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Synthesis 2012; 44(22): 3477-3482
DOI: 10.1055/s-0032-1317383
DOI: 10.1055/s-0032-1317383
paper
Improved One-Pot Synthesis of 1-Aryl-3-trifluoroacetyl-1H-pyrroles under Swern Oxidation
Further Information
Publication History
Received: 10 July 2012
Accepted after revision: 18 September 2012
Publication Date:
02 October 2012 (online)
Abstract
This study describes an improved one-pot, four-step synthesis of a new series of 1-aryl-3-trifluoroacetyl pyrroles from the reaction of 3-trifluoroacetyl-4,5-dihydrofuran with arylamines, giving 1,1,1-trifluoro-3-(2-hydroxyethyl)-4-arylamino-3-buten-2-ones, which were directly submitted to Swern oxidation to furnish 1,1,1-trifluoro-3-(2-ethanal)-4-arylamino-3-buten-2-ones. Subsequent intramolecular cyclization of the corresponding enaminoaldehydes followed by aromatization rendered the title compounds in a 30 to 56% overall yield.
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