Chinese Journal of Organic Chemistry >
New Method for Synthesis of 3-Arylindolizines from Electron-Deficient Alkynes through 1, 3-Dipolar Cycloaddition
Received date: 2014-01-03
Revised date: 2014-01-26
Online published: 2014-02-12
Supported by
Project supported by the National Natural Science Foundation of China (No. 21202058), the Natural Science Foundation of Jiangsu Province (No. BK2011408), and the Department of Education of Jiangsu Province (No. 13KJA150001).
A novel and efficient procedure for the preparation of 3-aryl-indolizine by 1,3-dipolar cycloaddition was established. The pyridinium salts were prepared from the corresponding pyridines and benzyl halides. In the presence of cesium carbonate, electron-deficient alkynes reacted with the pyridinium salts in 1,4-dioxane through 1,3-dipolar cycloaddition followed by an aromatization reaction to generate the corresponding 3-aryl-indolizines. This method features cheap reagents, a simple workup procedure, mild conditions, high regioselectivity and generating the desired products in moderate to high yield (34%～81%).
Key words： indolizine; 1,3-dipolar cycloaddition; electron-deficient alkyne
Li Guodong , Hu Huayou , Kan Yuhe , Ma Kuirong . New Method for Synthesis of 3-Arylindolizines from Electron-Deficient Alkynes through 1, 3-Dipolar Cycloaddition[J]. Chinese Journal of Organic Chemistry, 2014 , 34(5) : 903 -908 . DOI: 10.6023/cjoc201401001
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