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Synthesis 2005(8): 1269-1278
DOI: 10.1055/s-2005-865290
DOI: 10.1055/s-2005-865290
PAPER
© Georg Thieme Verlag Stuttgart · New YorkA Convenient Synthesis and Chemical Properties of 3-Acylamino-6-polyfluoroalkyl-2H-pyran-2-ones
Further Information
Received
10 November 2004
Publication Date:
07 April 2005 (online)
Publication History
Publication Date:
07 April 2005 (online)
Abstract
A number of 3-acylamino-6-polyfluoroalkyl-2H-pyran-2-ones 3 were synthesized from β-alkoxyvinyl polyfluoroalkyl ketones 1 and N-acylglycines 2 in acetic anhydride in high yield. The reactions of trifluoromethyl-containing 2H-pyran-2-one 3b with O- and N-nucleophiles were studied and 3-N-benzoylamino-6-hydroxy-6-trifluoromethyl-5,6-dihydro-2H-pyran-2-one (13), 3-N-benzoylamino-6-hydroxy-6-trifluoromethyl-5,6-dihydro-2H-pyridin-2-one (14a), and N- and O-substituted 3-(N-benzoylamino)-6-trifluoromethyl-2H-pyridin-2-ones (15c,e, and 16) were synthesized.
Key words
enones - heterocycles - 2H-pyran-2-ones - 2H-pyridin-2-ones - aminations - alkylations - trifluoromethyl
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