Palladium-Catalyzed Sonogashira-Coupling Conjoined C鈥揌 Activation: A Regioselective Tandem Strategy to Access Indolo- and Pyrrolo[1,2-a]quinolines

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• 作者：Satya Prakash Shukla ; Rakesh K. Tiwari ; Akhilesh K. Verma
• 刊名：The Journal of Organic Chemistry
• 出版年：2012
• 出版时间：November 16, 2012
• 年：2012
• 卷：77
• 期：22
• 页码：10382-10392
• 全文大小：479K
• 年卷期：v.77,no.22(November 16, 2012)
• ISSN：1520-6904

文摘

An operationally simple approach for the regioselective tandem synthesis of indolo[1,2-a]quinolines 4a鈥?b>v and pyrrolo[1,2-a]quinolines 5a鈥?b>k from 1-(2-bromophenyl)-1H-indole/pyrrole/imidazole 1a鈥?b>c, 2a,b by the palladium-catalyzed sequential C鈥揅 bond formation is described. The developed approach involves the palladium-catalyzed Sonogashira coupling followed by the intramolecular C鈥揅 bond formation via C鈥揌 activation, which leads to the formation of 6-endo-dig cyclized product. This synthetic methodology accommodates wide functional group variation on alkyne, which proves to be advantageous for the structural and biological activity assessments.