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
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Organic chemistry frontiers
ISSN: 2052-4110 , E-ISSN: 2052-4129 |
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| Output data | Year: 2024, Volume: 11, Number: 2, Pages: 327-335 Pages count : 9 DOI: 10.1039/d3qo01690k | ||||
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Abstract:
[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.
Cite:
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 Scopus OpenAlex
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 Scopus OpenAlex
Identifiers:
| Scopus: | 2-s2.0-85178593860 |
| OpenAlex: | W4388845580 |