Synthesis of 3-Arylideneindolin-2-ones from 2-Aminophenols by Ugi Four-Component Reaction and Heck Carbocyclization

2-Aminophenols underwent the Ugi four-component reaction (U-4CR) with trans-cinnamic acids, aromatic aldehydes and isocyanides in MeOH (50 degrees C, 48 h) to give the linear alpha-[N-(2-hydroxyphenyl)-substituted amido] carboxamides in 54-80% yields. Treatment of the 2-hydroxyphenyl moiety in the U-4CR products with NaH and PhNTf2 afforded the corresponding aryl triflates (77-100%), which were subjected to the intramolecular Heck reaction (IMHR) catalyzed by 3-5 mol% Pd(OAc)(2)-BINAP (MeCN, 180 degrees C, 30-60 min) under microwave heating to furnish alpha-(3-arylidene-2-oxindol-1-yl) carboxamides in 52-77% yields.