Synthesis of Chalcogenylchromenes through Cyclization of Propargylic Aryl Ethers

We describe here for the first time the synthesis of 2-(chalcogenyl)-3H-benzo­[f]­chromenes and the new 3-(phenylselanyl)-2H-chromenes by the radical or electrophilic cyclization of propargylic aryl ethers in the presence of diorganyl diselenides or ditellurides using Oxone as a green oxidant and ac...

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Published inJournal of organic chemistry Vol. 87; no. 22; pp. 15050 - 15060
Main Authors Hellwig, Paola S., Barcellos, Angelita M., Cargnelutti, Roberta, Barcellos, Thiago, Perin, Gelson
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 18.11.2022
Amer Chemical Soc
Subjects
Benzopyrans - chemistry
Chemistry
Chemistry, Organic
Cyclization
Ethers - chemistry
Molecular Structure
Physical Sciences
Science & Technology
ELECTROPHILIC CYCLIZATION
SELENIUM
CHROMENES
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Summary:We describe here for the first time the synthesis of 2-(chalcogenyl)-3H-benzo­[f]­chromenes and the new 3-(phenylselanyl)-2H-chromenes by the radical or electrophilic cyclization of propargylic aryl ethers in the presence of diorganyl diselenides or ditellurides using Oxone as a green oxidant and acetonitrile as solvent in a sealed tube at 100 °C. In this study, thirty-one chalcogenylchromenes with a broad substrate scope were prepared in moderate to excellent yields (50–98%), including compounds derived from natural products.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
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content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.2c01490