Synthesis of Heteroannulated Indolopyrazines through Domino N-H Palladium-Catalyzed/Metal-Free Oxidative C-H Bond Activation

Yuriy A Kvashnin; Egor V Verbitskiy; Ekaterina F Zhilina; Gennady L Rusinov; Oleg N Chupakhin; Valery N Charushin

doi:10.1021/acsomega.0c01945

Synthesis of Heteroannulated Indolopyrazines through Domino N-H Palladium-Catalyzed/Metal-Free Oxidative C-H Bond Activation

ACS Omega. 2020 Jun 18;5(25):15681-15690. doi: 10.1021/acsomega.0c01945. eCollection 2020 Jun 30.

Authors

Yuriy A Kvashnin¹, Egor V Verbitskiy^{1

2}, Ekaterina F Zhilina¹, Gennady L Rusinov^{1

2}, Oleg N Chupakhin^{1

2}, Valery N Charushin^{1

2}

Affiliations

¹ I. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, S. Kovalevskaya Str., 22, Ekaterinburg 620108, Russia.
² Ural Federal University, Mira St. 19, Ekaterinburg 620002, Russia.

Abstract

A convenient approach to [1,2,5]oxadiazolo[3',4':5,6]pyrazino[2,3-b]indoles and their heteroannulated analogues bearing various aryl substituents in the backbone has been developed. This synthetic protocol is based on Pd-catalyzed Buchwald-Hartwig and subsequent annulation by intramolecular oxidative cyclodehydrogenation. The photophysical properties for new polycycles have been measured.