Metal-Free Cascade 1,4-Conjugate Addition/Selective Annulation Strategy for Divergent Synthesis of Polysubstituted Imidazoles and 4-Alkenylquinazolines,Advanced Synthesis & Catalysis

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Metal-Free Cascade 1,4-Conjugate Addition/Selective Annulation Strategy for Divergent Synthesis of Polysubstituted Imidazoles and 4-Alkenylquinazolines
Advanced Synthesis & Catalysis ( IF 4.4 ) Pub Date : 2022-10-19 , DOI: 10.1002/adsc.202200905
Qiang Tang ₁ , Keke Xu ₁ , Xinwei He ₁ , Yongjia Shang ₁

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A metal-free cascade annulation of propagylamines with amidines for divergent synthesis of polysubstituted imidazoles and 4-alkenylquinazolines has been developed. The reaction is believed to proceed by sequential 1,4-conjugate addition of amidines to propargylamines, 5-exo-dig annulation/aromatization to form the polysubstituted imidazoles, and nucleophilic addition/elimination/aromatization to quinazoline skeleton. In this reaction, a broad range of electron-rich, electron-neutral, and electron-deficient propagylamines react well with amidines to give polysubstituted imidazoles and 4-alkenylquinazolines in 53–93% yields. Moreover, the utility of this method was showcased by gram-scale experiments and synthetic transformations of the product.

中文翻译：

多取代咪唑和 4-烯基喹唑啉的发散合成的无金属级联 1,4-共轭加成/选择性成环策略

已经开发了丙胺与脒的无金属级联环化，用于多取代咪唑和 4-烯基喹唑啉的发散合成。据信该反应是通过将脒顺序地 1,4-共轭加成到炔丙基胺、5-外环化/芳构化以形成多取代咪唑以及亲核加成/消除/芳构化到喹唑啉骨架来进行的。在该反应中，范围广泛的富电子、电子中性和缺电子丙胺与脒反应良好，以 53-93% 的收率生成多取代咪唑和 4-烯基喹唑啉。此外，该方法的效用已通过克级实验和产物的合成转化得到展示。

更新日期：2022-10-19

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