Vinylation of Carbonyl Oxygen in 4-Hydroxycoumarin: Synthesis of Heteroarylated Vinyl Ethers

Rana Chatterjee; Sougata Santra; Grigory V. Zyryanov; Adinath Majee

doi:10.1055/s-0037-1610696

Synthesis, Inhaltsverzeichnis

Synthesis 2019; 51(11): 2371-2378
DOI: 10.1055/s-0037-1610696

paper

Vinylation of Carbonyl Oxygen in 4-Hydroxycoumarin: Synthesis of Heteroarylated Vinyl Ethers

Rana Chatterjee

^aDepartment of Chemistry, Visva-Bharati (A Central University), Santiniketan 731235, India eMail: adinath.majee@visva-bharati.ac.in

,

Sougata Santra

^bDepartment of Organic and Biomolecular Chemistry, Chemical Engineering Institute, Ural Federal University, 19 Mira Street, 620002 Yekaterinburg, Russian Federation

,

Grigory V. Zyryanov

^bDepartment of Organic and Biomolecular Chemistry, Chemical Engineering Institute, Ural Federal University, 19 Mira Street, 620002 Yekaterinburg, Russian Federation

^cI. Ya. Postovskiy Institute of Organic Synthesis, Ural Division of the Russian Academy of Sciences, 22 S. Kovalevskoy Street, 620219 Yekaterinburg, Russian Federation

,

Adinath Majee*

^aDepartment of Chemistry, Visva-Bharati (A Central University), Santiniketan 731235, India eMail: adinath.majee@visva-bharati.ac.in

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Abstract

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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-free

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References

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