beta-Bromodifluoromethyl beta-enaminoketones: versatile synthetic intermediates for synthesis of CF2-containing compounds

A series of N-aryl beta-bromodifluoromethyl beta-enaminoketones were regioselectively synthesized in good yield by the reaction of N-aryl bromodifluoroacetimidoyl chlorides with methyl ketones. beta-Bromodifluoromethyl beta-enammoketones smoothly cyclized to give a novel class of cyclic (2,2-difluor...

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Bibliographic Details
Published inTetrahedron letters Vol. 46; no. 32; pp. 5357 - 5360
Main Authors Wu, YM, Li, Y, Deng, J
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 08.08.2005
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
halophilic substitution
ROUTE
enaminoketones
REAGENTS
ACIDS
REACTIVITY
cyclization
ALCOHOLS
KETONES
ENAMINONES
HETEROCYCLES
bromodifluoromethyl
ESTERS
DERIVATIVES
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Summary:A series of N-aryl beta-bromodifluoromethyl beta-enaminoketones were regioselectively synthesized in good yield by the reaction of N-aryl bromodifluoroacetimidoyl chlorides with methyl ketones. beta-Bromodifluoromethyl beta-enammoketones smoothly cyclized to give a novel class of cyclic (2,2-difluoro-5-phenyl-furan-3-ylidene)-aryl-amines under basic condition. An intramolecular halophilic substitution mechanism was proposed. (c) 2005 Elsevier Ltd. All rights reserved.
ISSN:0040-4039
DOI:10.1016/j.tetlet.2005.06.002