Hydrogen-Bond-Catalyzed Arylationof 3-(Aminoalkyl)indoles via C-N Bond Cleavage with Thiourea under Microwave Irradiation: An Approach to 3-(α,α-Diarylmethyl) indoles

被引：24
|
作者：
Deb, Mohit L. [1 ]
Das, Churnika [1 ]
Deka, Bhaskar [1 ]
Saikia, Prakash J. [2 ]
Baruah, Pranjal K. [1 ]
机构：
[1] Gauhati Univ, Dept Appl Sci, GUIST, Gauhati 781014, Assam, India
[2] Analyt Chem Div CSIR NEIST, Jorhat 785006, Assam, India
来源：
SYNLETT | 2016年 / 27卷 / 20期
关键词：
hydrogen-bond-catalyzed; thiourea; microwave; indoles; vinylogous iminium ion; 3-AMINO ALKYLATED INDOLES; MANNICH-TYPE REACTION; MULTICOMPONENT SYNTHESIS; ANTIOXIDANT ACTIVITIES; MICHAEL ADDITION; DERIVATIVES; CHEMISTRY;
D O I：
10.1055/s-0036-1588887
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
We have developed a simple and efficient method for the arylation of 3-(aminoalkyl) indoles with aryl alcohols and other aromatic nucleophiles through C-N bond cleavage under microwave irradiation to synthesize 3-(alpha, alpha-diarylmethyl) indoles. The method uses thiourea as catalyst, which is environmentally benign, water-tolerant and easy to handle. Notably, acid-sensitive substrates are tolerated under the reaction conditions. Thiourea activates the tertiary amine through double hydrogen bonding and converts it into a better leaving group. The reaction proceeds through the formation of vinylogous iminium ion as an intermediate.
引用
收藏
页码：2788 / 2794
页数：7
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