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Synthesis of Polyfluorinated Nitrogen‐Containing Heterocycles from Hemifluorinated Enones or Organofluorosilicon Building Blocks as Synthetic Equivalents
Author(s) -
Chanteau Frédéric,
Didier Benoît,
Dondy Boniface,
Doussot Pascale,
PlantierRoyon Richard,
Portella Charles
Publication year - 2004
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200300671
Subject(s) - chemistry , vicinal , reagent , nucleophile , fluorine , nitrogen atom , organic chemistry , nitrogen , combinatorial chemistry , group (periodic table) , catalysis
Abstract A series of polyfluorinated heterocycles has been prepared by heterocyclisation of hemifluorinated enones or organofluorosilicon synthetic equivalents with different bis(nucleophiles). These polyfluorinated building blocks were obtained by treatment of acylsilanes with perfluoro organometallic reagents. The method is general and has been applied to aliphatic, aromatic and carbohydrate derivatives, to give oxazolidines, imidazolidines, benzodia‐ and ‐thiazepines, quinolines and pyrimidines bearing both a fluorine atom and a perfluoroalkyl group in vicinal positions. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2004)