Open AccessPyridazine N-Oxides as Precursors to 2-Aminofurans: Scope and Limitations in Complexity Building Cascade Reactions
Author(s) -
Maribel Borger,
James H. Frederich
Publication year - 2019
Publication title -
organic letters
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.94
H-Index - 239
eISSN - 1523-7060
pISSN - 1523-7052
DOI - 10.1021/acs.orglett.9b00682
Subject(s) - chemistry , synthon , pyridazine , combinatorial chemistry , catalysis , reactivity (psychology) , cascade , benzothiazole , scope (computer science) , organic chemistry , computer science , medicine , alternative medicine , pathology , chromatography , programming language
A method to transform pyridazine N-oxides into 2-aminofurans using a combination of UV light and transition metal catalysis has been developed. These electron-rich species exhibit a surprising range of useful reactivity, including the ability to participate in complexity building cascade processes when reacted with dienophiles. This study also establishes 2-aminofurans as valuable synthons that support modular synthetic entry to the shared heterocyclic core of certain aspidosperma and amaryllidaceae alkaloids.