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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
a   State 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
b   Beijing 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
a   State 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
b   Beijing 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  ∗
a   State 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
b   Beijing 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
c   State Key Laboratory of Functions and Applications of Medicinal Plants, Guizhou Medical University, Guiyang 550014, P. R. of China
,
Heng Xu  ∗
a   State 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
b   Beijing 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
› Author AffiliationsWe gratefully acknowledge the National Natural Science Foundation of China (22077141), the Chinese Academy of Medical Sciences (CAMS) Innovation Fund for Medical Sciences (CIFMS) (2021-I2M-1-026 and 2022-I2M-JB-011), Beijing Outstanding Young Scientist Program (BJJWZYJH01201910023028), Guizhou Medical University (FAMP202003K), and Guizhou Science and Technology Platform Talents (QKHRCPT [2019]5106).
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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

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0041-1738453.
  • Supporting Information


Publication History

Received: 30 June 2023

Accepted after revision: 16 August 2023

Article published online:
21 September 2023

© 2023. Thieme. All rights reserved

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