文献类型：期刊文献

英文题名：Orthogonal sp(3) C-1-H and N-H Bond Functionalization of 1,2,3,4-Tetrahydroisoquinolines via the Ugi Four-Component Reaction

作者：Yan, Ji-Min[1];Bai, Qi-Fan[1];Xu, Chang[1];Feng, Gaofeng[1]

机构：[1]Shaoxing Univ, Zhejiang Key Lab Alternat Technol Fine Chem Proc, Shaoxing 312000, Peoples R China

年份：2016

卷号：48

期号：21

起止页码：3730

外文期刊名：SYNTHESIS-STUTTGART

收录：SCI-EXPANDED(收录号：WOS:000386476600009)、、WOS、CCR-EXPANDED(收录号：WOS:000386476600009)

基金：Financial support from the National Natural Science Foundation of China (No. 21302130) and the Science Technology Department of Zhejiang Province (No. 2014C31141) is acknowledged with thanks. The authors also thank Dr. Tao Cai (Department of Chemistry, Xiamen University) for collection of the X-ray diffraction data. We also thank Professor Wei-Min Dai (Department of Chemistry, The Hong Kong University of Science and Technology) for discussions and help.

语种：英文

外文关键词：sp(3) C-H functionalization; Ugi reaction; redox-neutral reaction; 1; 2; 3; 4-tetrahydroisoquinolines; iminium isomerization

外文摘要：A new protocol for orthogonal sp(3) C-1-H and N-H bond functionalization of 1,2,3,4-tetrahydroisoquinolines has been established via the Ugi four-component reaction with aldehydes, isonitriles, and carboxylic acids. It was revealed that only the N-H bond could be functionalized when the reaction was performed in acetonitrile at room temperature; however, when the reaction was carried out in toluene at 80 degrees C, redox-neutral sp(3) C-1-H bond functionalization of 1,2,3,4-tetrahydroisoquinolines was achieved. Differing from the common role of carboxylic acid as a promoter in redox-neutral amine -functionalization, the carboxylic acid employed herein is also a reactant. The orthogonal process is compatible with various substrates and provides an appealing access to a library of structurally diverse 1,2,3,4-tetrahydroisoquinolines.