Transition-Metal-Free С–С Coupling of 5,7-Dihydroxybenzopyrones with Quinoxalones and Pteridinones

Igor A. Khalymbadzha; Ramil F. Fatykhov; Oleg N. Chupakhin; Valery N. Charushin; Tatiana A. Tseitler; Ainur D. Sharapov; Anna K. Inytina; Victor G. Kartsev

doi:10.1055/s-0037-1609482

Synthesis, Table of Contents

Synthesis 2018; 50(12): 2423-2431
DOI: 10.1055/s-0037-1609482

paper

Transition-Metal-Free С–С Coupling of 5,7-Dihydroxybenzopyrones with Quinoxalones and Pteridinones

Igor A. Khalymbadzha *

^aDepartment of Organic and Biomolecular Chemistry, Ural Federal University, Mira 19, 620002 Ekaterinburg, Russian Federation Email: i.a.khalymbadzha@urfu.ru

,

Ramil F. Fatykhov

^aDepartment of Organic and Biomolecular Chemistry, Ural Federal University, Mira 19, 620002 Ekaterinburg, Russian Federation Email: i.a.khalymbadzha@urfu.ru

,

Oleg N. Chupakhin

^aDepartment of Organic and Biomolecular Chemistry, Ural Federal University, Mira 19, 620002 Ekaterinburg, Russian Federation Email: i.a.khalymbadzha@urfu.ru

^bInstitute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, Kovalevskoy 22, 620219 Ekaterinburg, Russian Federation

,

Valery N. Charushin

^aDepartment of Organic and Biomolecular Chemistry, Ural Federal University, Mira 19, 620002 Ekaterinburg, Russian Federation Email: i.a.khalymbadzha@urfu.ru

^bInstitute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, Kovalevskoy 22, 620219 Ekaterinburg, Russian Federation

,

Tatiana A. Tseitler

^aDepartment of Organic and Biomolecular Chemistry, Ural Federal University, Mira 19, 620002 Ekaterinburg, Russian Federation Email: i.a.khalymbadzha@urfu.ru

,

Ainur D. Sharapov

^aDepartment of Organic and Biomolecular Chemistry, Ural Federal University, Mira 19, 620002 Ekaterinburg, Russian Federation Email: i.a.khalymbadzha@urfu.ru

,

Anna K. Inytina

^aDepartment of Organic and Biomolecular Chemistry, Ural Federal University, Mira 19, 620002 Ekaterinburg, Russian Federation Email: i.a.khalymbadzha@urfu.ru

,

Victor G. Kartsev

^cInterBioScreen Ltd., Institutsky Prospect 7a, 142432 Chernogolovka, Russian Federation

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Abstract

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Abstract

A new synthetic protocol for nucleophilic substitution of hydrogen in quinoxalones and pteridinones by the action of 5,7-dihydroxycoumarins and related m-dihydroxybenzene compounds has been developed. The C–C coupling reaction proved to proceed smoothly under rather mild conditions, thus giving the corresponding C–H functionalized products in good yields. The advantages of this environmentally benign protocol are high regio- and chemoselectivity, and an easy workup procedure. Direct incorporation of the coumarin moiety into the pyrazine ring in pteridines or quinoxalines provides a short pathway to pyrazine-coumarin hybrid compounds.

Key words

metal-free coupling - halogen-free coupling - pteridines - quinoxalines - C–H arylation - substitution of hydrogen

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References

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