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Synthesis 2019; 51(11): 2371-2378
DOI: 10.1055/s-0037-1610696
DOI: 10.1055/s-0037-1610696
paper
Vinylation of Carbonyl Oxygen in 4-Hydroxycoumarin: Synthesis of Heteroarylated Vinyl Ethers
A. Majee acknowledges the DST-RSF Major Research Project (Ref. No. INT/RUS/RSF/P-08) for financial support. S. Santra acknowledges the financial support from the Russian Science Foundation – Russia (Ref. # 18-73-00301).Further Information
Publication History
Received: 07 January 2019
Accepted after revision: 28 January 2019
Publication Date:
07 March 2019 (online)
Abstract
The unique nucleophilic character of the carbonyl oxygen of 4-hydroxy coumarin has been observed by the BF3·OEt2 catalyzed reaction of 4-hydroxycoumarin and alkynes. The reactions of 4-hydroxycoumarin and substituted 4-hydroxycoumarin with various terminal alkynes have been studied. In case of internal alkyne (prop-1-yn-1-ylbenzene), the reaction with 4-hydroxycoumarin led to the corresponding product with an E/Z ratio of 3:1. This protocol is operationally very simple and has much potential for the synthesis of heteroarylated vinyl ethers from basic chemicals.
Key words
2-(vinyloxy)-4H-chromen-4-one - O-vinylation - 4-hydroxy coumarin - alkynes - solvent-freeSupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610696.
- Supporting Information
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