- 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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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 2SeO3 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.
- Radchenko, Oleg S.,Sigida, Elena N.,Balaneva, Nadezhda N.,Dmitrenok, Pavel S.,Novikov, Vyacheslav L.
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experimental part
p. 209 - 214
(2011/04/15)
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