Tailor-Made Synthesis of N,N,2,6-Tetrasubstituted 4-Nitroanilines by Three-Component Ring Transformation of Dinitropyridone

The ring transformation of dinitropyridone afforded various kinds of 2,6‐disubstituted‐4‐nitroanilines upon treatment with aliphatic ketones in the presence of ammonium acetate as a nitrogen source, wherein dinitropyridone behaved as the synthetic equivalent of unstable nitromalonaldehyde. The benze...

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Bibliographic Details
Published in:European journal of organic chemistry 2015-02, Vol.2015 (6), p.1203-1206
Main Authors: Le, Song Thi, Asahara, Haruyasu, Nishiwaki, Nagatoshi
Format: Article
Language:English
Subjects:
Ketones
Multicomponent reactions
Nitroheterocycles
Ring transformation
Synthetic methods
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Summary:The ring transformation of dinitropyridone afforded various kinds of 2,6‐disubstituted‐4‐nitroanilines upon treatment with aliphatic ketones in the presence of ammonium acetate as a nitrogen source, wherein dinitropyridone behaved as the synthetic equivalent of unstable nitromalonaldehyde. The benzene ring, as well as the amino group of the nitroaniline framework, was easily modified by only changing a ketone and the nitrogen source, which afforded N,N,2,6‐tetrasubstituted 4‐nitroanilines in good to excellent yields. The ring transformation of dinitropyridone afforded various kinds of N,N,2,6‐tetrasubstituted 4‐nitroanilines, of which the benzene ring as well as the amino group was easily modified by only changing a ketone and an amine.
ISSN:1434-193X
1099-0690
DOI:10.1002/ejoc.201403652