Trifluoromethyl-containing N-acylmethylenequinone imines as novel highly electrophilic agents |
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Authors: | Victor I. Dyachenko Aleksandr S. Peregudov Nikolai D. Chkanikov |
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Affiliation: | A.N. Nesmeyanov Institute of Organoelement Compounds, the Russian Academy of Sciences, Vavilov Str. 28, 119991 Moscow, Russia |
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Abstract: | The strategy of searching for highly electrophilic agents in a class of chemically inert compounds - methylenequinone imines - was developed and successfully performed. The first representative of such electrophiles - N-acyl-α-methoxycarbonyl-α-trifluoromethyl-p-methylenequinone imine 6 - was synthesized. Its reactions with N-, O- and C-nucleophiles were investigated that gave various derivatives of α-trifluoromethyl-α-amino(oxy) acids as well as ß,ß,ß-trifluoropropionic acids. 3-Chloro-3-trifluoro-1,3-dihydroindol-2-ones were first obtained and their reactions with nucleophiles were studied with 1-aza-3-trifluoroindene-2-ones being formed as intermediates. |
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Keywords: | N-Acylmethylenequinone imines 1-Azainden-2-ones Electrophiles 1,3-Dihydroindol-2-ones |
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