Synthesis 2018; 50(12): 2423-2431
DOI: 10.1055/s-0037-1609482
paper
© Georg Thieme Verlag Stuttgart · New York

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

a   Department of Organic and Biomolecular Chemistry, Ural Federal University, Mira 19, 620002 Ekaterinburg, Russian Federation   Email: i.a.khalymbadzha@urfu.ru
,
Ramil F. Fatykhov
a   Department of Organic and Biomolecular Chemistry, Ural Federal University, Mira 19, 620002 Ekaterinburg, Russian Federation   Email: i.a.khalymbadzha@urfu.ru
,
Oleg N. Chupakhin
a   Department of Organic and Biomolecular Chemistry, Ural Federal University, Mira 19, 620002 Ekaterinburg, Russian Federation   Email: i.a.khalymbadzha@urfu.ru
b   Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, Kovalevskoy 22, 620219 Ekaterinburg, Russian Federation
,
Valery N. Charushin
a   Department of Organic and Biomolecular Chemistry, Ural Federal University, Mira 19, 620002 Ekaterinburg, Russian Federation   Email: i.a.khalymbadzha@urfu.ru
b   Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, Kovalevskoy 22, 620219 Ekaterinburg, Russian Federation
,
Tatiana A. Tseitler
a   Department of Organic and Biomolecular Chemistry, Ural Federal University, Mira 19, 620002 Ekaterinburg, Russian Federation   Email: i.a.khalymbadzha@urfu.ru
,
Ainur D. Sharapov
a   Department of Organic and Biomolecular Chemistry, Ural Federal University, Mira 19, 620002 Ekaterinburg, Russian Federation   Email: i.a.khalymbadzha@urfu.ru
,
Anna K. Inytina
a   Department of Organic and Biomolecular Chemistry, Ural Federal University, Mira 19, 620002 Ekaterinburg, Russian Federation   Email: i.a.khalymbadzha@urfu.ru
,
Victor G. Kartsev
c   InterBioScreen Ltd., Institutsky Prospect 7a, 142432 Chernogolovka, Russian Federation
› Author Affiliations
This research was financially supported by the Ministry of Education of the Russian Federation (Project 4.6351.2017/8.9) and the Russian Science Foundation (Ref. # 14–13–01177).
Further Information

Publication History

Received: 28 February 2018

Accepted after revision: 16 March 2018

Publication Date:
24 April 2018 (online)


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.

Supporting Information

 
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