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One-pot synthesis of 4-methyl-2-alkyl quinazoline-N-oxides by cascade acetamidation–acylation of simple electron-rich arenes with primary nitroalkanes

One-pot synthesis of 4-methyl-2-alkyl quinazoline-N-oxides by cascade acetamidation–acylation of simple electron-rich arenes with primary nitroalkanes

A one-pot, two-stage reaction sequence leading to 2,4-dialkylquinazoline-3-oxide derivatives has been developed. It begins with the in situ formation of anilides by the Beckmann-type acetamidation of simple, bearing electron-donating groups arenes with primary nitroalkanes in polyphosphoric acid. Su...

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Autori principali: Grishin, I. Y., Гришин, И. Ю., Aksenov, D. A., Аксенов, Д. А., Aksenov, N. A., Аксенов, Н. А., Grishin, Y. I., Гришин, Ю. И., Leontiev, A. V., Леонтьев, А. В., Aksenov, A. V., Аксенов, А. В.
Natura: Статья
Lingua:English
Pubblicazione: Elsevier Ltd 2025
Soggetti:
Acylamidation
Quinazolines
Aliphatic nitroalkanes
Beckmann rearrangement
Cascade transformations
Polyphosphoric acid
Heterocyclic compounds
Accesso online:https://dspace.ncfu.ru/handle/123456789/30390
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Riassunto:A one-pot, two-stage reaction sequence leading to 2,4-dialkylquinazoline-3-oxide derivatives has been developed. It begins with the in situ formation of anilides by the Beckmann-type acetamidation of simple, bearing electron-donating groups arenes with primary nitroalkanes in polyphosphoric acid. Subsequent acylation with nitroethane results in the corresponding oximes that react with the neighboring, previously introduced o-anilide moiety to afford the target cyclic N-oxide. Thus, the precursors for this procedure are easily accessible electron-rich arenes unlike the cycloaddition pathways described in the literature that rely almost entirely on o-aminoarylketones whose synthetic and commercial availability is somewhat limited.

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