Synthesis ( IF 2.2 ) Pub Date : 2017-07-19 , DOI: 10.1055/s-0036-1588466 Jinsong Peng , Chunxia Chen , Deqiang Wang , Peng Sun , Peiyun Jia , Yixia Yue
Abstract
4-Quinolone and 4H-thiochromen-4-one derivatives are readily synthesized in a tandem one-pot manner in good to excellent yields. Starting from (Z)-β-chlorovinyl ketones, an intermolecular nucleophilic addition of amines or sodium hydrogen sulfide to (Z)-β-chlorovinyl ketones was followed by elimination of chlorine anion to give Z-enamine or thioenol intermediates, which can be transformed to 4-quinolone or 4H-thiochromen-4-one products through intramolecular SNAr reaction, respectively.
4-Quinolone and 4H-thiochromen-4-one derivatives are readily synthesized in a tandem one-pot manner in good to excellent yields. Starting from (Z)-β-chlorovinyl ketones, an intermolecular nucleophilic addition of amines or sodium hydrogen sulfide to (Z)-β-chlorovinyl ketones was followed by elimination of chlorine anion to give Z-enamine or thioenol intermediates, which can be transformed to 4-quinolone or 4H-thiochromen-4-one products through intramolecular SNAr reaction, respectively.
中文翻译:
![](https://scdn.x-mol.com/jcss/images/paperTranslation.png)
通过顺序亲核加成-消除-SNAr反应实现无过渡金属一锅串联合成4-喹诺酮和4H-硫代色素-4-酮衍生物
摘要
4-喹诺酮和4 H-硫代色素-4-酮衍生物很容易以串联-一锅方式以良好至极好的产率合成。从(Z)-β-氯乙烯酮开始,分子间亲核加成胺或硫化氢钠到(Z)-β-氯乙烯酮中,然后消除氯阴离子,得到Z-烯胺或硫代烯醇中间体,可以将其转化通过分子内的S N Ar反应分别生成4-喹诺酮或4 H-硫代色素-4-酮。
4-喹诺酮和4 H-硫代色素-4-酮衍生物很容易以串联-一锅方式以良好至极好的产率合成。从(Z)-β-氯乙烯酮开始,分子间亲核加成胺或硫化氢钠到(Z)-β-氯乙烯酮中,然后消除氯阴离子,得到Z-烯胺或硫代烯醇中间体,可以将其转化通过分子内的S N Ar反应分别生成4-喹诺酮或4 H-硫代色素-4-酮。