Issue 47, 2019

A novel methodology for the synthesis of condensed selenium heterocycles based on the annulation and annulation–methoxylation reactions of selenium dihalides

Abstract

A novel methodology to accelerate annulation reactions leading to condensed selenium heterocycles was developed. The reactions of selenium dihalides with methyleugenol, allyl thymyl ether, allyl 1-naphthyl and 1-naphthyl propargyl ethers were carried out in the presence of alcohols, which considerably accelerated the annulation reactions. In solvent systems CH2Cl2/MeOH or CHCl3/MeOH, the reactions proceeded as annulation–methoxylation affording condensed methoxylated heterocycles. In the presence of isopropanol, the reactions were not accompanied by alkoxylation giving condensed halogen-containing products. The annulation reaction of selenium dihalides with 1-naphthyl propargyl ether included stereoselective anti-addition to the triple bond. The efficient selective synthesis of the first representatives of novel families of condensed selenium heterocycles with promising biological activity was developed.

Graphical abstract: A novel methodology for the synthesis of condensed selenium heterocycles based on the annulation and annulation–methoxylation reactions of selenium dihalides

Supplementary files

Article information

Article type
Paper
Submitted
13 9月 2019
Accepted
05 11月 2019
First published
05 11月 2019

New J. Chem., 2019,43, 18476-18483

A novel methodology for the synthesis of condensed selenium heterocycles based on the annulation and annulation–methoxylation reactions of selenium dihalides

M. V. Musalov, V. A. Yakimov, V. A. Potapov, S. V. Amosova, T. N. Borodina and S. V. Zinchenko, New J. Chem., 2019, 43, 18476 DOI: 10.1039/C9NJ04707G

To request permission to reproduce material from this article, please go to the Copyright Clearance Center request page.

If you are an author contributing to an RSC publication, you do not need to request permission provided correct acknowledgement is given.

If you are the author of this article, you do not need to request permission to reproduce figures and diagrams provided correct acknowledgement is given. If you want to reproduce the whole article in a third-party publication (excluding your thesis/dissertation for which permission is not required) please go to the Copyright Clearance Center request page.

Read more about how to correctly acknowledge RSC content.

Social activity

Spotlight

Advertisements