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Issue 7, 2020
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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

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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.

Graphical abstract: 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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Article information


Submitted
16 Jan 2020
Accepted
25 Feb 2020
First published
26 Feb 2020

Org. Chem. Front., 2020,7, 919-925
Article type
Research Article

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

B. Li, N. Shen, Y. Yang, X. Zhang and X. Fan, Org. Chem. Front., 2020, 7, 919
DOI: 10.1039/D0QO00073F

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