Synthesis 2004(16): 2760-2765  
DOI: 10.1055/s-2004-831164
PSP
© Georg Thieme Verlag Stuttgart · New York

Cyanoacetylation of Indoles, Pyrroles and Aromatic Amines with the Combination Cyanoacetic Acid and Acetic Anhydride

Johnny Slätt, Ivan Romero, Jan Bergman*
Unit for Organic Chemistry, Department of Biosciences, Karolinska Institute and Södertörn University College, Novum Research Park, 141 57 Huddinge, Sweden
Fax: +46(8)6089204; e-Mail: jabe@cnt.ki.se ;
Further Information

Publication History

Received 1 March 2004
Publication Date:
13 August 2004 (online)

Abstract

Cyanoacetic acid was activated with acetic anhydride and when heated this reagent reacted with a variety of both activated and deactivated pyrroles, indoles and aniline derivatives.

    References

  • 1 Güner I. Osman F. Pharmacophore Perception, Development, and Use in Drug Design   International University Line; La Jolla, California: 2000. 
  • 2 Batchelor MJ, Moffat J, David FC, Davis JM, and Hutchings MC. inventors; Celltech R & D Limited., PCT Int appl. WO  2000078731.  ; Chem. Abstr. 2000, 134, 71598
  • 3 Schroeder C. Link KP. J. Am. Chem. Soc.  1953,  75:  1886 
  • 4 Baraldi PG. Romagnoli R. Pavani MG. Nuñez MC. Tabrizi MA. Shryock JC. Leung E. Moorman AR. Uluoglu C. Iannotta V. Merighi S. Borea PA. J. Med. Chem.  2003,  46:  794 
  • 5 Smirnova NM. Cherdantseva NM. Burova OA. Nesterov VM. Safonova TS. Chem. Heterocycl. Compd.  1990,  811 
  • 6 inventors; Farbenfabriken Bayer, DE  175415.  ; Chem. Abstr. 1907, 1, 6240
  • 7 Schroeter G. Seidler C. Sulzbacher M. Kanitz R. Ber. Dtsch. Chem. Ges.  1932,  65:  432 
  • 8 Kreher R. Wagner PH. Chem. Ber.  1980,  113:  3675 
  • 9 Kappe T. Stelze HP. Ziegler E. Monatsh. Chem.  1983,  114:  953 
  • 10 Schroeter G. Finck E. Ber. Dtsch. Chem. Ges.  1938,  71:  671 
  • 11 Ingraffia F. Gazz. Chim. Ital.  1934,  64:  778 
  • 12 Ingraffia F. Gazz Chim. Ital.  1934,  64:  784 
  • 13 Fischer H. Schneller K. Zerweck W. Ber. Dtsch. Chem. Ges.  1922,  55:  2390 
  • 14 Gotor V. Liz R. Testera AM. Tetrahedron  2004,  60:  607 
  • 15 Takayama K. Iwata M. Hisamichi H. Okamoto Y. Aoki M. Niwa A. Chem. Pharm. Bull.  2002,  50:  1050 
  • 17 Shelkov R. Nahmany M. Melman A. J. Org. Chem.  2002,  67:  8975 
  • 18 Hayashi H. Ohmoto S. Somei M. Heterocycles  1997,  45:  1647 
  • 19 Walker GN. inventors; Ciba-Geigy, European Patent  156091.  ; Chem. Abstr. 1987, 106, 156268
  • 20 Walker GN. inventors; Ciba-Geigy, US Patent  4256759.  ; Chem. Abstr. 1981, 95, 7046
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Slätt, J.; Bergman, J., unpublished results.