Department of Chemistry, Tsinghua University , Key Laboratory of Organic Optoelectronics & Molecular Engineering of Ministry of Education, Beijing 100084, China.
J Org Chem. 2012 Jul 6;77(13):5794-800. doi: 10.1021/jo3010414. Epub 2012 Jun 26.
An efficient one-pot synthesis of isoquinolines and heterocycle-fused pyridines by three-component reaction of aryl ketones, hydroxylamine, and alkynes is developed. The reaction involves condensation of aryl ketones and hydroxylamine, rhodium(III)-catalyzed C-H bond activation of the in situ generated aryl ketone oximes, and cyclization with internal alkynes. This protocol enables rapid assembly of multisubstituted isoquinolines as well as γ-carbolines, furo[2,3-c]pyridines, thieno[2,3-c]pyridines, and benzofuro[2,3-c]pyridines from readily available substrates.
开发了一种通过芳基酮、羟胺和炔烃的三组分反应高效合成异喹啉和杂环稠合吡啶的方法。该反应涉及芳基酮和羟胺的缩合、原位生成的芳酮肟的铑(III)催化 C-H 键活化以及与内部炔烃的环化。该方案能够从易得的底物快速组装多取代异喹啉以及γ-咔啉、呋喃[2,3-c]吡啶、噻吩[2,3-c]吡啶和苯并呋喃[2,3-c]吡啶。
