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TBAI-mediated regioselective 5-exo-dig iodinative oxocyclization of 2-alkynylbenzamides for the synthesis of isobenzofuran-1-imines and isobenzofurans |
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| Authors: | Yan-Hua Wang Jin-Biao Liu Banlai Ouyang Hongwei Zhou Guanyinsheng Qiu |
| Institution: | 1. School of Metallurgical and Chemical Engineering, Jiangxi University of Science and Technology, 86 Hongqi Road, Ganzhou, 341000, China;2. College of Biological, Chemical Science and Engineering, Jiaxing University, 118 Jiahang Road, Jiaxing, 314001, China;3. Department of Chemistry, Nanchang Normal University, Nanchang, 330032, China |
| Abstract: | Alkyne-based regioselective functionalization is an important transformation method for the synthesis of a wide variety of organic products. In this work, a regioselective TBAI-mediated oxidative 5-exo-dig iodo-oxycyclization of 2-alkynylbenzamide is used for the synthesis of various isobenzofuran derivatives with excellent functional group tolerance and high reaction efficiency. We hypothesized that using water in a mixed solvent could change the reaction pathway and realize a high reaction regioselectivity. Furthermore, the application of the developed procedure was demonstrated by the synthesis of phthalazin-1(2H)-one and aryl-substituted isobenzofurans. |
| Keywords: | Isobenzofuran-1-imine Electrophilic iodocyclization Regioselective 2-alkynylbenzamide Tandem reaction |
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