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Synthesis 2009(21): 3603-3610  
DOI: 10.1055/s-0029-1216996
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Straightforward Synthesis of 2-(1-Vinyl-1H-pyrrol-2-yl)-1H-benzimidazoles from 1-Vinyl-1H-pyrrole-2-carbaldehydes and o-Phenylenediamine

Boris A. Trofimov*, Andrei V. Ivanov, Elena V. Skital’tseva, Alexander M. Vasil’tsov, Igor A. Ushakov, Konstantin B. Petrushenko, Al’bina I. Mikhaleva
A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky St., Irkutsk 664033, Russian Federation
Fax: +7(3952)419346; e-Mail: boris_trofimov@irioch.irk.ru;
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Publication History

Received 18 June 2009
Publication Date:
08 September 2009 (online)

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Abstract

Hitherto inaccessible 1-vinylpyrrole-benzimidazole ensembles have been synthesized by the condensation of 1-vinyl-1H-pyrrole-2-carbaldehydes with o-phenylenediamine either directly or via the intermediate Schiff bases of the 1-vinyl-1H-pyrrole-2-carbaldehydes (1% TFA, DMSO, air atmosphere, 60-70 ˚C, 1 h) in yields up to 89%, the intermediate Schiff bases of exclusively E configuration being isolated in 91-98% yield (1% TFA, DMSO, r.t., 30 min). The synthesized 2-(1-vinyl-1H-pyrrol-2-yl)-1H-benzimidazoles are intensely fluorescent, covering the practically important blue region (λmax 343-417 nm, Stokes shift 31-91 nm).

Key words

1-vinyl-1H-pyrrole-2-carbaldehydes - pyrrolylbenzimidazoles - o-phenylenediamine - Schiff bases - oxidative condensation

