Synthesis of Indeno[1′,2′:4,5]imidazo[1,2-a]pyridin-11-ones and Chromeno[4′,3′:4,5]imidazo[1,2-a]pyridin-6-ones through Palladium-Catalyzed Cascade Reactions of 2-(2-Bromophenyl)imidazo[1,2-a]pyridines,The Journal of Organic Chemistry

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Synthesis of Indeno[1′,2′:4,5]imidazo[1,2-a]pyridin-11-ones and Chromeno[4′,3′:4,5]imidazo[1,2-a]pyridin-6-ones through Palladium-Catalyzed Cascade Reactions of 2-(2-Bromophenyl)imidazo[1,2-a]pyridines
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2016-03-29 00:00:00 , DOI: 10.1021/acs.joc.6b00166
Ju Zhang ₁ , Xinying Zhang ₁ , Xuesen Fan ₁

Affiliation

A novel and efficient synthesis of 11H-indeno[1′,2′:4,5]imidazo[1,2-a]pyridin-11-one, a hybrid structure of indenone with imidazo[1,2-a]pyridine, from the reaction of 2-(2-bromophenyl)imidazo[1,2-a]pyridine with carbon monoxide through palladium-catalyzed CO insertion and C–H bond activation, has been developed. Intriguingly, under similar conditions but in the presence of Cu(OAc)₂, the reaction selectively afforded 6H-chromeno[4′,3′:4,5]imidazo[1,2-a]pyridin-6-one, a hybrid structure of chromenone with imidazo[1,2-a]pyridine, via a more sophisticated cascade process including acetoxylation, deacetylation, CO insertion, and C–H bond activation.

中文翻译：

茚并的合成[1'，2'：4,5]咪唑并[1,2一]吡啶11酮和色烯并[4'，3'：4,5]咪唑并[1,2一]吡啶2-（2-溴苯基）咪唑并[1,2- a ]吡啶的钯催化级联反应形成6-ones

新型高效合成11 H-茚并[1'，2'：4,5]咪唑并[1,2 - a ]吡啶-11-酮，茚满酮与咪唑并[1,2- a ]吡啶的杂化结构通过2-（2-溴苯基）咪唑并[1,2- a ]吡啶与一氧化碳的反应，通过钯催化的CO插入和CH键的活化，已经得到了发展。有趣的是，在相似的条件下但在Cu（OAc）₂的存在下，反应选择性地提供了6 H -chromeno [4'，3'：4,5]咪唑并[1,2 - a ]吡啶-6-one，a色酮与咪唑[1,2- a]的杂化结构吡啶，通过更复杂的级联过程，包括乙酰氧基化，脱乙酰化，CO插入和C–H键激活。

更新日期：2016-03-29

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