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Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
Published on: July 17, 2020
Photocatalytic Iminyl Radical Cyclization for the Synthesis of Quinazolinones
Neissa Usanase1, Jensen L Rocha1, Joyce J Yoo1
1Department of Chemistry and Biochemistry, Washington and Lee University, Lexington, Virginia24450, United States.
Abstract:
An operationally simple protocol for the synthesis of medicinally relevant quinazolin-4(3H)-ones is described. This method employs an organic dye, ambient atmosphere, and visible light to activate α-azido benzamides through a photoinduced hydrogen atom transfer, generating iminyl radicals upon extrusion of dinitrogen. Cyclization to close the pyrimidinone ring then affords a variety of quinazolinone derivatives. This photocatalytic strategy establishes a foundation for iminyl radical-mediated heterocycle synthesis from alkyl azides under mild conditions.
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