Abnormal reactions of 2-methoxy-4,9-dimethyl-1-nitroacridine with selenous acid and selenium(IV) oxide. Synthesis of 1H-selenopheno[2,3,4-k,l]acridine-1-one: A new seleno-containing ring system

✍ Scribed by Oleg S. Radchenko; Elena N. Sigida; Nadezhda N. Balaneva; Pavel S. Dmitrenok; Vyacheslav L. Novikov

• Publisher: Journal of Heterocyclic Chemistry
• Year: 2010
• Tongue: English
• Weight: 150 KB
• Volume: 48
• Category: Article
• ISSN: 0022-152X
• DOI: 10.1002/jhet.512

✦ Synopsis

Abstract

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.