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On the synthesis and animation of 5‐chloro‐and 5‐bromo‐1,7‐naphthyridine
Author(s) -
Woźaniak M.,
van der Plas H. C.
Publication year - 1978
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.5570150505
Subject(s) - chemistry , liquid ammonia , amination , amide , yield (engineering) , potassium , medicinal chemistry , ammonia , organic chemistry , combinatorial chemistry , catalysis , materials science , metallurgy
A new synthesis of 5‐chloro‐ and 5‐bromo‐1,7‐naphthyridine, using 8‐amino‐1,7‐naphthyridine as starting material is described. On amination with potassium amide in liquid ammonia, the 5‐bromo compound undergoes a tele‐amination into 8‐amino‐ and 2‐amino‐1,7‐naphthyridine and a Chichibabin reaction yielding 8‐amino‐5‐bromo‐1,7‐naphthyridine. The reaction with the 5‐chloro compound occurs at a much lower rate than the 5‐bromo compound and only gives 8‐amino‐5‐chloro‐1,7‐naphthyridine in a small yield. Convincing 1 H‐nmr evidence is presented, showing that the 5‐bromo‐ and 5‐chloro‐1,7‐naphthyridine give addition of the amide ion at position 8 and that the 5‐chloro compound also gives addition at position 2.