Electrochemical synthesis of CN-substituted imidazo[1,5-a]pyridines via cascade process using NH4SCN as both electrolyte and non-trivial cyanating agent

Electrochemical synthesis of CN-substituted imidazo[1,5-a]pyridines via cascade process using NH4SCN as both electrolyte and non-trivial cyanating agent Full article

Journal

Organic chemistry frontiers
ISSN: 2052-4110 , E-ISSN: 2052-4129

Output data

Year: 2024, Volume: 11, Number: 2, Pages: 327-335 Pages count : 9 DOI: 10.1039/d3qo01690k

Authors

Grishin Sergei S. ^1,2 , Mulina Olga Mikhailovna ² , Vil' Vera A. ² , Terent'ev Alexander Olegovich ^1,2

Affiliations

1	Mendeleev University of Chemical Technology of Russia, 9 Miusskaya Square, 125047, Moscow, Russian Federation
2	Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky Prospect, Moscow, 119991, Russian Federation

[CN] species were generated in the course of electrochemical oxidation of SCN anions and used in the three-component electrosynthesis of 1-cyano-imidazo[1,5-a]pyridines from pyridine-2-carboxaldehydes, amines, and NH4SCN. In contrast to previously known electrochemical methods, NH4SCN acts as a CN source rather than a SCN source. A variety of 1-cyano-imidazo[1,5-a]pyridines were obtained in good yields under constant current conditions in an undivided electrochemical cell. The electrosynthesis presumably involves the generation of a cyanating reagent, its addition to the C[double bond, length as m-dash]N bond of the imine, formed from pyridine-2-carboxaldehyde and amine, followed by a cascade of DMSO-mediated or Shono-type anodic oxidation and cyclization. The leading 1-cyano-imidazo[1,5-a]pyridines exhibit better antifungal activity against Venturia inaequalis, Rhizoctonia solani, and Bipolaris sorokiniana than the commercial fungicide triadimefon.

Grishin S.S. , Mulina O.M. , Vil' V.A. , Terent'ev A.O.
Electrochemical synthesis of CN-substituted imidazo[1,5-a]pyridines via cascade process using NH4SCN as both electrolyte and non-trivial cyanating agent
Organic chemistry frontiers. 2024. V.11. N2. P.327-335. DOI: 10.1039/d3qo01690k WOS Scopus OpenAlex

Web of science:	WOS:001114838900001
Scopus:	2-s2.0-85178593860
OpenAlex:	W4388845580

DB	Citing
OpenAlex	4
Scopus	3
Web of science	6