Regioselective Synthesis of Benzazetines and Indoles from Alkenylanilides and Dimethyl(methylthio)sulfonium Trifluoromethanesulfonate

• Kentaro Okuma

  Department of Chemistry, Faculty of Science, Fukuoka University

• Itsuki Takeshita

  Department of Chemistry, Faculty of Science, Fukuoka University

• Takumi Yasuda

  Department of Chemistry, Faculty of Science, Fukuoka University

• Kosei Shioji

  Department of Chemistry, Faculty of Science, Fukuoka University

Abstract

Regioselective synthesis of benzazetines and indoles from o-alkenylanilides was achieved. The reaction of o-vinylbenzanilide with dimethyl(methylthio)sulfonium trifluoromethanesulfonate (DMTST) gave the corresponding benzazetine in 92% yield, whereas the reaction of o-vinyl-N-p-toluenesulfonylanilide gave N-tosylindoline in 77% yield. 3-Methy-N-p-tosylindole was directly synthesized by the reaction of o-isopropenyl-N-p-tosylanilide with dimethyl disulfide and methyl triflate in 85% yield.

Journal

• Chemistry Letters

  Chemistry Letters 35 (10), 1122-1123, 2006-09-09

  Oxford University Press (OUP)

Keywords

• General Chemistry

Details

• CRID: 1360846644040883072
• NII Article ID: 10018322974
• NII Book ID: AA00603318
• DOI: 10.1246/cl.2006.1122
• ISSN: 13480715
• ISSN: 03667022
• Web Site: https://academic.oup.com/chemlett/article-pdf/35/10/1122/55590910/cl.2006.1122.pdf
• Data Source:
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  • CiNii Articles