Methylsulfonic Acid Adsorbed on Silica Gel as a Solid Acid for Dimerization of Indoles: A Convenient Synthesis of 2,3′-Bi(3H-indol)-3-one Oximes

A simple, convenient, and efficient approach for the synthesis of (E)-2,3′-bi(3H-indol)-3-one oxime derivatives has been developed. The methodology is based on a three-component coupling reaction of indoles and sodium nitrite using a silica-supported methylsulfonic acid as solid acid. The practical...

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Bibliographic Details
Published inSynthetic communications Vol. 43; no. 21; pp. 2926 - 2935
Main Authors Chang, Qiong, Qu, Hongen, Qin, Wenbing, Liu, Liangxian, Chen, Zhengwang
Format Journal Article
LanguageEnglish
Published PHILADELPHIA Taylor & Francis Group 02.11.2013
Taylor & Francis
Taylor & Francis Ltd
Subjects
Biindoles
Chemistry
Chemistry, Organic
H-SiO
indoles
Physical Sciences
Science & Technology
tandem reaction
three-component coupling reaction
ALCOHOLS
tandem reaction
ALKENES
indoles
three-component coupling reaction
Biindoles
CATALYST
CH3SO3H-SiO2
BETA-DICARBONYL COMPOUNDS
EFFICIENT
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Summary:A simple, convenient, and efficient approach for the synthesis of (E)-2,3′-bi(3H-indol)-3-one oxime derivatives has been developed. The methodology is based on a three-component coupling reaction of indoles and sodium nitrite using a silica-supported methylsulfonic acid as solid acid. The practical utility of this three-component coupling reaction has been demonstrated in the gram-scale dimerization of indole. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications® for the following free supplemental resource: Full experimental and spectral details.]
ISSN:0039-7911
1532-2432
DOI:10.1080/00397911.2012.751611