Novel 3-acetyl-2-methyl-polyfluorochromones in reactions with amines and esters of amino acids

被引:5
|
作者
Shcherbakov, Konstantin V. [1 ]
Bazhin, Denis N. [1 ]
Burgart, Yanina V. [1 ]
Saloutin, Victor I. [1 ]
机构
[1] Russian Acad Sci, Ural Branch, I Ya Postovskii Inst Organ Synth, 22 S Kovalevskoi St,20 Akad Skaya St, Ekaterinburg 620990, Russia
关键词
amine; chromone; acylation; deacylation; ring opening; N-NUCLEOPHILES; METAL-COMPLEXES; ANTIBACTERIAL AGENTS; MEDICINAL CHEMISTRY; COPPER(II) CHELATE; PROMOTED SYNTHESIS; DERIVATIVES; BENZOPYRANS; 5,6,7,8-TETRAFLUOROCHROMONES; TRANSFORMATIONS;
D O I
10.1007/s10593-016-1805-y
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Novel 3-acetyl-2-methyl-polyfluoro-4De-chromen-4-ones were obtained via one-pot acylation of acetylacetone with polyfluorobenzoyl chlorides. These chromones were shown to form N-substituted 3-amino-1-[2-hydroxy(polyfluoro)phenyl]but-2-en-1-ones in reaction with aliphatic primary amines, esters of amino acids, and aqueous ammonia via opening of the pyrone ring and deacylation.
引用
收藏
页码:961 / 968
页数:8
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