Synthesis of 3-Arylideneindolin-2-ones from 2-Aminophenols by Ugi Four-Component Reaction and Heck Carbocyclization
Synthesis of 3-Arylideneindolin-2-ones from 2-Aminophenols by Ugi Four-Component Reaction and Heck Carbocyclization
复制标题
Ugi四组分反应和Heck碳环化从2-氨基酚合成3-亚芳基吲哚啉-2-酮
DOI：
10.1055/s-0028-1083505
复制
发表时间：
2008-10-21
期刊：
影响因子：
2
通讯作者：
Wu, Jinlong
中科院分区：
文献类型：
--
作者：
Dai, Wei-Min;Shi, Jianyu;Wu, Jinlong
2-氨基酚与反式肉桂酸、芳香醛和异氰酸酯在甲醇中（50℃，48 h）进行Ugi四组分反应（U-4CR），得到线性α -[N-（2-羟基苯基）取代胺]羧酰胺，收率为54-80%。用NaH和PhNTf2处理U-4CR产物中的2-羟基苯基部分，得到相应的芳基三氟酸酯（77-100%），然后用3-5摩尔% Pd(OAc)(2)- binap （MeCN, 180℃，30-60 min）在微波加热下进行分子内Heck反应（IMHR），得到产率为52-77%的α -（3-芳基-2-氧吲哚-1-基）羧酰胺。
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.