Silver(I)-Catalyzed Tandem Reaction of Enynones and 4-Alkenyl Isoxazoles: Synthesis of 2-(Furan-2-yl)-1,2-dihydropyridines,The Journal of Organic Chemistry

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Silver(I)-Catalyzed Tandem Reaction of Enynones and 4-Alkenyl Isoxazoles: Synthesis of 2-(Furan-2-yl)-1,2-dihydropyridines
The Journal of Organic Chemistry ( IF 3.3 ) Pub Date : 2023-05-15 , DOI: 10.1021/acs.joc.3c00312
Haiyun Peng _{1,

2} , Yangyi Zhang _{1,

2} , Guisheng Deng _{1,

2}

Affiliation

Silver(I)-catalyzed tandem reaction of enynones with 4-alkenyl isoxazoles provides access to 2-(furan-2-yl)-1,2-dihydropyridines. No competitive cyclopropanation of alkenes and O–H insertion via (2-furyl)carbene complexes were observed. The cascade reaction proceeds via the formation of (2-furyl)metal carbene intermediate, the N–O bond cleavage of 4-alkenyl isoxazoles/rearrangement, subsequent 6π electrocyclic reaction, and [1,5] H-shift. The successive construction of both 1,2-dihydropyridine skeleton and furan frame has been achieved in the one-pot reaction. A broad range of readily available enynones and 4-alkenyl isoxazoles are suitable to this protocol; however, when R³ is the alkyl group such as n-Bu and Me, a complicated mixture was generated without the desired products. In addition, in the case of R⁴ = bulky group such as R₃^′SiOCH₂, the reaction gave an in situ oxo-product of (2-furyl)silver carbene. An atom-economic strategy for the synthesis of 2-(furan-2-yl)-1,2-dihydropyridines has been established.

中文翻译：

银 (I) 催化烯酮和 4-烯基异恶唑的串联反应：2-(Furan-2-yl)-1,2-dihydropyridines 的合成

银 (I) 催化的烯酮与 4-烯基异恶唑的串联反应提供了获得 2-(furan-2-yl)-1,2-dihydropyridines 的途径。没有观察到烯烃的竞争性环丙烷化和通过（2-呋喃基）卡宾络合物的 O-H 插入。级联反应通过 (2-呋喃基) 金属卡宾中间体的形成、4-烯基异恶唑的 N-O 键断裂/重排、随后的 6π 电环反应和 [1,5] H 位移进行。通过一锅法反应实现了1,2-二氢吡啶骨架和呋喃骨架的连续构建。范围广泛的现成烯酮和 4-烯基异恶唑适用于该协议；然而，当R ³是烷基时，例如n-Bu 和 Me，生成了复杂的混合物，没有所需的产物。此外，在 R ⁴ = 大基团（例如 R ₃^' SiOCH _{2 ）}的情况下，反应产生（2-呋喃基）银卡宾的原位氧代产物。已经建立了用于合成 2-(furan-2-yl)-1,2-dihydropyridines 的原子经济策略。

更新日期：2023-05-15

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