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Synthesis 2012(2): 235-240  
DOI: 10.1055/s-0031-1289968
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Isocyanide-Based Four-Component Synthesis of Benzo[a]pyrano[2,3-c]phenazines

Tayebeh Amanpour, Peiman Mirzaei, Ayoob Bazgir*
Department of Chemistry, Shahid Beheshti University, General Campus, Tehran 1983963113, Iran
Fax: +98(22)431663; e-Mail: a_bazgir@sbu.ac.ir;
Further Information

Publication History

Received 4 October 2011
Publication Date:
15 December 2011 (online)

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Abstract

An efficient and simple method for the synthesis of biologically interesting benzo[a]pyrano[2,3-c]phenazines by a four-component reaction of o-phenylenediamines, 2-hydroxynaphthalene-1,4-dione, isocyanides, and dialkyl acetylenedicarboxylates in N,N-dimethylformamide at 100 ˚C is reported.

Key words

isocyanide - benzo[a]pyrano[2,3-c]phenazine - dialkyl acetylenedicarboxylates - phenazine - phenylenediamines

    References

  • 1 Multicomponent Reactions   Zhu J. Bienaymé H. Wiley-VCH; Weinheim: 2005. 
    Google Scholar
  • 2 Tietze LF. Modi A. Med. Res. Rev.  2000,  20:  304 
    Google Scholar
  • 3a Dömling A. Chem. Rev.  2006,  106:  17 
    Google Scholar
  • 3b Dömling A. Ugi I. Angew. Chem. Int. Ed.  2000,  39:  3168 
    Google Scholar
  • 4 Shaabani A. Maleki A. Mofakham H. Khavasi HR. J. Comb. Chem.  2008,  10:  323 
    Google Scholar
  • 5 Fujiwara S.-I. Asanuma Y. Shin-Ike T. Kambe N. J. Org. Chem.  2007,  72:  8087 
    Google Scholar
  • 6 Yavari I. Esnaashari M. Synthesis  2005,  1049 
    Google Scholar
  • 7 Nair V. Vinod AU. Abhilash N. Menon RS. Santhi V. Varma RL. Viji S. Mathew S. Srinivas R. Tetrahedron  2003,  59:  10279 
    Google Scholar
  • 8 Teimouri MB. Mansouri F. J. Comb. Chem.  2008,  10:  507 
    Google Scholar
  • 9 Laursen JB. Nielsen J. Chem. Rev.  2004,  104:  1663 
    Google Scholar
  • 10 Makgatho M. Anderson R. O’Sullivan J. Egan T. Freese J. Cornelius N. Van Rensburg C. Drug Dev. Res.  2000,  50:  195 
    Google Scholar
  • 11 Andrade-Nieto V. Goulart M. da Silva JF. da Silva MJ. Pinto M. Pinto A. Zalis M. Carvalho L. Krettli A. Bioorg. Med. Chem. Lett.  2004,  14:  1145 
    Google Scholar
  • 12 Neves-Pinto C. Malta V. Pinto M. Santos R. Castro S. Pinto A. J. Med. Chem.  2002,  45:  740 
    Google Scholar
  • 13 Cartwright D. Chilton W. Benson D. Appl. Microbiol. Biotechnol.  1995,  43:  211 
    Google Scholar
  • 14 Muller M. Sorrell T. Prostaglandins  1995,  50:  301 
    Google Scholar
  • 15 Rewcastle G. Denny W. Baguley B. J. Med. Chem.  1987,  30:  843 
    Google Scholar
  • 16 Funayama S. Eda S. Komiyama K. Omura S. Tetrahedron Lett.  1989,  30:  3151 
    Google Scholar
  • 17 Wang S. Miller W. Milton J. Vicker N. Stewart A. Charlton P. Mistry P. Hardick D. Denny W. Bioorg. Med. Chem. Lett.  2002,  12:  415 
    Google Scholar
  • 18 Gamage S. Spicer J. Rewcastle G. Milton J. Sohal S. Dangerfield W. Mistry P. Vicker N. Charlton P. Denny W. J. Med. Chem.  2002,  45:  740 
    Google Scholar
  • 19 Lee HJ. Kim JS. Park SY. Suh ME. Kim HJ. Seo EK. Lee CO. Bioorg. Med. Chem.  2004,  12:  1623 
    Google Scholar
  • 20 Kim JS. Rhee H.-K. Park HJ. Lee I.-K. Lee SK. Suh M.-E. Lee HJ. Ryu C.-K. Park Choo HY. Bioorg. Med. Chem.  2007,  15:  451 
    Google Scholar
  • 21 Ye L. Zhang H. Xu H. Zou Q. Cheng C. Dong D. Xu Y. Li R. Bioorg. Med. Chem. Lett.  2010,  20:  7369 
    Google Scholar
  • 22 Wang S. Miller W. Milton J. Vicker N. Stewart A. Charlton P. Mistry P. Hardick D. Denny WA. Bioorg. Med. Chem. Lett.  2002,  12:  415 
    Google Scholar
  • 23 Zamaratzki E. Chattopadhyaya J. Tetrahedron  1998,  54:  8183 
    Google Scholar
  • 24 Hosseiny Davarani SS. Fakhari AR. Shaabani A. Ahmar H. Maleki A. Sheijooni Fumani N. Tetrahedron Lett.  2008,  49:  5622 
    Google Scholar
  • 25 Gamage SA. Rewcastle GW. Baguley BC. Charlton PA. Denny WA. Bioorg. Med. Chem.  2006,  14:  1160 
    Google Scholar
  • 26 Lee H.-J. Kim JS. Park S.-Y. Suh M.-E. Kim HJ. Seo E.-K. Lee C.-O. Bioorg. Med. Chem.  2004,  12:  1623 
    Google Scholar
  • 27 Lavaggi ML. Nieves M. Cabrera M. Olea-Azar C. de Ceráin AL. Monge A. Cerecetto H. González M. Eur. J. Med. Chem.  2010,  45:  5362 
    Google Scholar
  • 28 Pérez-Sacau E. Soto-Delgado J. Estévez-Brauna A. Ravelo G. Tetrahedron  2005,  61:  437 
    Google Scholar
  • 29 Wang S.-L. Wu FY. Cheng C. Zhang G. Liu Y.-P. Jiang B. Shi F. Tu S.-J. ACS Comb. Sci.  2011,  13:  135 
    Google Scholar
  • 30 Sadjadi S. Heravi MM. Tetrahedron  2011,  67:  2707 ; and references cited therein
    Google Scholar
  • 31 Jadidi K. Ghahremanzadeh R. Bazgir A. J. Comb. Chem.  2009,  11:  341 
    Google Scholar
  • 32 Ghahremanzadeh R. Sayyafi M. Ahadi S. Bazgir A. J. Comb. Chem.  2009,  11:  393 
    Google Scholar
  • 33 Akbarzadeh R. Mirzaei P. Bazgir A. J. Organomet. Chem.  2010,  695:  2320 
    Google Scholar
  • 34 Moafi L. Ahadi S. Bazgir A. Tetrahedron Lett.  2010,  51:  6270 
    Google Scholar
  • 35 Imani Shakibaei G. Feiz A. Khavasi HR. Abolhasani Soorki A. Bazgir A. ACS Comb. Sci.  2011,  13:  96 
    Google Scholar