A. Hubner T. Wu J. Angew. Chem., Int. Ed. Engl.  1986,  25:  1132 
    CrossrefGoogle Scholar
  • 15 For a review with respect to oximes derived from bicyclic ketones, see: Krow GR. Tetrahedron  1981,  37:  1283 
    CrossrefGoogle Scholar
  • 16 For a theoretical study on this rearrangement, see: Wei M. Fang D. Liu R. J. Org. Chem.  2002,  67:  7432 
    CrossrefGoogle Scholar
  • 17 Liu X. Liu Y. Ding Z. Wang Q. Zhang C. J. Heterocycl. Chem.  2000,  37:  287 
    CrossrefGoogle Scholar
  • 18 Mintz MJ. Walling C. Org. Synth., Coll. Vol. V  1973,  184 
    Google Scholar