Synthesis of cyclobuta[c]quinolin-3-ones. Intra- and inter-molecular photocycloadditions of 4-alkoxy-2-quinolone systems with olefins
Abstract
Irradiation of 4-allyloxy-2-quinolone (1) gave the tetracyclic adduct (2) as the sole product, whereas 4-(but-3-enyloxy)-2-quinolone (7) led to a mixture (ca. 7 : 1) of adducts (8) and (9); base treatment of the adducts (2), (8), and (9) gave rise to the novel 1,2-dihydrocyclobuta[c]quinolin-3(4H)ones (3), (10), and (11) in quantitative yields.