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Cerium(III)-catalyzed cascade cyclization: an efficient approach to functionalized pyrrolo[1,2-a]quinolines. 2014
Hefei National Laboratory for Physical Science at Microscale, CAS Key Laboratory of Soft Matter Chemistry & Collaborative Innovation Center of Suzhou Nano Science and Technology, University of Science and Technology of China, Hefei, Anhui 230026, P. R. China. zwang3@ustc.edu.cn.
A general and practical route to the synthesis of multisubstituted pyrrolo[1,2-a]quinolines has been described from 2-alkylazaarenes and nitroolefins using cerium chloride as a catalyst via a tandem Michael addition, cyclization and aromatization. This protocol features readily available starting materials, operational simplicity and high regioselectivity to access multifunctionalized pyrrolo[1,2-a]quinolines with the formation of multiple C-C and C-N bonds in one pot. In addition, various substitution patterns and functional groups were found to be compatible under the optimized conditions, which was lacking in the existing procedures.
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