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.
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页数：16
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