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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.
- Source :
-
New Journal of Chemistry . 12/21/2019, Vol. 43 Issue 47, p18476-18483. 8p. - Publication Year :
- 2019
-
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. [ABSTRACT FROM AUTHOR]
- Subjects :
- *SELENIUM
*ANNULATION
*HETEROCYCLIC compounds
*ALKOXYLATION
*ETHERS
Subjects
Details
- Language :
- English
- ISSN :
- 11440546
- Volume :
- 43
- Issue :
- 47
- Database :
- Academic Search Index
- Journal :
- New Journal of Chemistry
- Publication Type :
- Academic Journal
- Accession number :
- 140030950
- Full Text :
- https://doi.org/10.1039/c9nj04707g