One-pot and divergent synthesis of polysubstituted quinolin-2(1H)-ones and oxireno[2,3-c]quinolin-2(1aH,3H,7bH)-ones via sequential Ugi/Knoevenagel condensation/hydrolysis and Ugi/Corey–Chaykovsky epoxidation reactions,Organic Chemistry Frontiers

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One-pot and divergent synthesis of polysubstituted quinolin-2(1H)-ones and oxireno[2,3-c]quinolin-2(1aH,3H,7bH)-ones via sequential Ugi/Knoevenagel condensation/hydrolysis and Ugi/Corey–Chaykovsky epoxidation reactions
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2022-09-16 , DOI: 10.1039/d2qo01130a
Mao-Lin Yang ₁ , Hong-Ling Pan ₁ , Han-Han Kong ₁ , Ming-Wu Ding ₁

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A new one-pot and divergent synthesis of multisubstituted quinolin-2(1H)-ones and oxireno[2,3-c]quinolin-2(1aH,3H,7bH)-ones via sequential Ugi/Knoevenagel condensation/hydrolysis and Ugi/Corey–Chaykovsky epoxidation reactions was developed. The four-component reactions of 2-acylanilines, aldehydes, (carboxymethyl)(dimethyl)sulfonium bromides and isocyanides gave Ugi adducts, which were subsequently treated with DBU to produce polysubstituted quinolin-2(1H)-ones or oxireno[2,3-c]quinolin-2(1aH,3H,7bH)-ones in good overall yields by intramolecular Knoevenagel condensation/hydrolysis or intramolecular Corey–Chaykovsky epoxidation reactions.

中文翻译：

通过顺序 Ugi/Knoevenagel 缩合/水解和 Ugi/Corey 的多取代 quinolin-2(1H)-ones 和 oxireno[2,3-c]quinolin-2(1aH,3H,7bH)-ones 的一锅法和发散合成-柴可夫斯基环氧化反应

多取代 quinolin-2(1 H )-ones 和 oxireno[2,3 - c ]quinolin-2(1a H ,3 H ,7b H ) -ones的新一锅法和发散合成方法开发了水解和 Ugi/Corey-Chaykovsky 环氧化反应。2-酰基苯胺、醛、（羧甲基）（二甲基）溴化锍和异氰化物的四组分反应生成 Ugi 加合物，随后用 DBU 处理生成多取代的 quinolin-2(1 H )-ones 或 oxireno[2,3 - c ]quinolin-2(1a H ,3 H ,7b H)-通过分子内 Knoevenagel 缩合/水解或分子内 Corey-Chaykovsky 环氧化反应获得良好的总产率。

更新日期：2022-09-16

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