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Communication | Special issue | Vol 52, No. 2, 2000, pp.533-536
Published online, 1st January, 1970
DOI: 10.3987/COM-99-S75
A Novel Simple Method of Synthesis of 2-Amino-4-(-6-)nitroindoles via Base Promoted Condensation of m-Nitroanilines with Nitriles

Nikolai Moskalev and Mieczyslaw Makosza*

*Institute of Organic Chemistry, Polish Academy of Sciences, Kasprzaka 44, 01-224 Warsaw, Poland

Abstract

Base promoted condensation of nitrites (RCH2CN) with m-nitroanilines at room temperature results in the formation of 3-alkyl- or 3-aryl-2-amino-4-(-6-) nitroindoles. This multistep process includes presumably nucleophilic substitution of hydrogen (or halogen) in the nitroaromatic ring by the nitrile carbanion and subsequent cyclization of the ortho-aminophenylacetonitriles so formed to give the aminoindoles.