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

Alexander A Fadeev; Alexey O Chagarovskiy; Anton S Makarov; Irina I Levina; Olga A Ivanova; Maxim G Uchuskin; Igor V Trushkov

doi:10.3390/molecules25235748

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

Molecules. 2020 Dec 5;25(23):5748. doi: 10.3390/molecules25235748.

Authors

Alexander A Fadeev^{1

2}, Alexey O Chagarovskiy^{3

4}, Anton S Makarov², Irina I Levina⁵, Olga A Ivanova^{3

6}, Maxim G Uchuskin², Igor V Trushkov^{3

4}

Affiliations

¹ Department of Organic Chemistry, Faculty of Science, Charles University, Hlavova 8, 12800 Prague 2, Czech Republic.
² Department of Chemistry, Perm State University, Bukireva 15, Perm 614990, Russia.
³ N. D. Zelinsky Institute of Organic Chemistry, Leninsky pr. 47, Moscow 119991, Russia.
⁴ Dmitry Rogachev National Medical Research Center of Pediatric Hematology, Oncology and Immunology, Samory Mashela 1, Moscow 117997, Russia.
⁵ N. M. Emanuel Institute of Biochemical Physcis Russian Academy of Sciences, Kosygina 4, Moscow 117198, Russia.
⁶ Department of Chemistry, M. V. Lomonosov Moscow State University, Leninskie gory 1-3, Moscow 119991, Russia.

Abstract

A simple general method for the synthesis of 1-acyl-2-(ortho-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.

Keywords: 2-hydroxychalcones; Corey–Chaykovsky cyclopropanation; donor–acceptor cyclopropanes.

MeSH terms

Biological Factors / chemistry
Cyclopropanes / chemistry*
Ketones / chemistry*

Substances

Biological Factors
Cyclopropanes
Ketones
cyclopropane

Grants and funding

18-13-00449/Russian Science Foundation