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

The methods for modification of azoloannulated pteridines with (hetero)­aromatic nucleophiles using a nucleophilic substitution of hydrogen (SN H) methodology have been developed in this work. Stable intermediate σH-adducts, as well as products of an unexpected intramolecular rearrangement of diaddu...

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Bibliographic Details
Published in:Journal of organic chemistry 2022-10, Vol.87 (19), p.13011-13022
Main Authors: Gazizov, Denis A., Gorbunov, Evgeny B., Zhilina, Ekaterina F., Slepukhin, Pavel A., Rusinov, Gennady L.
Format: Article
Language:English
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Summary:The methods for modification of azoloannulated pteridines with (hetero)­aromatic nucleophiles using a nucleophilic substitution of hydrogen (SN H) methodology have been developed in this work. Stable intermediate σH-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.
ISSN:0022-3263
1520-6904
DOI:10.1021/acs.joc.2c01558