Synthesis 2021; 53(20): 3791-3798
DOI: 10.1055/a-1521-3166
paper

Electrochemical Aromatization of Dihydroazines: Effect of Chalco­genophosphoryl (CGP) Substituents on Anodic Oxidation of 9-CGP-9,10-dihydroacridine

a   Institute of Organic Synthesis of the Russian Academy of Sciences, 22 S. Kovalevskoy Street, 620990 Ekaterinburg, Russian Federation
,
a   Institute of Organic Synthesis of the Russian Academy of Sciences, 22 S. Kovalevskoy Street, 620990 Ekaterinburg, Russian Federation
,
a   Institute of Organic Synthesis of the Russian Academy of Sciences, 22 S. Kovalevskoy Street, 620990 Ekaterinburg, Russian Federation
,
a   Institute of Organic Synthesis of the Russian Academy of Sciences, 22 S. Kovalevskoy Street, 620990 Ekaterinburg, Russian Federation
,
Tatyana Yu. Shimanovskaya
a   Institute of Organic Synthesis of the Russian Academy of Sciences, 22 S. Kovalevskoy Street, 620990 Ekaterinburg, Russian Federation
,
a   Institute of Organic Synthesis of the Russian Academy of Sciences, 22 S. Kovalevskoy Street, 620990 Ekaterinburg, Russian Federation
,
Pavel A. Volkov
b   A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky St., Irkutsk 664033, Russian Federation
,
b   A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky St., Irkutsk 664033, Russian Federation
,
b   A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky St., Irkutsk 664033, Russian Federation
,
a   Institute of Organic Synthesis of the Russian Academy of Sciences, 22 S. Kovalevskoy Street, 620990 Ekaterinburg, Russian Federation
› Institutsangaben
The research was financially supported by the Russian Foundation for Basic Research (research project No. 19-29-08037). P.V. and A.T. thank the Russian Science Foundation for the financial support (Grant No. 18-73-10080).


Abstract

The effect of chalcogenophosphoryl fragments on the anodic oxidation of 9-chalcogenophosphoryl-9,10-dihydroacridines was studied in detail. The data of X-ray structural analyses, quantum chemical calculations, and cyclic voltammetry measurements obtained for these compounds provide an explanation of the observed features. The direct electrochemical phosphorylation of acridine was first carried out successfully.

Supporting Information



Publikationsverlauf

Eingereicht: 01. März 2021

Angenommen nach Revision: 31. Mai 2021

Accepted Manuscript online:
31. Mai 2021

Artikel online veröffentlicht:
21. Juni 2021

© 2021. Thieme. All rights reserved

Georg Thieme Verlag KG
Rüdigerstraße 14, 70469 Stuttgart, Germany