A Photoinduced Cascade for the Synthesis of 1H‐Indole‐2‐Acetamide Derivatives

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 derivative...

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Bibliographic Details
Published in:Asian journal of organic chemistry 2019-07, Vol.8 (7), p.1111-1114
Main Authors: Borger, Maribel, Callen, Daniel P., Frederich, James H.
Format: Article
Language:English
Subjects:
Derivatives
heterocycles
indoles
Isomerization
Organic chemistry
photochemistry
pyridazines
synthetic methods
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Summary: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. Transient photo: A method to convert 2‐aminoaryl‐substituted pyridazine N‐oxides to 1H‐indole‐2‐acetamides under the synergic action of UV light and transition‐metal catalysis is reported. This photoinduced cascade reaction passes through a transient 2‐aminofuran intermediate and facilitates synthetic entry to indole motifs that are unavailable by conventional methods.
ISSN:2193-5807
2193-5815
DOI:10.1002/ajoc.201900201