Chinese Journal of Organic Chemistry >
Iron(Ⅲ) Porphyrin Catalyzed Cyclization of Ketones with Dimethyl Sulfoxide and Ammonium Acetate: One-Pot Synthesis of Pyridines
Received date: 2018-09-07
Revised date: 2018-11-29
Online published: 2018-12-05
Supported by
Project supported by the National Natural Science Foundations of China (No. 21572049).
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.
Key words： pyridine; iron (III) porphyrin; dimethyl sulfoxide; ketone
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
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