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

• DOI: 10.1055/s-0028-1083505
• Publication Date: 2008-10-11T00:41:45Z
• Authors: Wei-Min Dai; Jianyu Shi; Jinlong Wu
• Keywords: Moiety; Heck Reaction; Ugi reaction; Component (thermodynamics)

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