Rhodium-Catalyzed Regioselective Synthesis of N-Secondary Alkyl Indoles via Intermolecular Cyclization of N-Nitrosoanilines and Unsymmetrical Alkynes

Yiting Chang; Tingting Hou; Yi Dong; Heng Xu

doi:10.1055/s-0041-1738453

Synthesis, Inhaltsverzeichnis

Synthesis 2023; 55(23): 3969-3980
DOI: 10.1055/s-0041-1738453

paper

Rhodium-Catalyzed Regioselective Synthesis of N-Secondary Alkyl Indoles via Intermolecular Cyclization of N-Nitrosoanilines and Unsymmetrical Alkynes

Yiting Chang

^aState Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, P. R. of China

^bBeijing Key Laboratory of Active Substances Discovery and Druggability Evaluation, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, P. R. of China

,

Tingting Hou

^aState Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, P. R. of China

^bBeijing Key Laboratory of Active Substances Discovery and Druggability Evaluation, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, P. R. of China

,

Yi Dong ∗

^aState Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, P. R. of China

^bBeijing Key Laboratory of Active Substances Discovery and Druggability Evaluation, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, P. R. of China

^cState Key Laboratory of Functions and Applications of Medicinal Plants, Guizhou Medical University, Guiyang 550014, P. R. of China

,

Heng Xu ∗

^aState Key Laboratory of Bioactive Substance and Function of Natural Medicines, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, P. R. of China

^bBeijing Key Laboratory of Active Substances Discovery and Druggability Evaluation, Institute of Materia Medica, Chinese Academy of Medical Sciences and Peking Union Medical College, Beijing 100050, P. R. of China

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Abstract

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Abstract

A Cp*Rh-catalyzed C–H functionalization/cyclization to afford 2,3-substituted N-secondary alkyl indole derivatives is described. This intermolecular cyclization of N-secondary nitrosoanilines and unsymmetrically substituted alkynes has good performances in yields, substrate scope, and regioselectivities.

Key words

regioselective synthesis - N-secondary alkyl indoles - intermolecular cyclization - N-nitrosoanilines - unsymmetrical alkynes

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Referenzen

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