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

被引：5
作者：
Zanatta, Nilo [1 ]
Aquino, Estefania da C. [1 ]
da Silva, Fabio M. [1 ]
Bonacorso, Helio G. [1 ]
Martins, Marcos A. P. [1 ]
机构：
[1] Univ Fed Santa Maria, Dept Quim, Nucleo Quim Heterociclos NUQUIMHE, BR-97105900 Santa Maria, RS, Brazil
来源：
SYNTHESIS-STUTTGART | 2012年 / 44卷 / 22期
关键词：
trifloroacetyl groups; pyrroles; Swern oxidation; arylamines; trifluoromethyl; CATALYZED N-ARYLATION; POLYSUBSTITUTED PYRROLES; DIMETHYL-SULFOXIDE; MEDIATED SYNTHESIS; CONVENIENT METHOD; EFFICIENT; ALCOHOLS; DERIVATIVES; ENTRY; DIMETHYLSULFOXIDE;
D O I：
10.1055/s-0032-1317383
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
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-2ones, 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.
引用
收藏
页码：3477 / 3482
页数：6
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