Direct C-H/C-H Coupling of the Azoloannulated Pteridines with Electron Rich (Hetero)Aromatic Compounds

Denis A Gazizov; Evgeny B Gorbunov; Ekaterina F Zhilina; Pavel A Slepukhin; Gennady L Rusinov

doi:10.1021/acs.joc.2c01558

Direct C-H/C-H Coupling of the Azoloannulated Pteridines with Electron Rich (Hetero)Aromatic Compounds

J Org Chem. 2022 Oct 7;87(19):13011-13022. doi: 10.1021/acs.joc.2c01558. Epub 2022 Sep 15.

Authors

Denis A Gazizov¹, Evgeny B Gorbunov¹, Ekaterina F Zhilina¹, Pavel A Slepukhin^{1

2}, Gennady L Rusinov^{1

2}

Affiliations

¹ Postovsky Institute of Organic Synthesis, Ural Branch of Russian Academy of Sciences, Sofia Kovalevskoy St. 22/20, Ekaterinburg 620108, Russia.
² Department of Organic and Biomolecular Chemistry, Ural Federal University, Mira St. 19, Ekaterinburg 620002, Russia.

PMID: 36107813
DOI: 10.1021/acs.joc.2c01558

Abstract

The methods for modification of azoloannulated pteridines with (hetero)aromatic nucleophiles using a nucleophilic substitution of hydrogen (S_N^H) methodology have been developed in this work. Stable intermediate σ^H-adducts, as well as products of an unexpected intramolecular rearrangement of diadducts, have been isolated and characterized. The potential of the proposed approach for obtaining donor-acceptor systems, in which the pteridine fragment of the molecule acts as an acceptor, was demonstrated. The main photophysical properties of the obtained D-A compounds have been studied.