Synthesis of chromones and 4-hydroxyquinolines based on uncatalyzed condensations of 1-methoxy-1,3-bis(trimethylsilyloxy)-1,3-butadiene with 2-alkoxy- and 2-nitrobenzoyl chlorides and related reactions

被引：11
|
作者：
Rahn, Thomas [1 ,2 ]
Appel, Bettina [1 ]
Baumann, Wolfgang [2 ]
Jiao, Haijun [2 ]
Boerner, Armin [1 ,2 ]
Fischer, Christine [2 ]
Langer, Peter [1 ,2 ]
机构：
[1] Univ Rostock, Inst Chem, D-18059 Rostock, Germany
[2] Univ Rostock, Leibniz Inst Katalyse eV, D-18059 Rostock, Germany
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2009年 / 7卷 / 09期
关键词：
REGIOSELECTIVE SYNTHESIS; CYCLIZATION REACTIONS; ACID-CHLORIDES; ACYLATION; 1,3-BIS(TRIMETHYLSILYLOXY)-1,3-BUTADIENES; BIOSYNTHESIS; DERIVATIVES;
D O I：
10.1039/b901092k
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The reaction of 1-methoxy-1,3-bis(trimethylsilyloxy)-1,3-butadiene with 2-methoxybenzoyl chlorides afforded 3,5-diketoesters which were transformed, by treatment with boron tribromide, into functionalized 2-hydroxychroman-4-ones or chromones. The reaction of 1-methoxy-1,3-bis(trimethylsilyloxy)-1,3-butadiene with 2-nitrobenzoyl chlorides and subsequent reduction of the nitro group afforded functionalized 4-hydroxyquinolines. Their tautomeric equilibrium was studied by NMR spectroscopy and by computational methods.
引用
收藏
页码：1931 / 1938
页数：8
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