3-Formylpyrroles from 3-Furfurylamines by Bromine Oxidation Reaction

Oxidation of 3‐furfurylamines 3a‐e with bromine in acetone‐water solution gave N‐substituted 3‐formylpyrroles 4a‐e in good yields. A reaction mechanism via the Clauson‐Kaas reaction followed by the cis‐trans isomerization of the 2‐ene‐1,4‐diones 13 and 14 was proposed to account for the formation of...

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Bibliographic Details
Published in:Journal of the Chinese Chemical Society (Taipei) 2010-12, Vol.57 (6), p.1321-1326
Main Authors: Harn, Piin-Jye, Lin, Chu-Chung, Wu, Hsien-Jen
Format: Article
Language:English
Subjects:
3-Formylpyrroles
3-Furfurylamines
Oxidation with bromine
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Summary:Oxidation of 3‐furfurylamines 3a‐e with bromine in acetone‐water solution gave N‐substituted 3‐formylpyrroles 4a‐e in good yields. A reaction mechanism via the Clauson‐Kaas reaction followed by the cis‐trans isomerization of the 2‐ene‐1,4‐diones 13 and 14 was proposed to account for the formation of the pyrroles 4a‐e. Oxidation of 3‐furfurylamines with bromine in acetone‐water solution gave N‐substituted 3‐formylpyrroles in good yields.
ISSN:0009-4536
2192-6549
DOI:10.1002/jccs.201000195