PDF herunterladen
Synthesis 2003(10): 1545-1548
DOI: 10.1055/s-2003-40522
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Reaction of N 1,N 2-Diarylamidines with (2,3-Diphenylcyclopropen-1-ylidene)propanedinitrile: Synthesis of [2-Arylamino-4(1H)-pyridinylidene]-propanedinitriles

Mohsen A.-M. Gomaaa, Dietrich Döpp*b
a Chemistry Department, Faculty of Science, Minia University, El-Minia 61519, Egypt
b Institut für Chemie, Universität Duisburg-Essen, 47048 Duisburg, Germany
Fax: +49(203)3794192; e-Mail: doepp@uni-duisburg.de;
Weitere Informationen

Publikationsverlauf

Received 7 February 2003
Publikationsdatum:
08. Juli 2003 (online)

    Lizenzen und Reprints Alle Artikel dieser Rubrik

Abstract

A series of new [1-aryl-2-arylamino-5,6-diphenyl-4(1H)-pyridinylidene)propanedinitriles 3a-e has been synthesized by the reaction of N 1,N 2-diarylamidines 1a-e with (2,3-diphenylcyclopropen-1-ylidene)propanedinitrile (2). Structures of 3a-e have been assigned on the basis of NMR spectra and NOE experiments.

Key words

pyridines - regioselectivity - ring expansion - cycloaddition - dicyanomethylene compounds

    References

  • 1a Mayler WG. Calcium Antagonists   Academic Press; London: 1989. 
  • 1b Goldmann S. Stoltefuß J. Angew. Chem., Int. Ed. Engl.  1991,  30:  1559 ; Angew. Chem. 1991, 103, 1587
    Suche in Google Scholar
  • 2 Triggle DJ. Longs DA. Jamis RA. Med. Res. Rev.  1988,  9:  123 
    Suche in Google Scholar
  • 3 Omote Y. Kue K.-T. Sugiyama N. Bull. Chem. Soc. Jpn.  1967,  40:  1695 
    Suche in Google Scholar
  • 4 Eiden F. Peter P. Arch. Pharm. (Weinheim, Ger.)  1964,  297:  1 
    Suche in Google Scholar
  • 5 Gewald K. Schindler R. J. Prakt. Chem.  1990,  332:  223 
    CrossrefSuche in Google Scholar
  • 6 Eicher T. Freihoff W. Synthesis  1986,  908 
    Thieme Connect
  • 7 Eicher T. Abel M. Synthesis  1987,  542 
    Thieme Connect
  • 8 Eicher T. Pfister T. Urban M. Chem. Ber.  1980,  113:  424 
    Suche in Google Scholar
  • 9a Kalinowski H.-O. Berger S. Braun S. ¹³ C NMR Spektroskopie   Thieme; Stuttgart: 1984.  p.121 
  • 9b Kalinowski H.-O. ¹³ C NMR Spektroskopie   Thieme; Stuttgart: 1984.  p.347 
  • 9c Kalinowski H.-O. ¹³ C NMR Spektroskopie   Thieme; Stuttgart: 1984.  p.472 
  • 10a Claridge TW. High Resolution NMR Techniques in Organic Chemistry   Pergamon; Oxford: 1999.  p.139-142  
  • 10b Claridge TW. High Resolution NMR Techniques in Organic Chemistry   Pergamon; Oxford: 1999.  p.244-251  
  • 11 Breitmaier E. Bauer G. ¹³ C NMR-Spektroskopie   Thieme; Stuttgart: 1977. 
  • 12 Eicher T. Weber J. Knopf J. Liebigs Ann. Chem.  1978,  1222 
  • 13 Pfau M. Chiriacescu M. Revial G. Tetrahedron Lett.  1993,  34:  327 
    Suche in Google Scholar
  • 14 Taylor EC. Erhart WA. J. Org. Chem.  1963,  28:  1108 
    Suche in Google Scholar
  • 15 Eicher T. Pfister T. Krüger N. Org. Prep. Proced. Int.  1974,  6:  63 
    Suche in Google Scholar