Abstract
An efficient protocol for obtaining fused quinazolinones through an oxidative free-radical
cyclization under metal- and tin-free conditions is described. The oxidative cyclization
of various N -3-ω-iodoalkyl derivatives to provide tricyclic systems using dicumyl peroxide as
the sole reagent is studied. The method then is employed for the syntheses of 5-,
6-, and 7-membered fused quinazolinone analogues, including the natural products deoxyvasicinone
and mackinazolinone. A xanthate-based oxidative radical cascade addition/cyclization
process that allows the production of new menthol- and testosterone-quinazolinone
conjugates, as well as the first total synthesis of leucomidine C, are also reported.
Key words quinazolinone - free radicals - peroxides - xanthates - leucomidine C
