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Synthesis of naphtho[1′,2′:4,5]imidazo[1,2-a]pyridines via Rh(III)-catalyzed C–H functionalization of 2-arylimidazo[1,2-a]pyridines with cyclic 2-diazo-1,3-diketones featuring with a ring opening and reannulation
Organic Chemistry Frontiers ( IF 5.4 ) Pub Date : 2020-02-26 , DOI: 10.1039/d0qo00073f
Bin Li 1, 2, 3, 4, 5 , Nana Shen 1, 2, 3, 4, 5 , Yujie Yang 1, 2, 3, 4, 5 , Xinying Zhang 1, 2, 3, 4, 5 , Xuesen Fan 1, 2, 3, 4, 5
Affiliation  

An unprecedented synthesis of functionalized naphtho[1′,2′:4,5]imidazo[1,2-a]pyridines via rhodium-catalyzed cascade reactions of 2-arylimidazo[1,2-a]pyridine-3-carbaldehydes with cyclic α-diazo-1,3-diketones is presented. To our knowledge, this is the first example in which the title compounds were prepared through Rh(III)-catalyzed C–H bond carbenoid insertion and [5 + 1] annulation by using cyclic α-diazo-1,3-diketones as a C1 synthons featuring with a ring-opening and reannulation. Notably, a wide range of substrates and functional groups were well-tolerated under the optimized reaction conditions to produce products in good to excellent yields.

中文翻译:

通过Rh(III)催化2-芳基咪唑并[1,2-a]吡啶与环2-的合成反应合成萘并[1',2':4,5]咪唑并[1,2-a]吡啶重氮-1,3-二酮,具有开环和重新环化的特征

官能化萘的合成前所未有[1',2':4,5]咪唑并[1,2]吡啶通过铑催化的2芳基咪唑并[1,2的级联反应]吡啶-3- carbaldehydes与环状提出了α-重氮-1,3-二酮。据我们所知,这是第一个实例,其中标题化合物是通过Rh(III)催化的C–H键类固醇插入并通过使用环状α-重氮-1,3-二酮作为[5 +1]环化制备的。 C1合成子具有开环和重新环化的特征。值得注意的是,在优化的反应条件下,广泛的底物和官能团具有良好的耐受性,可生产出具有良好收率的产品。
更新日期:2020-02-26
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