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Communication | Regular issue | Vol 24, No. 5, 1986, pp.1209-1213
Published online, 1st January, 1970
DOI: 10.3987/R-1986-05-1209
Reaction of the 2-Nitroenamine in Acid

Adam Krówczynski and Lech Kozerski*

*Institute of Organic Chemistry, Polish Academy of Sciences, ul. Kasprzaka 44/52, P.O.Box 58, PL-01-224 Warszawa 42, Poland

Abstract

2-Nitroenamines bearing heteroaryl substituents on enamine nitrogen rearrange in acids to amidooxime of the pyruvic acid or give the products of the intramolecular cyclization, di- and triaza-indenes, whereas N-aryl substituted substrates yield quinoxaline oxides. Nitronic acid of the 2-nitroenamine is suggested as a primary reactive species in acid solution. 13C and 15N NMR data are discussed which provide the evidence for this intermediate.