Hexafluoroisopropanol as solvent and promotor in the Paal-Knorr synthesis of N-substituted diaryl pyrroles

被引：10

作者：

Schirmacher, Robert H. E. ^{[3
,4
]}

Roesch, Daniel ^{[3
,4
]}

Thomas, Franziska ^{[1
,2
,3
,4
]}

机构：

[1] Heidelberg Univ, Inst Organ Chem, Neuenheimer Feld 270, D-69120 Heidelberg, Germany

[2] Ctr Adv Mat, Neuenheimer Feld 270, D-69120 Heidelberg, Germany

[3] Georg August Univ, Inst Organ & Biomol Chem, Tammanstr 2, D-37077 Gottingen, Germany

[4] Ctr Biostruct Imaging Neurodegenerat, Von Siebold Str 3a, D-37075 Gottingen, Germany

来源：

TETRAHEDRON | 2021年 / 83卷

关键词：

Fluorinated solvents; Heterocycles; Pyrroles; Paal-knorr synthesis;

D O I：

10.1016/j.tet.2021.131985

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An additive-free synthesis of challenging N-substituted aryl pyrroles from the often poorly soluble corresponding 1,4-diketones by means of the Paal-Knorr pyrrole synthesis is reported, which makes use of the unique properties of 1,1,1,3,3,3-hexafluoroisopropanol (HFIP) as a solvent and reaction promotor. Our procedure offers simple execution and purification as well as easy scale-up and can be applied in the Paal-Knorr synthesis of a large number of structurally diverse pyrroles including the synthetically challenging tetra- and penta-substituted pyrroles in moderate to excellent yields. HFIP can also be used as solvent in the Paal-Knorr synthesis of furans and thiophenes; however, the solvent effect is more pronounced in synthesis of pyrroles. (C) 2021 Elsevier Ltd. All rights reserved.

引用

页数：16

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