Pyridazine N-Oxides as Precursors to 2-Aminofurans: Scope and Limitations in Complexity Building Cascade Reactions | Zendy

Maribel Borger | Zendy; James H. Frederich | Zendy

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Pyridazine 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 , pyridazine , synthon , combinatorial chemistry , reactivity (psychology) , catalysis , cascade , scope (computer science) , benzothiazole , 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.

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