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The preparation of 3‐aminoanthyridine
Author(s) -
Carboni S.,
Da Settimo A.,
Bertini D.,
Ferrarini P. L.,
Livi O.,
Tonetti I.
Publication year - 1972
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.5570090406
Subject(s) - chemistry , nitration , raney nickel , aromatization , nitrobenzene , yield (engineering) , organic chemistry , boiling , flue gas desulfurization , hydrogen , catalysis , materials science , metallurgy
Nitration of anthyridine‐2,6‐dione (I) gave 7‐nitroanthyridine‐2,6‐dione (II). Treatment of this compound with phosphorus pentasulfide afforded 7‐aminoanthyridine‐2,6‐dithione (III). Desulfurization of the thioderivative III with Raney Nickel and subsequent aromatization of 3‐amino‐5,10‐dihydroanthyridine (VI) in boiling nitrobenzene, gave 3‐aminoanthyridine (VII) in satisfactory yield. The structure of 3‐aminoanthyridine was demonstrated and its physico‐chemical features are not in agreement with that previously reported in literature. The preparation of 3‐aminoanthyridine‐5‐one (XII) is also described.