化学
亚甲基
氧化还原
亲核细胞
腈
硫黄
组合化学
废止
缩合反应
Knoevenagel冷凝
亲核加成
有机化学
催化作用
作者
Peiyun Jiang,Bingwei Hu,Yuan Xu,Jimei Yang,Xingjiang Yang,Jun Lin,Yi Jin
标识
DOI:10.1021/acs.joc.2c01882
摘要
Herein, we report an elemental sulfur-promoted switchable redox condensation reaction that can selectively prepare 2-aminofurans and 2-aminothiophenes from the corresponding enaminones and methylene nitriles, respectively. Mechanistic studies demonstrated that the enaminones, as dual nucleophiles, reacted with nitrile acetate to produce 2-aminofurans via 3,5-annulation under promotion by elemental sulfur. These reactions used readily available starting materials, transition metal-free, eco-friendly procedures, gram-scale syntheses, and wide functional group tolerance. The methodology may be useful for the construction of 2-aminofuran and 2-aminothiophene derivatives with potential biological activity.
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