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Synthesis of New Substituted 4‐Amino‐3,5‐dinitropyridine Derivatives
Author(s) -
Ma Congming,
Wang Yongbin,
Hou Kehui,
Liu Zuliang,
Yao Qizheng
Publication year - 2013
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201300534
Subject(s) - chemistry , methylamine , nucleophilic substitution , sodium azide , nitration , azide , pyridine , medicinal chemistry , potassium fluoride , ring (chemistry) , amine gas treating , derivative (finance) , substitution reaction , organic chemistry , fluoride , inorganic chemistry , financial economics , economics
Facile synthetic routes for the preparation of some new 4‐amino‐3,5‐dinitropyridine derivatives have been revealed. Nitration of 2‐chloropyridin‐4‐amine ( 1 ) as a starting material, in an unexpected one‐step reaction, to give dinitrated derivatives, followed by nucleophilic substitution reactions with sodium azide, potassium fluoride, ammonia, methylamine, and 4‐nitroimidazol, respectively, gave substituted 4‐amino‐3,5‐dinitropyridine derivatives. Meanwhile, its azide derivative underwent a ring closure conversion into 7‐amino‐6‐nitro‐[1,2,5]oxadiazolo[3,4‐ b ]pyridine‐1‐oxide. It is of significance that all of the nucleophilic substitution reactions were carried out under mild conditions.