FeCl3•6H2O-Catalyzed Intermolecular-Cascade Cyclization of Acetoacetanilide: Aldehyde-Tuned Synthesis to Valuable 2-Pyridone Analogues

被引：54

作者：

Sengupta, Tista ^{[1
]}

Gayen, Krishnanka S. ^{[1
]}

Pandit, Palash ^{[1
]}

Maiti, Dilip K. ^{[1
]}

机构：

[1] Univ Calcutta, Dept Chem, Univ Coll Sci, Kolkata 700009, India

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2012年 / 18卷 / 07期

关键词：

2-pyridone; cyclization; iron; regioselectivity; stereoselectivity; H BOND ACTIVATION; EFFICIENT SYNTHESIS; PART I; DERIVATIVES; INHIBITORS; CYCLOADDITION; CYANOACETAMIDE; PYRIDINES; CHEMISTRY; MECHANISM;

D O I：

10.1002/chem.201103354

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The first ever breakthrough toward activation of β-ketoacetanilide and subsequent C-C and C-N bond-forming intermolecular-cascade cyclization processes is demonstrated by development of the unprecedented Lewis acid property of non-toxic FeCl 3·6H 2O. Aromatic, aliphatic, α,β-unsaturated, chiral sugar-based and chromone aldehydes were regio- and stereoselectively cyclized with acetoacetanilides toward construction of valuable N-containing highly functionalized 2-pyridones (see scheme for an example). © 2012 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

引用

页码：1905 / 1909

页数：5

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