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DOI: 10.1055/s-0030-1258422
Synthesis of 2-Aminoindole-3-carboxylic Acid Derivatives by the Copper(I) Iodide Catalyzed Reaction of N-(2-Iodophenyl)formamides with Malononitrile or Cyanoacetates
Publikationsverlauf
Publikationsdatum:
03. Februar 2011 (online)
Abstract
An efficient method for the synthesis of 2-aminoindole-3-carbonitriles and 2-aminoindole-3-carboxylates by the reaction of N-(2-iodophenyl)formamides with malononitrile and cyanoacetates, respectively, in the presence of a catalytic amount of copper(I) iodide using potassium carbonate as a base is reported.
Key words
2-aminoindole-3-carboxylates - 2-aminoindole-3-carbonitriles - N-(2-iodophenyl)formamides - copper(I) iodide - coupling
- 1a
Willemann C.Grünert R.Bednarski PJ.Troschütz R. Bioorg. Med. Chem. 2009, 17: 4406Reference Ris Wihthout Link - 1b
Forbes IT.Johnson CN.Thompson M. J. Chem. Soc., Perkin Trans. 1 1992, 275Reference Ris Wihthout Link - 1c
Gangjee A.Zaware N.Raghavan S.Ihnat M.Shenoy S.Kisliuk RL. J. Med. Chem. 2010, 53: 1563Reference Ris Wihthout Link - 2
Grob CA.Weissbach O. Helv. Chim. Acta 1961, 44: 1748 - 3a A
synthesis via Nenitzescu reaction had appeared:
Landwehr J.Troschuetz R. Synthesis 2005, 2414Reference Ris Wihthout Link - 3b
For other methods, see refs. 11 and 12.
Reference Ris Wihthout Link - 4
Okuro K.Furuune M.Miura M.Nomura M. J. Org. Chem. 1993, 58: 7606 - 6
Xiao W.-J.Alper H. J. Org. Chem. 1999, 64: 9646 - 7
Lizos D.Tripoli R.Murphy JA. Chem. Commun. 2001, 2732 - 8
Fukamachi S.Konishi H.Kobayashi K. Synthesis 2010, 1593 - 9
Petit GR.Thomson EG. J. Org. Chem. 1959, 24: 895 - 10
Hays SJ.Caprathe BW.Gilmore JL.Amin N.Emmerling MR.Michael W.Nadimpalli R.Nath R.Raser KJ.Stafford D.Watson D.Wang K.Jaen JC. J. Med. Chem. 1998, 41: 1060 - 11
Eger K.Lanzner W.Rothenhaeusler K. Liebigs Ann. Chem. 1993, 465 - 12
Munshi KL.Kohl H.De Souza NJ. J. Heterocycl. Chem. 1977, 14: 1145 - 13
Diana P.Barraja P.Lauria A.Almerico AM.Dattolo G.Cirrincione G. Tetrahedron 2000, 56: 5177
References
Before subjection to column chromatography on silica gel, the mixture must be filtered through a small pad of neutral alumina. Omission of this filtration procedure did not give 3a in a satisfactory purity. For details, see the experimental section.