1-Bromo-2-trifluoroacetylcyclobutenes as novel building blocks for the construction of trifluoromethyl substituted heterocycles. Part 1: Synthesis of 5-(trifluoromethyl)-2(5H)-furanones condensed with substituted cyclobutenes |
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| Authors: | Andrey B Koldobskii Nikolay P Tsvetkov Ekaterina V Solodova Valery N Kalinin |
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| Institution: | A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Vavilov Str. 28, 119991 Moscow, Russian Federation |
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| Abstract: | The regioselective reduction of substituted 1-bromo-2-trifluoroacetylcyclobutenes by lithium aluminium hydride affords corresponding brominated alcohols, which, under the treatment of two equivalents of butyllithium, give new lithiated cyclobutenes. Their carboxylation followed by lactonization induced by trifluoroacetic anhydride appeared to be an effective approach towards 5-trifluoromethylated furanones condensed with substituted cyclobutene rings. |
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| Keywords: | Regioselective reduction Halogen-metal exchange Carboxylation Cyclization 5-(Trifluoromethyl)-furanones |
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