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Quinazolinones/Benzothiadiazines as Amidyl/Aminyl Radical Precursors for Controlled Cascade Cyclization via Photocatalyzed PCET.

Mandapati Bhargava ReddyKesavan PrasanthNalladhambi NeerathilingamRamasamy Anandhan
Published in: Organic letters (2022)
Quinazolinones/benzothiadiazines were used as amidyl/aminyl radical precursors for cascade cyclizations via a photoredox-catalyzed proton-coupled electron transfer (PCET) process for the first time. A controlled synthesis of isoindole-fused quinazolinones/benzothiadiazines was carried out via quinazolinone amidyl/benzothiadiazine aminyl radical addition to the C-C triple bond under mild conditions. This transition-metal-free method provides an efficient and broad substrate scope for the synthesis of isoindole-fused quinazolinones/benzothiadiazines with step economy and atom efficiency.
Keyphrases
  • electron transfer
  • amino acid
  • structural basis
  • solid state