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

文献情報

出版日 2020-02-26

DOI 10.1039/D0QO00073F

インパクトファクター 5.281

著者

Bin Li, Nana Shen, Yujie Yang, Xinying Zhang, Xuesen Fan

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要旨

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.

掲載誌

Organic Chemistry Frontiers

CiteScore: 7.8

自己引用率: 8.7%

年間論文数: 724

Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry

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

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