Radical cyclizations to quinolone and isoquinolone systems under oxidative and reductive conditions

Radical cyclizations to quinolone and isoquinolone systems under Fenton-type and n-Bu3SnH-mediated conditions are described. For N-iodoalkylquinolones, ca. 3:1 mixtures of oxidative cyclization products at C-2, and unexpectedly at C-8, were obtained under both conditions. Five- or six-membered oxidative cyclization products were obtained from N-iodoalkylisoquinolones under Fenton-type conditions, whereas n-Bu3SnH-mediated reactions gave products of reductive cyclization in the five, six, and seven-membered series.