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Synthesis of Pyridazine Derivatives via Aza-Diels-Alder Reactions of 1,2,3-Triazine Derivatives and 1-Propynylamines

Takayuki Kodama, Ikuo Sasaki and Hideyuki Sugimura*

*Department of Chemistry and Bioscience, Faculty of Science and Technology, Aoyama Gakuin University, 5-10-1, Fuchinobe, Chuo-ku, Sagamihara 252-5258, Japan, Email: sugimurachem.aoyama.ac.jp

T. Kodama, I. Sasaki, H. Sugimura, J. Org. Chem., 2021, 86, 8926-8932.

DOI: 10.1021/acs.joc.1c00851 (free Supporting Information)



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Abstract

An aza-Diels-Alder reaction of 1,2,3-triazines with 1-propynylamines enables a highly regioselective synthesis of 6-aryl-pyridazin-3-amines in high yields under neutral conditions. This reaction offers good functional group compatibility, broad substrate scope and simple, metal-free, and neutral reaction conditions.

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proposed reaction pathway



Key Words

Pyridazines, Diels-Alder Reaction


ID: J42-Y2021