Sathyanarayana Balasubrahmanya K, Manjappa Kiran B, Yang Ding-Yah
Graduate Program for Biomedical and Materials Science, Tunghai University, Taiwan.
Department of Chemistry, Tunghai University, No. 1727, Sec. 4, Taiwan Boulevard, Xitun District, Taichung 407224, Taiwan.
Org Biomol Chem. 2023 Jul 26;21(29):5964-5969. doi: 10.1039/d3ob00917c.
A series of 2-aryl substituted chromeno[3,4-]pyrrol-4(3)-ones were prepared in two steps by employing 4-chloro-3-nitrocoumarin as a precursor. The reaction involved the base-mediated reductive coupling of 4-chloro-3-nitrocoumarin with α-bromoacetophenone, followed by reductive intramolecular cyclization to afford the pyrrolocoumarin ring. When α-bromoacetophenone was replaced with α-cyanoacetophenone, ()-4-(nitromethylene)-4-chromen-2-amine was isolated as the major product. The molecular structures of the prepared compounds were characterized by X-ray crystallography and the mechanisms for their formation were proposed.
以4-氯-3-硝基香豆素为前体，分两步制备了一系列2-芳基取代的色烯并[3,4-]吡咯-4(3)-酮。该反应包括4-氯-3-硝基香豆素与α-溴苯乙酮的碱介导还原偶联，随后进行还原分子内环化以得到吡咯并香豆素环。当α-溴苯乙酮被α-氰基苯乙酮取代时，分离得到() -4-(硝基亚甲基)-4-色烯-2-胺作为主要产物。通过X射线晶体学对所制备化合物的分子结构进行了表征，并提出了其形成机理。
