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Diversity-oriented synthesis of imidazo[2,1-a]isoquinolines
Shaoyu Mai1, Yixin Luo, Xianyun Huang
1Institute of Next Generation Matter Transformation, College of Chemical Engineering at Huaqiao University, 668 Jimei Blvd, Xiamen, Fujian 361021, P. R. China. qsong@hqu.edu.cn.
Abstract:
Herein, we report an efficient and practical strategy for the synthesis of five types of imidazo[2,1-a]isoquinolines via Cp*RhIII-catalyzed [4+2] annulation of 2-arylimidazoles and α-diazoketoesters, whose structural and substituted diversity at 5- or 6-position can be precisely controlled by the α-diazoketoester coupling partners. Compared with previous reports, in this study, we merged two attractive C-C cleavage strategies (retro-Claisen and decarboxylation) into the classical C-H functionalization/condensation process by choosing appropriate ester groups (-COOEt, -COOtBu or -COOiPr) or inexpensive additives (HOAc or KOAc). Moreover, the synthetic efficacies of these methods were demonstrated by the concise synthesis of several bioactive compounds and the late-stage modification of representative drugs.
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