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

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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

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Publication details

The article was received on 13 Sep 2019, accepted on 05 Nov 2019 and first published on 05 Nov 2019


Article type: Paper
DOI: 10.1039/C9NJ04707G
New J. Chem., 2019, Advance Article

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    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, Advance Article , DOI: 10.1039/C9NJ04707G

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