STUDIES ON THE ALKYLATION OF QUINOLIN-2(1H)-ONE DERIVATIVES

Alkylation of quinolin-2(1H)-one (1) and its C(6) and C(7) substituted dervatives (OMe, OBn, and Cl) with 2-bromoacetophenone or chloroacetone under basic condition (K2CO3 in DMF) gave a mixture of N1- and O2- alkylated products with the former one as a major product. However, alkylation of 8-methoxy-, 8-benzyloxy-, and 8-chloro- quinolin-2(1H)-ones under the same reaction conditions gave exclusively O2-alkylated products.