Synthesis 2019; 51(11): 2371-2378
DOI: 10.1055/s-0037-1610696
paper
© Georg Thieme Verlag Stuttgart · New York

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

Rana Chatterjee
a   Department of Chemistry, Visva-Bharati (A Central University), Santiniketan 731235, India   Email: adinath.majee@visva-bharati.ac.in
,
b   Department of Organic and Biomolecular Chemistry, Chemical Engineering Institute, Ural Federal University, 19 Mira Street, 620002 Yekaterinburg, Russian Federation
,
Grigory V. Zyryanov
b   Department of Organic and Biomolecular Chemistry, Chemical Engineering Institute, Ural Federal University, 19 Mira Street, 620002 Yekaterinburg, Russian Federation
c   I. Ya. Postovskiy Institute of Organic Synthesis, Ural Division of the Russian Academy of Sciences, 22 S. Kovalevskoy Street, 620219 Yekaterinburg, Russian Federation
,
Adinath Majee*
a   Department of Chemistry, Visva-Bharati (A Central University), Santiniketan 731235, India   Email: adinath.majee@visva-bharati.ac.in
› Author Affiliations
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.

Supporting Information

 
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