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Synthesis 2010(2): 205-207  
DOI: 10.1055/s-0029-1217087
SHORTPAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis and Characterization of Novel 30-Membered Imine and Amine Macrocycles Derived from ortho-Aminophenyl Diamines and 2,6-Diformyl-4-chlorophenol

Hadi Amiri Rudbari*, Ali Varasteh Moradi
Department of Chemistry, Islamic Azad University of Gorgan, Gorgan, Iran
Fax: +98(174)6853400; e-Mail: hamiri1358@gmail.com;
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Publication History

Received 26 August 2009
Publication Date:
26 October 2009 (online)

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Abstract

Two novel macrocyclic tetraimine-diphenol Schiff bases were synthesized by [2+2] cyclocondensation of ortho-aminophenyl diamines [1,2-bis(2′-aminophenoxy)benzene and 1,2-bis(2′-aminophenoxy)-4-tert-butylbenzene] with 2,6-diformyl-4-chloro­phenol (dcp). Two novel tetraamine-diphenol macrocycles were obtained by reduction of the imine analogues with sodium borohydride in methanol/chloroform.

Key words

o-aminophenyl diamines - 2,6-diformyl-4-chlorophenol - Schiff base macrocycles - tetraamine-diphenol macrocycles

    References

  • 1a Fenton DE. In Advances in Inorganic and Bioinorganic Mechanisms   Vol. 2:  Sykes AG. Academic Press; London: 1983.  p.187 
    Google Scholar
  • 1b Karlin KD. Zubieta J. Copper Coordination Chemistry and Biochemistry: Biochemical and Inorganic Perspectives   Adenine Press; Guilderland NY: 1983. 
    Google Scholar
  • 1c Okawa H. Furutachi H. Fenton DE. Coord. Chem. Rev.  1998,  174:  51 
    Google Scholar
  • 1d Alexander V. Chem. Rev.  1995,  95:  273 
    Google Scholar
  • 2a Zanello P. Tamburini S. Vigato PA. Mazzocchin GA. Coord. Chem. Rev.  1987,  77:  165 
    Google Scholar
  • 2b Fenton DE. Okawa H. Perspectives on Bioinorganic Chemistry   Vol. 2:  JAI Press; London: 1993.  p.81-138  
    Google Scholar
  • 3a Adams H. Fenton DE. Haque SR. Heath SL. Ohba M. Okawa H. Spey SE. J. Chem. Soc., Dalton Trans.  2000,  1849 
    Google Scholar
  • 3b Casellato U. Tamburini S. Tomasin P. Vigato PA. Aime S. Barge A. Motta M. Chem. Commun.  2000,  145 
    Google Scholar
  • 3c Yonemura M. Okawa H. Ohba M. Fenton DE. Thompson LK. Chem. Commun.  2000,  817 
    Google Scholar
  • 3d Furutachi H. Fujinami S. Suzuki M. Okawa H. J. Chem. Soc., Dalton Trans.  1999,  2197 
    Google Scholar
  • 3e Kita S. Furutachi H. Okawa H. Inorg. Chem.  1999,  38:  4038 
    Google Scholar
  • 4a Mandal SK. Thompson LK. Nag K. Charland JP. Gabe EJ. Inorg. Chem.  1987,  26:  1391 
    Google Scholar
  • 4b Okawa H. Tadokoro M. Aratake Y. Ohba M. Shindo K. Mitsumi M. Koikawa M. Tomono M. Fenton DE. J. Chem. Soc., Dalton Trans.  1993,  253 
    Google Scholar
  • 4c Adams H. Clunas S. Fenton DE. Spey SE. J. Chem. Soc., Dalton Trans.  2003,  625 
    Google Scholar
  • 5 Shangguan G. Martell AE. Zhang Z. Reibenspies JH. Inorg. Chim. Acta  2000,  299:  47 
    CrossrefGoogle Scholar
  • 6 Kong D. Reibenspies J. Martell AE. Motekaitis RJ. Inorg. Chim. Acta  2001,  324:  35 
    CrossrefGoogle Scholar
  • 7 He H. Martell AE. Motekaitis RJ. Reibenspies JH. Inorg. Chem.  2000,  39:  1586 
    CrossrefGoogle Scholar
  • 8 Wang J. Martell AE. Motekaitis RJ. Inorg. Chim. Acta  2001,  322:  47 
    CrossrefGoogle Scholar
  • 9a Kong D. Martell AE. Motekaitis RJ. Reibenspies JH. Inorg. Chim. Acta  2001,  317:  243 
    Google Scholar
  • 9b Wang J. Kong D. Martell AE. Motekatis RJ. Reibenspies JH. Inorg. Chim. Acta  2001,  324:  194 
    Google Scholar
  • 10 Keypour H. Amiri Rudbari H. Azadbakht R. Synth. Commun.  2009,  in press
    Google Scholar
  • 11 Lodeiro C. Bastida R. Blas AD. Fenton DE. Macias A. Rodriguez A. Rodriguez-Blas T. Inorg. Chim. Acta  1998,  267:  55 
    CrossrefGoogle Scholar
  • 12 Keypour H. Azadbakht R. Amiri Rudbari H. Heydarinekoo A. Khavasi H. Transition Met. Chem.  2009,  in press
    Google Scholar
  • 13 Keypour H. Azadbakht R. Salehzadeh S. Amiri Rudbari H. Adams H. Tetrahedron Lett.  2009,  50:  169 
    CrossrefGoogle Scholar
  • 14 Esteban D. Avecilla F. Platas-Iglesias C. Mahía J. Blas AD. Rodríguez-Blas T. Inorg. Chem.  2002,  41:  4337 
    CrossrefGoogle Scholar
  • 15 Tei L. Arca M. Aragón MC. Bencina A. Blake AJ. Caltagirone C. Devillanova FA. Fornasari P. Garau A. Isaia F. Lippolis V. Schröder M. Teat SJ. Valtancoli B. Inorg. Chem.  2003,  42:  8690 
    CrossrefGoogle Scholar
  • 16 Taniguchi S. Bull. Chem. Soc. Jpn.  1984,  57:  2683 
    CrossrefGoogle Scholar
  • 17 Keypour H. Amiri Rudbari H. Azadbakht R. Abouzari Lotf E. J. Chem. Res.  2009,  361 
    CrossrefGoogle Scholar