    References

  • 1a Dykstra CC, Perfect J, Boykin DW, Wilson WD, and Tidwell RR. inventors; US Patent  5639755.  ; Chem. Abstr. 1997, 126, 131457x
  • 1b Dykstra CC, Boykin D, and Tidwell RR. inventors; PCT Int. Appl. WO 98 38  170.  ; Chem. Abstr. 1998, 129, 230727d
  • 1c Renneberg D. Dervan PB. J. Am. Chem. Soc.  2003,  125:  5707 
    Search in Google Scholar
  • 1d Viger A. Dervan PB. Bioorg. Med. Chem.  2006,  14:  8539 
    Search in Google Scholar
  • 1e Starčević K. Kralj M. Ester K. Sabol I. Grce M. Pavelić K. Karminski-Zamola G. Bioorg. Med. Chem.  2007,  15:  4419 
    Search in Google Scholar
  • 2 Batista RMF. Costa SPG. Belsley M. Raposo MM. Tetrahedron  2007,  63:  9842 
    CrossrefSearch in Google Scholar
  • 3 Haugland RP, and Kang HC. inventors; (Molecular Probes, Inc.) US Patent  5248782.  ; Chem. Abstr. 1994, 120, 32877d
  • 4a El’chaninov MM. Simonov AM. Oleinikova LYa. Chem. Heterocycl. Compd. (Engl. Transl.)  1980,  16:  59 
    Search in Google Scholar
  • 4b Jones RA. Quintanilla-Lopez G. Taheri SAN. Hania MM. Öztürk O. Zuilhof H. ARKIVOC  2000,  (iii):  382 
    Search in Google Scholar
  • 4c Lin S. Yang L. Tetrahedron Lett.  2005,  46:  4315 
    Search in Google Scholar
  • 4d Chakrabarty M. Mukherji A. Mukherjee R. Arima S. Harigaya Y. Tetrahedron Lett.  2007,  48:  5239 
    Search in Google Scholar
  • 4e Du L.-H. Wang Y.-G. Synthesis  2007,  675 
  • 5 Szydlo F. Andrioletti B. Rose E. Duhayon C. Tetrahedron Lett.  2008,  49:  3749 
    CrossrefSearch in Google Scholar
  • 6 De Selms RC. J. Org. Chem.  1962,  27:  2163 
    CrossrefSearch in Google Scholar
  • 7 George B. Papadopoulos EP. J. Org. Chem.  1977,  42:  441 
    CrossrefSearch in Google Scholar
  • 8 Yang D. Fokas D. Li J. Yu L. Baldino CM. Yang D. Fokas D. Li J. Yu L. Baldino CM. Synthesis  2005,  47 
    Thieme Connect
  • 9a Tedeschi RJ. Encyclopedia of Physical Science and Technology   Vol. 1:  Academic Press; San Diego: 1992.  p.27 
    Search in Google Scholar
  • 9b Gonzalez F. Sanz-Cervera JF. Williams RM. Tetrahedron Lett.  1999,  40:  9 
    Search in Google Scholar
  • 9c Abele E. Lucevics E. Chem. Heterocycl. Compd. (Engl. Transl.)  2001,  37:  141 
    Search in Google Scholar
  • 9d Trofimov BA. In The Chemistry of Heterocyclic Compounds   Vol. 48:  Jones RA. Wiley & Sons; New York: 1992.  p.131 
    Search in Google Scholar
  • 10 Trofimov BA. Mikhaleva AI. Vasil’ev AN. Lopyrev VA. Titova IA. Bzhezovskii VM. Sigalov MV. Khim. Geterotsikl. Soedin.  1981,  1422 ; Chem. Abstr. 1982, 96, 199581
  • 11a Mikhaleva AI. Zaitsev AB. Ivanov AV. Schmidt EYu. Vasil’tsov AM. Trofimov BA. Tetrahedron Lett.  2006,  47:  3693 
    Search in Google Scholar
  • 11b Mikhaleva AI. Ivanov AV. Skital’tseva EV. Ushakov IA. Vasil’tsov AM. Trofimov BA. Synthesis  2009,  587 
  • 12 Vasil’tsov AM. Ivanov AV. Ushakov IA. Mikhaleva AI. Trofimov BA. Synthesis  2007,  452 
    Thieme Connect
  • 13a Trofimov BA. Mikhaleva AI. Morozova LV. Vasil’ev AN. Sigalov MV. Khim. Geterotsikl. Soedin.  1983,  269 ; Chem. Abstr. 1983, 98, 215442
  • 13b Trofimov BA. Morozova LV. Sigalov MV. Mikhaleva AI. Markova MV. Makromol. Chem.  1987,  188:  2251 
    Search in Google Scholar
  • 13c Trofimov BA. Markova MV. Morozova LV. Mikhaleva AI. ARKIVOC  2001,  (ix):  24 
    Search in Google Scholar
  • 14 Mikhaleva AI. Ivanov AV. Vasil’tsov AM. Ushakov IA. Ma JS. Yang G. Chem. Heterocycl. Compd. (Engl. Transl.)  2008,  44:  1117 
    CrossrefSearch in Google Scholar
  • 15a Wu Z. Chen Q. Xiong S. Xin B. Zhao Z. Jiang L. Ma JS. Angew. Chem.  2003,  115:  3393 
    Search in Google Scholar
  • 15b Wu Z. Chen Q. Yang G. Xiao C. Liu J. Yang S. Ma JS. Sens. Actuators, B  2004,  99:  511 
    Search in Google Scholar
  • 15c Yang L. Shan X. Chen Q. Wang Z. Ma JS. Eur. J. Inorg. Chem.  2004,  1474 
  • 15d Zhang G. Yang G. Ma JS. In New Developments in Organometallic Chemistry Research   Cato MA. Nova Science Publishers; New York: 2006.  p.63 
  • 16 Omura K. Swern D. Tetrahedron  1978,  34:  1651 
    CrossrefSearch in Google Scholar
  • 17 Petrushenko IK. Smirnov VI. Petrushenko KB. Schmidt EYu. Zorina NV. Rusakov YuYu. Vasil’tsov AM. Mikhaleva AI. Trofimov BA. Russ. J. Gen. Chem. (Engl. Transl.)  2007,  77:  1386 
    CrossrefSearch in Google Scholar
  • 18 Vasil’tsov AM. Schmidt EYu. Mikhaleva AI. Zorina NV. Zaitsev AB. Petrova OV. Krivdin LB. Petrushenko KB. Ushakov IA. Pozo-Conzalo C. Pomposo JA. Grande H.-J. Tetrahedron  2005,  61:  7756 
    CrossrefSearch in Google Scholar