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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Главные авторы:	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.
Formato:	Статья
Idioma:	English
Publicado:	Elsevier Ltd 2025
Темы:	Acylamidation Quinazolines Aliphatic nitroalkanes Beckmann rearrangement Cascade transformations Polyphosphoric acid Heterocyclic compounds
Acceso en liña:	https://dspace.ncfu.ru/handle/123456789/30390
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spelling	ir-123456789-303902025-04-03T12:01:59Z One-pot synthesis of 4-methyl-2-alkyl quinazoline-N-oxides by cascade acetamidation–acylation of simple electron-rich arenes with primary nitroalkanes 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. Acylamidation Quinazolines Aliphatic nitroalkanes Beckmann rearrangement Cascade transformations Polyphosphoric acid Heterocyclic compounds 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. 2025-04-03T12:00:26Z 2025-04-03T12:00:26Z 2025 Статья Grishin I.Y., Aksenov D.A., Aksenov N.A., Grishin Y.I., Leontiev A.V., Aksenov A.V. One-pot synthesis of 4-methyl-2-alkyl quinazoline-N-oxides by cascade acetamidation–acylation of simple electron-rich arenes with primary nitroalkanes // Tetrahedron. - 2025. - 177. - art. no. 134589. - DOI: 10.1016/j.tet.2025.134589 https://dspace.ncfu.ru/handle/123456789/30390 en Tetrahedron application/pdf application/pdf Elsevier Ltd
institution	СКФУ
collection	Репозиторий
language	English
topic	Acylamidation Quinazolines Aliphatic nitroalkanes Beckmann rearrangement Cascade transformations Polyphosphoric acid Heterocyclic compounds
spellingShingle	Acylamidation Quinazolines Aliphatic nitroalkanes Beckmann rearrangement Cascade transformations Polyphosphoric acid Heterocyclic compounds 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. One-pot synthesis of 4-methyl-2-alkyl quinazoline-N-oxides by cascade acetamidation–acylation of simple electron-rich arenes with primary nitroalkanes
description	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.
format	Статья
author	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.
author_facet	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.
author_sort	Grishin, I. Y.
title	One-pot synthesis of 4-methyl-2-alkyl quinazoline-N-oxides by cascade acetamidation–acylation of simple electron-rich arenes with primary nitroalkanes
title_short	One-pot synthesis of 4-methyl-2-alkyl quinazoline-N-oxides by cascade acetamidation–acylation of simple electron-rich arenes with primary nitroalkanes
title_full	One-pot synthesis of 4-methyl-2-alkyl quinazoline-N-oxides by cascade acetamidation–acylation of simple electron-rich arenes with primary nitroalkanes
title_fullStr	One-pot synthesis of 4-methyl-2-alkyl quinazoline-N-oxides by cascade acetamidation–acylation of simple electron-rich arenes with primary nitroalkanes
title_full_unstemmed	One-pot synthesis of 4-methyl-2-alkyl quinazoline-N-oxides by cascade acetamidation–acylation of simple electron-rich arenes with primary nitroalkanes
title_sort	one-pot synthesis of 4-methyl-2-alkyl quinazoline-n-oxides by cascade acetamidation–acylation of simple electron-rich arenes with primary nitroalkanes
publisher	Elsevier Ltd
publishDate	2025
url	https://dspace.ncfu.ru/handle/123456789/30390
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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

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