Synthesis and cyclisation studies of (E)-2-aryl-1-methy1-3-styrylquinolin-4(1H)-ones

The synthesis of (E)-2-ary1-1-methy1-3-styrylquinolin-4(1H)-ones, through the Heck reaction of 2-ary1-3-iodo-l-methyl-quinolin-4(1H)-ones with styrene is described. 2-Ary1-3-iodo-1-methy1-2-quinolin-4(1H)-ones can be obtained efficiently in a two-step transformation, methylation followed by in situ cyclization of N-(2-acetylphenyl)benzamides into 2-aryl-1-methylquinolin-4(1H)-ones, which underwent selective 3-iodination with iodine and a catalytic amount of Can. Cyclisation studies of (E)-2-ary1-1-methy1-3-styrylquinolin-4(1H)-ones under high temperature or photoinduced electrocyclisation lead to 4-aryl-2-phenylfuro[3,2-c]quinolines and 12-methyl-5-phenylbenzo[c]acridin-7(12H)-ones. (C) 2015 Elsevier Ltd. All rights reserved.