Synthesis 2010(8): 1311-1314  
DOI: 10.1055/s-0029-1218655
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A New Synthesis of Functionalized 2,2′-Biimidazoles

Kevin Stippicha, Robert Kretschmera, Rainer Beckert*a, Helmar Goerlsb
a Institute of Organic and Macromolecular Chemistry, Humboldtstr. 10, 07743 Jena, Germany
b Institute of Inorganic and Analytical Chemistry, August-Bebel-Str. 2, 07743 Jena, Germany
Fax: +493641948212; e-Mail: Rainer.Beckert@uni-jena.de;
Further Information

Publication History

Received 12 November 2009
Publication Date:
29 January 2010 (online)

Abstract

A new two-step synthesis of N,N′-disubstituted 2,2′-biimidazoles from bisimidoyl chlorides is reported. The bisimidoyl chlorides react smoothly with (2,2-dimethoxyethyl)amine to give bisamidines that are subsequently cyclized to give the corresponding biimidazoles.

    References

  • 1a Tadokoro M. Isobe K. Uekusa H. Ohashi Y. Toyoda J. Tashiro K. Nakasuji K. Angew. Chem.  1999,  111:  102 
  • 1b Goulle V. Thummel RP. Inorg. Chem.  1990,  29:  1767 
  • 2 Causey CP. Allen WE. J. Org. Chem.  2002,  67:  5963 
  • 3 Allen WE. Fowler CJ. Lynch VM. Sessler JL. Chem. Eur. J.  2001,  7,; 721 
  • 4 Nonell S. Borrell JI. Borros S. Colominas C. Rey O. Rubio N. Sanchez-Garcia D. Teixido J. Eur. J. Org. Chem.  2003,  1635 
  • 5 Melloni P. Fusar-Bassini D. Logemann W. Forgiane A. Dradi E. DeCarneri I. Bianchi A. Trane F. Eur. J. Med. Chem.  1975,  10:  514 
  • 6a Shi Z. Thummel RP. Tetrahedron Lett.  1995,  36:  2741 
  • 6b Thummel RP. Goulle V. Chen B. J. Org. Chem.  1989,  54:  3057 
  • 6c Herrmann WA. Elison M. Fischer J. Köcher C. Artus GR. Chem. Eur. J.  1996,  2:  772 
  • 6d Taton TA. Chen P. Angew. Chem.  1996,  108:  1098 
  • 6e Ames JR. Houghtaling M. A. Terrian DL. Mitchell TP. Can. J. Chem.  1997,  75:  28 
  • 7a Kuhn R. Blau W. Liebigs Ann. Chem.  1957,  605:  32 
  • 7b Fieselmann B. Hendrickson D. Inorg. Chem.  1978,  17:  2078 
  • 7c Nurgatin VV. Ginzburg BM. Sharnin GB. Polyanskii VF. Khim. Geterotsikl. Soedin.  1987,  8:  1069 ; Chem. Abstr. 1988, 109, 37778e
  • 7d Duranti E. Balsamini C. Synthesis  1974,  815 
  • 7e Matthews DP. Whitten JP. McCarthy JR. Synthesis  1986,  336 
  • 8a Sanchez-Garcia D. Borros S. Nonell S. Borrell JI. Colominas C. Teixido J. J. Heterocycl. Chem.  2002,  39:  733 
  • 8b Whitten JP. Matthews DP. McCarthy JR. Barbuch RJ. J. Heterocycl. Chem.  1988,  25:  1845 
  • 9 Welzel T. Beckert R. Fischer R. Rau S. Walther D. Görls H. Tetrahedron  2006,  62:  731 
  • 10 Buehrdel G. Beckert R. Petrlikova E. Herzigova P. Klimesova V. Fleischhauer J. Goerls H. Synthesis  2008,  3071 
  • 11 Lindauer D. Beckert R. Görls H. Fehling P. Döring M. J. Prakt. Chem./Chem.-Ztg.  1995,  337:  143 
  • 13 Otwinowski Z. Minor W. In Methods in Enzymology   Vol. 276:  Carter CW. Sweet RM. Academic Press; San Diego: 1997.  p.307 
  • 14 Sheldrick G. M.; Acta Crystallogr., Sect. A; 1990, 46: 467
  • 15 Sheldrick GM. SHELX97 [Includes SHELXS97, SHELXL97 and CIFTAB]: Programs for Crystal Structure Analysis (Release 97-2)   Institut für Anorganische Chemie der Universität; Göttingen (Germany): 1998. 
12

COLLECT, Data Collection Software, Nonius BV: Delft, 1998.

16

Crystallographic data for compounds 3b and 5 have been deposited with the Cambridge Crystallographic Data Centre as supplementary publications CCDC-752317 and CCDC-752318, respectively; copies can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44(1223)336033 or email: deposit@ccdc.cam.ac. uk].