文献类型：期刊文献

英文题名：Efficient and Practical One-Pot Conversions of N-Tosyltetrahydroisoquinolines into Isoquinolines and of N-Tosyltetrahydro-β-carbolines into β-Carbolines through Tandem β-Elimination and Aromatization

作者：Dong, Jing[1];Shi, Xiao-Xin[1];Yan, Jing-Jing[1];Xing, Jing[1];Zhang, Qiang[1];Xiao, Sen[1]

机构：[1]E China Univ Sci & Technol, Dept Pharmaceut Engn, Sch Pharm, Shanghai 200237, Peoples R China

年份：2010

卷号：2010

期号：36

起止页码：6987

外文期刊名：EUROPEAN JOURNAL OF ORGANIC CHEMISTRY

收录：;WOS:【SCI-EXPANDED(收录号:WOS:000285311000015)，CCR-EXPANDED(收录号:WOS:000285311000015)】；

基金：We thank the National Natural Science Foundation of China (grant number 20972048) and Shanghai Educational Development Foundation (Dawn Program, grant number 03SG27) for the financial support of this work.

语种：英文

外文关键词：Synthetic methods; Heterocycles; Nitrogen heterocycles; Dehydrogenation

摘要：An efficient, practical, and general method for conversions of N-tosyltetrahydroisoquinolines (N-tosyl-THIQs) into isoquinolines and of N-tosyltetrahydro-beta-carbolines (N-tosyl-THBCs) into beta-carbolines is described. Treatment of N-tosyl-THIQs or N-tosyl-THBCs with base in dimethyl sulfoxide afforded dihydroisoquinolines or dihydro-beta-carbolines as intermediates, and these were then oxidized in situ by molecular oxygen to furnish isoquinolines or beta-carbolines in good to high yields. Both one-pot conversions occurred through tandem beta-elimination and aromatization.