S. Osipov, N. D. Chkanikov, Yu. V. Shklyaev
Sep 1, 1989
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Journal
Bulletin of the Academy of Sciences of the USSR, Division of chemical science
Abstract
The trifluoroacetylimine of methyl trifluoropyruvate regiospecifically C-alkylates furan, N-methylpyrrole, and thiophenes at the free C 2 position, indoles at the C 3 position, and l-phenyl-3-methyl-5-pyrazolone at the C 4 position. The alkylation products were converted to trifluoromethylated amino acids and their ester and amine derivatives. The C-alkylation of indoles and thiophene by the benzenesulfonylimine of methyl trifluoropyruvate was described in our previous work [I]. Details are given below for the reactions of the trifluoroacetylimine of methyl trifluoropyruvate (I) with some five-membered heterocyclic compounds~ Thiophene derivatives are selectively alkylated by imine (I) in CCI 4 at reflux at the free C 2 position to give thiophenes (II)-(Vl) in preparative yields. Furan and N-methylpyrrole undergo this reaction in chloroform from -50 to +20~ to give the C2-alkylation products (VII) and (VIII).