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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| Príomhchruthaitheoirí: | , , , , , , , , , , , |
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| Formáid: | Статья |
| Teanga: | English |
| Foilsithe / Cruthaithe: |
Elsevier Ltd
2025
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| Ábhair: | |
| Rochtain ar líne: | https://dspace.ncfu.ru/handle/123456789/30390 |
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| Achoimre: | 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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