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

A highly regioselective method was developed for the preparation of pyridazine derivatives via the aza-Diels–Alder reaction of 1,2,3-triazines with 1-propynylamines under neutral conditions. This methodology allowed direct access to a wide range of 6-aryl-pyridazin-3-amines in high yields with good...

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Published inJournal of organic chemistry Vol. 86; no. 13; pp. 8926 - 8932
Main Authors Kodama, Takayuki, Sasaki, Ikuo, Sugimura, Hideyuki
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 02.07.2021
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
CYCLOADDITION
ROUTE
AZAMERONE
ACID
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Summary:A highly regioselective method was developed for the preparation of pyridazine derivatives via the aza-Diels–Alder reaction of 1,2,3-triazines with 1-propynylamines under neutral conditions. This methodology allowed direct access to a wide range of 6-aryl-pyridazin-3-amines in high yields with good functional group compatibility. Key features of this strategy included a broad substrate scope and simple, metal-free, and neutral reaction conditions.
Bibliography:ObjectType-Article-1
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ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.1c00851