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One-Pot Synthesis of Naphtho[1′,2′:4,5]imidazo[1,2-a ]pyridin-5-yl(aryl)methanones through Sequential Sonogashira Coupling/Alkyne-Carbonyl Metathesis
European Journal of Organic Chemistry ( IF 2.5 ) Pub Date : 2017-07-24 , DOI: 10.1002/ejoc.201700496
Mirza Feroz Baig 1, 2 , Siddiq Pasha Shaik 1, 2 , Namballa Hari Krishna 1, 3 , Neeraj Kumar Chouhan 1, 3 , Abdullah Alarifi 4 , Ahmed Kamal 1, 3, 4
Affiliation  

An efficient one-pot route for the construction of naphtho[1′,2′:4,5]imidazo[1,2-a]pyridin-5-yl(aryl)methanones and 5-phenylnaphtho[1′,2′:4,5]imidazo[1,2-a]pyridines by sequential Sonogashira coupling reaction followed by trifluoroacetic acid promoted alkyne-carbonyl metathesis (ACM) has been developed. 2-(2-Bromophenyl)imidazo[1,2-a]pyridine-3-carbaldehyde preferentially underwent ACM with phenyl acetylenes, whereas intramolecular hydroarylation reaction was the common pathway in the absence of a carbonyl moiety at the C-3 position under similar conditions. This protocol is compatible with a wide variety of functional groups and delivered corresponding naphtho[1′,2′:4,5]imidazo[1,2-a]pyridines in good to excellent yields.

中文翻译:

Naphtho[1',2':4,5]imidazo[1,2-a]pyridin-5-yl(aryl)methanones by Sequential Sonogashira Coupling/炔-羰基复分解一锅法合成

构建萘并[1',2':4,5]咪唑并[1,2-a]吡啶-5-基(芳基)甲酮和5-苯基萘并[1',2'的高效一锅法: 4,5]咪唑并[1,2-a]吡啶通过顺序Sonogashira偶联反应和三氟乙酸促进的炔-羰基复分解(ACM)得到了开发。2-(2-溴苯基)咪唑并[1,2-a]吡啶-3-甲醛优先与苯乙炔发生ACM,而分子内加氢芳基化反应是C-3位没有羰基部分的常见途径。使适应。该协议与多种官能团兼容,并提供相应的萘并 [1',2':4,5] 咪唑并 [1,2-a] 吡啶,收率良好至极好。
更新日期:2017-07-24
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