A versatile switching method for N- or O-alkylation of 2-aminophenols using ionic liquids: Selective access to benzo[1,4]oxazine-2-one and benzo[1,4]oxazine-3-one derivatives

被引：1

作者：

Shabpiray, Mohammad ^{[1
]}

Sharifi, Ali ^{[1
]}

Abaee, M. Saeed ^{[1
]}

Mirzaei, Moitaba ^{[1
]}

Ghonouei, Nima ^{[1
]}

机构：

[1] Chem & Chem Engn Res Ctr Iran, Fac Organ Chem & Nat Prod, Pajohesh Blvrd, Tehran 1496813151, Iran

来源：

TETRAHEDRON LETTERS | 2023年 / 126卷

关键词：

Benzoxazineones; Ionic liquids; Chemoselective synthesis; Switching method; Heterocyclic chemistry; AMINOPHENOLS; METAL; ACIDS; AGENTS; BASE;

D O I：

10.1016/j.tetlet.2023.154643

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A new method is developed for efficient and chemoselective synthesis of benzo[1,4]oxazineone deriva-tives. By the choice of an appropriate ionic liquid, the process is directed towards selective O- or N-alky-lation to give the desired isomeric structures, as the major product of the reaction. In the presence of choline hydroxide, benzo[1,4]oxazine-3-one derivatives are formed, while by using choline fluoride, the corresponding benzo[1,4]oxazine-2-ones are obtained. The latter pathway would be facilitated for sluggish reactants by in situ use of an alkyl halide. & COPY; 2023 Elsevier Ltd. All rights reserved.

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页数：5

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