Tandem (2+2) Annulation/Retro-4 pi Electrocyclization/Imino-Nazarov Cyclization Reaction of p-Quinone Methides with Ynamides: Expeditious Construction of Functionalized Aminoindenes
Tandem (2+2) Annulation/Retro-4 pi Electrocyclization/Imino-Nazarov Cyclization Reaction of p-Quinone Methides with Ynamides: Expeditious Construction of Functionalized Aminoindenes
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对醌甲基化物与酰胺的串联 (2 2) 成环/Retro-4 pi 电环化/亚氨基-纳扎罗夫环化反应：快速构建功能化氨基茚
DOI：
10.1021/acs.orglett.1c02003
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发表时间：
2021
期刊：
影响因子：
5.2
通讯作者：
Fan Chun-An
中科院分区：
文献类型：
--
作者：
Yu Ke-Yin;Deng Yu-Hua;Ge Xiao-Min;An Xian-Tao;Shu Peng-Fei;Cao Ye-Xing;Zhao Xian-He;Fan Chun-An
描述了对醌甲基化物（p-QM）与炔酰胺的新串联环化。该级联反应具有 (2 + 2) 环化、逆 4π 电环化和亚氨基-纳扎罗夫环化的独特组合，其中乙烯基对醌甲基化物 (p-VQM) 作为关键中间体之一已被化学鉴定。值得注意的是，p-QM 的不寻常结构重建涉及 C5-C6 键的裂解和 C4-C6 键的后期形成，从而导致了构建功能化氨基茚的方法学的发展。
A new tandem annulation ofp-quinone methides (p-QMs) with ynamides is described. This cascade reaction features a unique combination of (2 + 2) annulation, retro-4π electrocyclization, and imino-Nazarov cyclization, wherein vinylp-quinone methides (p-VQMs) as one of the key intermediates have been identified chemically. Significantly, an unusual structural reconstruction ofp-QMs involving the cleavage of the C5–C6 bond and the late-stage formation of the C4–C6 bond is involved, leading to a methodology development for the construction of functionalized aminoindenes.