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A study of the Claisen—Eschenmoser reaction for hydroxymethylbenzofurans and-indoles
Authors:T I Mukhanova  S Yu Kukushkin  P Yu Ivanov  L M Alekseeva  V G Granik
Institution:(1) State Research Center of Antibiotics, 3a ul. Nagatinskaya, 117105 Moscow, Russian Federation
Abstract:N,N-Dimethylacetamide dimethyl acetal reacted with 5(7)-substituted 2-(hydroxy-methyl)benzofurans to give N,N-dimethyl-2-(2-methylbenzofuran-3-yl)acetamides. Analogous reactions with 3-(hydroxymethyl)indole and 1-hydroxy-6-methyl-1,2,3,4-tetrahydro-carbazole afforded N,N-dimethyl-3-(3-indolyl)propionamide and N, N-dimethyl-2-(6-methyl-1,2,3,4-tetrahydrocarbazol-1-yl)acetamide, respectively. Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 2, pp. 314–318, February, 2007.
Keywords:the Claisen—  Eschenmoser reaction            N  N-dimethylacetamide dimethyl acetal  benzofurans  indoles  [3  3]-sigmatropic rearrangement  acetamides
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