Electrochemical Synthesis of 3-(Sulfonyl)quinol-4-ones from o-Alkynyl-N-(formyl)anilides and Sulfinates

Electrolysis of o-alkynyl-N-(formyl)anilides and sodium sulfinates on graphite electrodes delivers biologically sound 3-(sulfonyl)quinol-4-ones with moderate to good yields. The reaction is carried out in an undivided cell in the presence of silver(I) oxide with potassium iodide or sodium tetrafluoroborate as the supporting electrolyte. The reaction tolerates variously substituted anilides as well as aryl and alkyl sulfinates. The transformation proceeds as a domino sequence of oxysulfonylation and cyclocondensation steps. © 2024 American Chemical Society.

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Authors
Bondarev V.L. , Festa A.A. , Storozhenko O.A. , Kokorekin V.A. , Novikov A.P. , Varlamov A.V. , Voskressensky L.G.
Journal
Organic Letters
Language
English
Status
Published
Link
External link
DOI
10.1021/ACS.ORGLETT.4C04209
Year
2024
Organizations
  • 1 Organic Chemistry Department, Science Faculty, Patrice Lumumba Peoples’ Friendship University of Russia, RUDN University, Miklukho-Maklaya strasse, 6, Moscow, 117198, Russian Federation
  • 2 Sechenov First Moscow State Medical University, Trubetskaya strasse 8−2, Moscow, 119991, Russian Federation
  • 3 Frumkin Institute of Physical Chemistry and Electrochemistry, Russian Academy of Sciences, Leninsky prospect, 31 Building 4, Moscow, 119071, Russian Federation
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