銅催化分子內碳-氮鍵偶合反應 : 吲哚酮及菲啶酮的合成

淡江大學機構典藏 > 理學院 > 化學學系暨研究所 > 學位論文 > Item 987654321/93975

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题名:	銅催化分子內碳-氮鍵偶合反應 : 吲哚酮及菲啶酮的合成
其它题名:	Copper-catalyzed intramolecular c-n coupling reaction for the synthesis of oxindoles and phenanthridinones
作者:	詹于慧;Jhan, Yu-Huei
贡献者:	淡江大學化學學系碩士班謝仁傑;Hsieh, Jen-Chieh
关键词:	Ullmann反應;串聯反應;螺-吲哚酮;菲啶酮;Ullmann Reaction;Domino Reaction;spiro-oxindoles;phenanthridinones
日期:	2013
上传时间:	2014-01-23 13:45:02 (UTC+8)
摘要:	第一部分: 利用不同方法合成3,3 spiro-oxindole結構的產物並探討反應機構之差異。第二部份: 利用高效率銅催化分子內形成碳-氮鍵，利用起始物鄰溴苯乙醯胺在少量的氧化亞銅和鄰苯二胺空氣中可合成具有高產率的3,3 spiro-oxindole衍生物結構。第三部分：利用高效率銅催化分子內形成碳-氮鍵，利用起始物2’-bromo-2-cyanodipheny在少量的碘化銅和氫氧化鈉在100℃下可合成具高產率的菲啶酮衍生物結構。 The 1st Part: Variously synthetic methods of 3,3 spiro-oxindole derivatives were carried out and comparison of the mechanisms for different pathway was discussed. The 2st Part: An efficient copper-catalyzed intramolecular N-arylation was carried out by involving 2,2-substituted 2-(2-bromoaryl)acetamide to afford various substituted oxindoles with a small amount of Cu2O and benzene-1,2-diamine as catalytic system under aerobic conditions, which provided good to excellent yields with tolerance of wide variety of substrates. The 3st Part: An efficient copper-catalyzed intramolecular N-arylation was carried out by involving 2’-bromo-2-cyanodipheny to afford variously substituted phenanthridinones with a small amount of CuI and Sodium hydroxide at 100 oC, which provided good to excellent yields with tolerance of wide variety of substrates.
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