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Abnormal reactions of 2‐methoxy‐4,9‐dimethyl‐1‐nitroacridine with selenous acid and selenium(IV) oxide. Synthesis of 1 H ‐selenopheno[2,3,4‐ k , l ]acridine‐1‐one: A new seleno‐containing ring system
Author(s) -
Radchenko Oleg S.,
Sigida Ele.,
Balaneva Nadezhda N.,
Dmitrenok Pavel S.,
Novikov Vyacheslav L.
Publication year - 2011
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.512
Subject(s) - chemistry , yield (engineering) , selenium , acridine , ethanol , medicinal chemistry , oxide , ring (chemistry) , organic chemistry , metallurgy , materials science
Unusual course of the reaction was revealed on the oxidation of functionally substituted acridine containing the activated methyl groups by well‐known oxidants, such as selenous acid and selenium(IV) oxide. Treatment of 2‐methoxy‐4,9‐dimethyl‐1‐nitroacridine ( 5 ) with an excess of H 2 SeO 3 in boiling ethanol gave a mixture of the normal reaction products, 2‐methoxy‐4‐methyl‐1‐nitro‐9‐formylacridine ( 11 ) (isolated yield 29%) and 2‐methoxy‐4‐methyl‐1‐nitroacridine‐9‐carboxylic acid ( 12 ) (36%), together with an abnormal product, 3‐methoxy‐5‐methyl‐1 H ‐selenopheno[2,3,4‐ k,l ]acridine‐1‐one ( 13 ) (21%), which is the first example of a new seleno‐containing ring system. With the use of SeO 2 the yield of selenolactone 13 was much lower. J. Heterocyclic Chem., 2011.