Heterocycle-guided synthesis of <i>m</i>-hetarylanilines via three-component benzannulation

A one-pot three-component synthesis of substituted <i>meta</i>-hetarylanilines from heterocycle-substituted 1,3-diketones has been developed. The electron-withdrawing power of the heterocyclic substituent (which can be estimated on the basis of calculated Hammett constants) in the 1,3-diketone plays a pivotal role in the studied reaction. The series of <i>meta</i>-hetarylanilines prepared (21-85% isolated yield) demonstrates the synthetic utility of the developed method.

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Publication Details

Journal
Beilstein Journal of Organic Chemistry
Published
2024-09-02
DOI
https://doi.org/10.3762/bjoc.20.188
Primary Topic
Catalytic C–H Functionalization Methods
Type
article
Field-Weighted Citation Impact
0.00

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article

Heterocycle-guided synthesis of m-hetarylanilines via three-component benzannulation

Andrew R. Galeev, А. Н. Масливец, Alexander S. Novikov, М. В. Дмитриев
1 links
Beilstein Journal of Organic Chemistry
Catalytic C–H Functionalization Methods
article

Heterocycle-guided synthesis of m-hetarylanilines via three-component benzannulation

Andrew R. Galeev, А. Н. Масливец, Alexander S. Novikov, М. В. Дмитриев
article en

Abstract

A one-pot three-component synthesis of substituted <i>meta</i>-hetarylanilines from heterocycle-substituted 1,3-diketones has been developed. The electron-withdrawing power of the heterocyclic substituent (which can be estimated on the basis of calculated Hammett constants) in the 1,3-diketone plays a pivotal role in the studied reaction. The series of <i>meta</i>-hetarylanilines prepared (21-85% isolated yield) demonstrates the synthetic utility of the developed method.

Beilstein Journal of Organic ChemistryVol. 20
Perm State University (RU), Peoples' Friendship University of Russia (RU), St Petersburg University (RU)
Ministry of Science and Higher Education of the Russian Federation, RUDN University
Openalex Percentile: Top 90%
Catalytic C–H Functionalization Methods
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Heterocycle-guided synthesis of <i>m</i>-hetarylanilines via three-component benzannulation — Andrew R. Galeev, А. Н. Масливец, et al. · Beilstein Journal of Organic Chemistry (2024) | TGRS Research Map | TGRS