Synthesis 2012; 44(22): 3477-3482
DOI: 10.1055/s-0032-1317383
paper
© Georg Thieme Verlag Stuttgart · New York

Improved One-Pot Synthesis of 1-Aryl-3-trifluoroacetyl-1H-pyrroles under Swern Oxidation

Nilo Zanatta*
Núcleo de Química de Heterociclos (NUQUIMHE), Departamento de Química, Universidade Federal de Santa Maria, 97105-900, Santa Maria, Brazil   Fax: +55(55)32208756   Email: zanatta@base.ufsm.br
,
Estefania da C. Aquino
Núcleo de Química de Heterociclos (NUQUIMHE), Departamento de Química, Universidade Federal de Santa Maria, 97105-900, Santa Maria, Brazil   Fax: +55(55)32208756   Email: zanatta@base.ufsm.br
,
Fabio M. da Silva
Núcleo de Química de Heterociclos (NUQUIMHE), Departamento de Química, Universidade Federal de Santa Maria, 97105-900, Santa Maria, Brazil   Fax: +55(55)32208756   Email: zanatta@base.ufsm.br
,
Helio G. Bonacorso
Núcleo de Química de Heterociclos (NUQUIMHE), Departamento de Química, Universidade Federal de Santa Maria, 97105-900, Santa Maria, Brazil   Fax: +55(55)32208756   Email: zanatta@base.ufsm.br
,
Marcos A. P. Martins
Núcleo de Química de Heterociclos (NUQUIMHE), Departamento de Química, Universidade Federal de Santa Maria, 97105-900, Santa Maria, Brazil   Fax: +55(55)32208756   Email: zanatta@base.ufsm.br
› Author Affiliations
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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