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
Literature Information
Publication Date
2020-02-26
DOI
10.1039/D0QO00073F
Impact Factor
5.281
Authors
Bin Li, Nana Shen, Yujie Yang, Xinying Zhang, Xuesen Fan
View Original
Abstract
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.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
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
Recommended Compounds
![N-[(1S,2R,4S)-2-Amino-4-(dimethylcarbamoyl)cyclohexyl]-N'-(5-chloro-2-pyridinyl)ethanediamide structure](https://static.chemtradehub.com/structs/480/480452-37-7-0898.webp "N-[(1S,2R,4S)-2-Amino-4-(dimethylcarbamoyl)cyclohexyl]-N'-(5-chloro-2-pyridinyl)ethanediamide structure")
N-[(1S,2R,4S)-2-Amino-4-(dimethylcarbamoyl)cyclohexyl]-N'-(5-chloro-2-pyridinyl)ethanediamide
CAS Number:
480452-37-7
Molecular Formula:
C16H22ClN5O3
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