3-(3,4-Dihydroxyphenyl)-8-hydroxy-2H-chromen-2-one

被引:0
|
作者
Svinyarov, Ivan [1 ]
Bogdanov, Milen [1 ]
机构
[1] Univ Sofia St Kl Ohridski, Fac Chem & Pharm, 1 James Bourchier Blvd, Sofia 1164, Bulgaria
关键词
polyhydroxylated; 3-arylcoumarins; 3,4-dihydroisocoumarin; domino reaction;
D O I
10.3390/M870
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
We report a novel protocol for the synthesis of 3-(3,4-dihydroxyphenyl)-8hydroxy-2H-chromen-2-one via demethylation/delactonization/elimination/lactonization/decarboxylation domino reaction sequence of diastereomeric mixture of cis-and trans-3(2,3-dimethoxyphenyl)-6,7-dimethoxy-1-oxoisochroman-4-carboxylic acids in boiling HBr/AcOH. The structure of the target compound was established for the first time by means of spectral methods such as H-1-, C-13-, DEPT-135-NMR, IR and HRMS.
引用
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页数:5
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