Access to Functionalized 3H-Pyrrolo[2,3-c]quinolin-4(5H)-ones and Thieno[2,3-c]quinolin-4(5H)-ones via Domino Reaction of 4-Alkynyl-3-bromoquinolin-2(1H)-ones

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• 作者：Zhiyong Wang ; Lijun Xue ; Yiyi He ; Licong Weng ; Ling Fang
• 刊名：Journal of Organic Chemistry
• 出版年：2014
• 出版时间：October 17, 2014
• 年：2014
• 卷：79
• 期：20
• 页码：9628-9638
• 全文大小：484K
• ISSN：1520-6904

文摘

We describe two efficient protocols for the straightforward synthesis of 3H-pyrrolo[2,3-c]quinolin-4(5H)-one and thieno[2,3-c]quinolin-4(5H)-one derivatives from readily available 4-alkynyl-3-bromoquinolin-2(1H)-one as precursor. The efficient synthesis of highly functionalized 3H-pyrrolo[2,3-c]quinolin-4(5H)-ones has been achieved via a palladium-catalyzed domino reaction of 4-alkynyl-3-bromoquinolin-2(1H)-ones with amines. Thieno[2,3-c]quinolin-4(5H)-one derivatives were also conveniently synthesized via sequential nucleophilic aromatic substitution/5-endo-dig cyclization between 4-alkynyl-3-bromoquinolin-2(1H)-ones and sodium sulfide with good functional tolerance under mild conditions.