铑乙烯基卡宾与氨基查耳酮的意外串联反应用于合成功能化喹啉。
A serendipitous cascade of rhodium vinylcarbenoids with aminochalcones for the synthesis of functionalized quinolines.
作者信息
Chinthapally Kiran, Massaro Nicholas P, Padgett Haylee L, Sharma Indrajeet
机构信息
Department of Chemistry and Biochemistry, and Institute of Natural Products Applications and Research Technologies, University of Oklahoma, 101 Stephenson Parkway, Norman, OK-73071, USA.
出版信息
Chem Commun (Camb). 2017 Nov 9;53(90):12205-12208. doi: 10.1039/c7cc07181g.
A serendipitous five-step cascade of rhodium vinylcarbenoids with aminochalcones enables a unique synthetic approach to highly functionalized tri- and tetra-cyclic quinolines. The cascade reaction begins with the insertion of aminochalcone nitrogen into rhodium vinylcarbenoids followed by intramolecular aldol cyclization to provide a substituted indoline intermediate that undergoes an oxy-Cope rearrangement to provide a 9-membered azacycle, which then rearranges to the functionalized quinoline through an intramolecular aldol/dehydration sequence. With a catalyst loading as low as 0.1 mol%, the cascade reaction has proven to be general with a range of aminochalcones and vinylcarbenoids.
铑乙烯基卡宾与氨基查耳酮的五步串联反应意外地为高官能化的三环和四环喹啉提供了一种独特的合成方法。该串联反应始于氨基查耳酮氮插入铑乙烯基卡宾中，随后进行分子内羟醛环化反应，生成取代吲哚啉中间体，该中间体再经过氧杂-Cope重排生成九元氮杂环，然后通过分子内羟醛/脱水序列重排为官能化喹啉。该串联反应的催化剂负载量低至0.1 mol%，已证明对一系列氨基查耳酮和乙烯基卡宾具有通用性。
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