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Tailor‐Made Synthesis of N , N ,2,6‐Tetrasubstituted 4‐Nitroanilines by Three‐Component Ring Transformation of Dinitropyridone
Author(s) -
Le Song Thi,
Asahara Haruyasu,
Nishiwaki Nagatoshi
Publication year - 2015
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201403652
Subject(s) - chemistry , ring (chemistry) , ammonium acetate , ketone , benzene , transformation (genetics) , component (thermodynamics) , nitrogen , medicinal chemistry , ammonium , organic chemistry , stereochemistry , combinatorial chemistry , high performance liquid chromatography , biochemistry , physics , gene , thermodynamics
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.