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

• Published in: Journal of heterocyclic chemistry Vol. 48; no. 1; pp. 209 - 214
• Main Authors: Radchenko, Oleg S., Sigida, Elena N., Balaneva, Nadezhda N., Dmitrenok, Pavel S., Novikov, Vyacheslav L.
• Format: Journal Article
• Language: English
• Published: 01-01-2011
• ISSN: 0022-152X; 1943-5193
• DOI: 10.1002/jhet.512

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.