Abstract
Abstract Polyfluoroketones form stable N-alkylation products with amines [H.E. Simmons and D.W. Wiley, J. Am. Chem. Soc., 30 (1960) 2288], which are intermediates in the Mannich reaction. However, we have not found information about usage of these compounds in that reaction. We have shown that 2-hydroxy-2-trifluoromethylpiperazin-3-one ( A ), formed by interaction of methyl trifluoropyruvate and 1,2-ethylenediamine [V.I. Saloutin, I A. Pyterskick, K.I. Pashkiewich et al., Izv. AN USSR Ser. Chim. No. 11 (1983) 2568], easily reacts with indole giving 2-(3-indolyl)-2-trifluoromethylpiperazin -3-one ( B ) under Mannich reaction conditions. Under analogous conditions A reacts with 1-phenyl-3-methylpyrazol-5-one, N-methylpyrrole, derivatives of thiophene, furane, phenol, some enamines and ketones. The peculiarities of these reactions are discussed.
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