Citation: Liu Yufeng, Cao Zhongzhong, Su Miaodong, Li Hui, Fu Meiqiang, Liu Qiang, Luo Weiping, Guo Cancheng. Iron(Ⅲ) Porphyrin Catalyzed Cyclization of Ketones with Dimethyl Sulfoxide and Ammonium Acetate: One-Pot Synthesis of Pyridines[J]. Chinese Journal of Organic Chemistry, ;2019, 39(1): 129-136. doi: 10.6023/cjoc201809014 shu

Iron(Ⅲ) Porphyrin Catalyzed Cyclization of Ketones with Dimethyl Sulfoxide and Ammonium Acetate: One-Pot Synthesis of Pyridines

a.
Advanced Catalytic Engineering Research Center of the Ministry of Education, College of Chemistry and Chemical Engineering, Hunan University, Changsha 410082

Corresponding author: Guo Cancheng, ccguo@hnu.edu.cn
Received Date: 7 September 2018
Revised Date: 29 November 2018
Available Online: 5 January 2018
Fund Project: the National Natural Science Foundations of China 21572049Project supported by the National Natural Science Foundations of China (No. 21572049)

Figures(2)

An iron(Ⅲ)-porphyrin-catalyzed cyclization of ketones with dimethyl sulfoxide (DMSO) and ammonium acetate for the synthesis of unsymmetrical and symmetrical pyridines by employing DMSO as C₄ or C₆ source has been developed. Various aryl ketone derivatives react readily with DMSO, producing the pyridines in yields of 30%~85%. This method uses non-noble metals and proceeds under mild reaction conditions with operational simplicity, which thus allows the expedient assembly of pyridines from readily available ketones. Based on the preliminary experiments, a plausible mechanism of this transformation is disclosed.
- pyridine,
- iron(Ⅲ) porphyrin,
- dimethyl sulfoxide,
- ketone
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