Oxidative Annulations Involving DMSO and Formamide: K2S2O8 Mediated Syntheses of Quinolines and Pyrimidines
Oxidative Annulations Involving DMSO and Formamide: K2S2O8 Mediated Syntheses of Quinolines and Pyrimidines
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DOI：
10.1021/acs.orglett.7b02838
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发表时间：
2017-10-20
期刊：
影响因子：
5.2
通讯作者：
Singh, Anand
中科院分区：
文献类型：
--
作者：
Jadhav, Santosh D.;Singh, Anand
描述了从容易获得的前体制备4-芳基喹啉和4-芳基嘧啶的有效策略。由K2 S2 O 8促进的氧化成环反应涉及苯胺、芳基酮和DMSO作为次甲基（=CH-）等价物，通过级联反应产生4-芳基喹啉，该级联反应需要产生硫离子、随后的C-N和C-C键形成和环化。还描述了该策略在活化苯乙酮甲酰胺缀合物合成4-芳基嘧啶中的应用。
An efficient strategy toward 4-arylquinolines and 4-arylpyrimidines from readily available precursors is described. Oxidative annulation promoted by K2S2O8 involving anilines, aryl ketones, and DMSO as a methine (=CH-) equivalent leads to 4-arylquinolines via a cascade that entails generation of a sulfenium ion, subsequent C-N and C-C bond formations, and cyclization. The application of this strategy to the activation of acetophenoneformamide conjugates toward the synthesis of 4-arylpyrimidines is also described.