Rhodium-Catalyzed [4 + 2] Cascade Annulation to Easy Access N-Substituted Indenoisoquinolinones
Xuelin Yue1, Yijie Gao1, Junwei Huang1
1Engineering Research Centre of Molecular Medicine of Ministry of Education, Key Laboratory of Fujian Molecular Medicine, Key Laboratory of Precision Medicine and Molecular Diagnosis of Fujian Universities, Key Laboratory of Xiamen Marine and Gene Drugs, School of Biomedical Sciences, Huaqiao University, Xiamen 361021, P. R. China.
Abstract:
An efficient approach for the synthesis of N-substituted indenoisoquinolinones via rhodium(III)-catalyzed C-H bond activation/subsequent [4 + 2] cyclization starting from easily available 2-phenyloxazolines and 2-diazo-1,3-indandiones has been developed. A series of indeno[1,2-c]isoquinolinones were obtained in up to 93% yield through C-H functionalization, followed by intramolecular annulation, elimination, and ring-opening in a "one pot manner" under mild reaction conditions. This protocol features excellent atom- and step-economy and provides a novel strategy for the synthesis of N-substituted indenoisoquinolinones and a chance to study their biological activities.
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