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 |
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| Authors: | Oleg S. Radchenko Elena N. Sigida Nadezhda N. Balaneva Pavel S. Dmitrenok Vyacheslav L. Novikov |
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| Affiliation: | 1. Pacific Institute of Bioorganic Chemistry, Far‐Eastern Branch of the Russian Academy of Sciences, 159 Prosp. 100 let Vladivostoku, 690022, Vladivostok‐22, Russian Federation;2. Department of Chemistry, Far Eastern National University, 8 Sukhanova Str., 690050, Vladivostok‐50, Russian Federation |
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| 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 H2SeO3 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‐1H‐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 SeO2 the yield of selenolactone 13 was much lower. J. Heterocyclic Chem., 2011. |
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