4-Chloro-3-(trifluoroacetyl)- and 4-chloro-3-(methoxalyl)coumarins as novel and efficient building blocks for the regioselective synthesis of 3,4-fused coumarins

被引:45
作者
Iaroshenko, Viktor O. [1 ,2 ]
Erben, Friedrich [1 ]
Mkrtchyan, Satenik [1 ,3 ]
Hakobyan, Ani [1 ,3 ]
Vilches-Herrera, Marcelo [1 ]
Dudkin, Sergii [1 ]
Bunescu, Alina [1 ,5 ]
Villinger, Alexander [1 ]
Sosnovskikh, Vyacheslav Ya [4 ]
Langer, Peter [1 ,5 ]
机构
[1] Univ Rostock, Inst Chem, D-18059 Rostock, Germany
[2] Natl Taras Shevchenko Univ, UA-01033 Kiev, Ukraine
[3] Yerevan State Univ, Fac Chem, Yerevan 0025, Armenia
[4] Ural State Univ, Dept Chem, Ekaterinburg 620083, Russia
[5] Univ Rostock eV, Leibniz Inst Katalyse, D-18059 Rostock, Germany
关键词
Coumarins; Heterocyclisation; Dinucleophiles; Heterocycles; Regioselectivity; NICOTINIC-ACID DERIVATIVES; DIELS-ALDER REACTION; 3-SUBSTITUTED COUMARINS; ACTIVE METHYLENE; FACILE SYNTHESIS; PRIMARY AMINES; RING-CLOSURE; 3-(POLYFLUOROACYL)CHROMONES; CHEMISTRY; ADDUCTS;
D O I
10.1016/j.tet.2011.08.030
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
4-Chloro-3-(trifluoroacetyl)- and 4-chloro-3-(methoxalyl)coumarins react with electron-rich aminoheterocycles, dimethyl 1,3-acetonedicarboxylate, hydrazines, alkyl thioglycolates, and methyl sarcosinate to give a variety of 3,4-heteroannulated coumarins. The starting materials were prepared by the reaction of 4-hydroxycoumarin with trifluoroacetic anhydride and methyl 2-chloro-2-oxoacetate in the presence of trimethylsilylchloride. An NMR study and X-ray crystallographic analysis are reported. (C) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码:7946 / 7955
页数:10
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