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.
Readily prepared 3-(2-aminoaryl)-6-aminopyridazine N-oxides undergo a photoinduced cascade transformation to furnish 1H-indole-2-acetamides. The reported method uniquely proceeds via acid-catalyzed isomerization of a 2-aminofuran intermediate and supports modular synthetic entry to indole derivatives that would be difficult to access by any other means.[a] M.
scite is a Brooklyn-based organization that helps researchers better discover and understand research articles through Smart Citations–citations that display the context of the citation and describe whether the article provides supporting or contrasting evidence. scite is used by students and researchers from around the world and is funded in part by the National Science Foundation and the National Institute on Drug Abuse of the National Institutes of Health.