Construction of Imidazole-Fused-Ring Systems by Iron-Catalyzed C(sp3)-H Amination-Cyclization under Aerobic Conditions

Jiangling Peng; Shijia Li; Junwei Huang; Qianli Meng; Lixin Wang; Wenlong Xin; Weini Li; Wei Zhou; Lanyue Zhang

doi:10.1021/acs.joc.3c02078

Construction of Imidazole-Fused-Ring Systems by Iron-Catalyzed C(sp³)-H Amination-Cyclization under Aerobic Conditions

J Org Chem. 2023 Dec 1;88(23):16581-16588. doi: 10.1021/acs.joc.3c02078. Epub 2023 Nov 17.

Authors

Jiangling Peng¹, Shijia Li¹, Junwei Huang¹, Qianli Meng¹, Lixin Wang¹, Wenlong Xin¹, Weini Li², Wei Zhou¹, Lanyue Zhang¹

Affiliations

¹ School of Biomedical and Pharmaceutical Sciences, Guangdong University of Technology, Guangzhou, Guangdong 510006, China.
² Department of Diabetes Complications and Metabolism, Arthur Riggs Diabetes and Metabolism Research Institute, Beckman Research Institute of City of Hope, Duarte, California91010, United States.

PMID: 37976463
DOI: 10.1021/acs.joc.3c02078

Abstract

An iron-catalyzed efficient C-H amination for the construction of imidazole-fused-ring systems was developed under aerobic conditions. Compared to previous studies, this work exhibited green features. The reaction was conducted in the green solvent anisole, with water as the only byproduct. Four C(sp³)-H bonds were cleaved and three C-N bonds were formed in this transformation. Imidazo[1,5-a]pyridine-, imidazo[5,1-b]oxazole-, imidazo[5,1-b]thiazole-, imidazo[1,5-a]pyrazine-, and imidazo[1,5-a]imidazole-related N-heterocycles were obtained in acceptable-to-excellent yield.