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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

Alexander V. Shchepochkin  ∗
a   Institute of Organic Synthesis of the Russian Academy of Sciences, 22 S. Kovalevskoy Street, 620990 Ekaterinburg, Russian Federation
,
Oleg N. Chupakhin 
a   Institute of Organic Synthesis of the Russian Academy of Sciences, 22 S. Kovalevskoy Street, 620990 Ekaterinburg, Russian Federation
,
Nadezhda S. Demina 
a   Institute of Organic Synthesis of the Russian Academy of Sciences, 22 S. Kovalevskoy Street, 620990 Ekaterinburg, Russian Federation
,
Maxim A. Averkov 
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
,
Pavel A. Slepukhin 
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
,
Anton A. Telezhkin 
b   A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky St., Irkutsk 664033, Russian Federation
,
Boris A. Trofimov 
b   A.E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch of the Russian Academy of Sciences, 1 Favorsky St., Irkutsk 664033, Russian Federation
,
Valery N. Charushin 
a   Institute of Organic Synthesis of the Russian Academy of Sciences, 22 S. Kovalevskoy Street, 620990 Ekaterinburg, Russian Federation
› Author AffiliationsThe 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).
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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.

Key words

electrochemical phosphorylation - anodic oxidation - C–H functionalization - green chemistry - acridine

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1521-3166.
  • Supporting Information


Publication History

Received: 01 March 2021

Accepted after revision: 31 May 2021

Accepted Manuscript online:
31 May 2021

Article published online:
21 June 2021

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