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Amination of 3,6‐dinitro‐1,8‐naphthyridines
Author(s) -
Wozniak M.,
Plas C. Van Der
Publication year - 1986
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570230232
Subject(s) - amination , chemistry , adduct , covalent bond , potassium permanganate , alkoxy group , potassium , liquid ammonia , reductive amination , medicinal chemistry , amino acid , ammonia , organic chemistry , biochemistry , catalysis , alkyl
Treatment of 2‐amino‐3,6‐dinitro‐1,8‐naphthyridines with liquid ammonia/potassium permanganate gives 2,4‐diamino‐3,6‐dinitro‐1,8‐naphthyridine. From 2‐ethoxy‐3,6‐dinitro‐1,8‐naphthyridine a mixture of 4‐amino‐and 5‐amino‐3,6‐dinitro‐1,8‐naphthyridine was obtained. 2‐Chloro‐3,6‐dinitro‐1,8‐naphthyridine afforded a mixture of four compounds i. e. 2,4‐ and 2,5‐diamino‐3,6‐dinitro‐1,8‐naphthyridine and 2‐chloro‐5‐amino‐3,6‐dinitro‐1,8‐naphthyridine and 2‐amino‐3,6‐dinitro‐1,8‐naphthyridine. A study on covalent amination has shown that 4‐amino‐2‐ethoxy‐3,6‐dinitro‐1,8‐naphthyridine undergoes covalent amination at C‐5, whereupon in this adduct amino‐deethoxylation takes place. In a similar way, 2‐chloro‐ and 2‐ethoxy‐5‐amino‐3,6‐dinitro‐1,8‐naphthyridine give covalent amination at C‐4.