Microwave-assisted three-component coupling-addition-SNAr (CASNAR) sequences to annelated 4H-thiopyran-4-ones

被引：39
|
作者：
Willy, Benjamin [1 ]
Frank, Walter [2 ]
Mueller, Thomas J. J. [1 ]
机构：
[1] Univ Dusseldorf, Inst Organ Chem & Makromol Chem, D-40225 Dusseldorf, Germany
[2] Univ Dusseldorf, Lehrstuhl Anorgan Chem & Strukturchem, D-40225 Dusseldorf, Germany
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2010年 / 8卷 / 01期
关键词：
MULTICOMPONENT SYNTHESES; CATALYZED GENERATION; 4H-1-BENZOTHIOPYRAN-4-ONES; DERIVATIVES; THIOFLAVONES; HETEROCYCLES; SODIUM;
D O I：
10.1039/b917627f
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A whole family of annelated 4H-thiopyran-4-ones as the core structural unit was readily synthesized in good yields by a microwave-assisted coupling-addition-SNAr (CASNAR) sequence starting from readily available (het) aroyl chlorides, alkynes and sodium sulfide nonahydrate in a consecutive one-pot three-component reaction. All representatives display a pronounced halochromicity of the absorption bands upon protonation. According to DFT calculations, the electronic ground state of the annelated 4H-thiopyran-4-ones possess a considerable zwitterionic character.
引用
收藏
页码：90 / 95
页数：6
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