Synthesis of (Het)aryl 2-(2-Hydroxyaryl)cyclopropyl Ketones

Synthesis of (Het)aryl 2-(2-Hydroxyaryl)cyclopropyl Ketones

A simple general method for the synthesis of 1-acyl-2-(<i>ortho</i>-hydroxyaryl)cyclopropanes, which belong to the donor–acceptor cyclopropane family, has been developed. This method, based on the Corey–Chaykovsky cyclopropanation of 2-hydroxychalcones, allows for the preparation of a la...

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Main Authors: Alexander A. Fadeev, Alexey O. Chagarovskiy, Anton S. Makarov, Irina I. Levina, Olga A. Ivanova, Maxim G. Uchuskin, Igor V. Trushkov
Format: Article
Language:English
Published: MDPI AG 2020-12-01
Series:Molecules
Subjects:
2-hydroxychalcones
Corey–Chaykovsky cyclopropanation
donor–acceptor cyclopropanes
Online Access:https://www.mdpi.com/1420-3049/25/23/5748
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spelling doaj-fa7e95aef6c748059dfd911ce5ebb5e72020-12-06T00:02:40ZengMDPI AGMolecules1420-30492020-12-01255748574810.3390/molecules25235748Synthesis of (Het)aryl 2-(2-Hydroxyaryl)cyclopropyl KetonesAlexander A. Fadeev0Alexey O. Chagarovskiy1Anton S. Makarov2Irina I. Levina3Olga A. Ivanova4Maxim G. Uchuskin5Igor V. Trushkov6Department of Organic Chemistry, Faculty of Science, Charles University, Hlavova 8, 12800 Prague 2, Czech RepublicN. D. Zelinsky Institute of Organic Chemistry, Leninsky pr. 47, Moscow 119991, RussiaDepartment of Chemistry, Perm State University, Bukireva 15, Perm 614990, RussiaN. M. Emanuel Institute of Biochemical Physcis Russian Academy of Sciences, Kosygina 4, Moscow 117198, RussiaN. D. Zelinsky Institute of Organic Chemistry, Leninsky pr. 47, Moscow 119991, RussiaDepartment of Chemistry, Perm State University, Bukireva 15, Perm 614990, RussiaN. D. Zelinsky Institute of Organic Chemistry, Leninsky pr. 47, Moscow 119991, RussiaA simple general method for the synthesis of 1-acyl-2-(<i>ortho</i>-hydroxyaryl)cyclopropanes, which belong to the donor–acceptor cyclopropane family, has been developed. This method, based on the Corey–Chaykovsky cyclopropanation of 2-hydroxychalcones, allows for the preparation of a large diversity of hydroxy-substituted cyclopropanes, which can serve as promising building blocks for the synthesis of various bioactive compounds.https://www.mdpi.com/1420-3049/25/23/57482-hydroxychalconesCorey–Chaykovsky cyclopropanationdonor–acceptor cyclopropanes
collection DOAJ
language English
format Article
sources DOAJ
author Alexander A. Fadeev
Alexey O. Chagarovskiy
Anton S. Makarov
Irina I. Levina
Olga A. Ivanova
Maxim G. Uchuskin
Igor V. Trushkov
spellingShingle Alexander A. Fadeev
Alexey O. Chagarovskiy
Anton S. Makarov
Irina I. Levina
Olga A. Ivanova
Maxim G. Uchuskin
Igor V. Trushkov
Synthesis of (Het)aryl 2-(2-Hydroxyaryl)cyclopropyl Ketones
Molecules
2-hydroxychalcones
Corey–Chaykovsky cyclopropanation
donor–acceptor cyclopropanes
author_facet Alexander A. Fadeev
Alexey O. Chagarovskiy
Anton S. Makarov
Irina I. Levina
Olga A. Ivanova
Maxim G. Uchuskin
Igor V. Trushkov
author_sort Alexander A. Fadeev
title Synthesis of (Het)aryl 2-(2-Hydroxyaryl)cyclopropyl Ketones
title_short Synthesis of (Het)aryl 2-(2-Hydroxyaryl)cyclopropyl Ketones
title_full Synthesis of (Het)aryl 2-(2-Hydroxyaryl)cyclopropyl Ketones
title_fullStr Synthesis of (Het)aryl 2-(2-Hydroxyaryl)cyclopropyl Ketones
title_full_unstemmed Synthesis of (Het)aryl 2-(2-Hydroxyaryl)cyclopropyl Ketones
title_sort synthesis of (het)aryl 2-(2-hydroxyaryl)cyclopropyl ketones
publisher MDPI AG
series Molecules
issn 1420-3049
publishDate 2020-12-01
description A simple general method for the synthesis of 1-acyl-2-(<i>ortho</i>-hydroxyaryl)cyclopropanes, which belong to the donor–acceptor cyclopropane family, has been developed. This method, based on the Corey–Chaykovsky cyclopropanation of 2-hydroxychalcones, allows for the preparation of a large diversity of hydroxy-substituted cyclopropanes, which can serve as promising building blocks for the synthesis of various bioactive compounds.
topic 2-hydroxychalcones
Corey–Chaykovsky cyclopropanation
donor–acceptor cyclopropanes
url https://www.mdpi.com/1420-3049/25/23/5748
work_keys_str_mv AT alexanderafadeev synthesisofhetaryl22hydroxyarylcyclopropylketones
AT alexeyochagarovskiy synthesisofhetaryl22hydroxyarylcyclopropylketones
AT antonsmakarov synthesisofhetaryl22hydroxyarylcyclopropylketones
AT irinailevina synthesisofhetaryl22hydroxyarylcyclopropylketones
AT olgaaivanova synthesisofhetaryl22hydroxyarylcyclopropylketones
AT maximguchuskin synthesisofhetaryl22hydroxyarylcyclopropylketones
AT igorvtrushkov synthesisofhetaryl22hydroxyarylcyclopropylketones
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