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A Synthetic Route to 2-Alkyl Indoles via Thiophenol-Mediated Ring-Opening of N-Tosylaziridines Followed by Copper Powder-Mediated C-N Cyclization/Aromatization

Masthanvali Sayyad, Yerramsetti Nanaji and Manas K. Ghorai*

*Department of Chemistry, Indian Institute of Technology, Kanpur 208016, India, Email: mkghoraiiitk.ac.in

M. Sayyad, Y. Nanaji, M. K. Ghorai, J. Org. Chem., 2015, 80, 12659-12667.

DOI: 10.1021/acs.joc.5b02251 (free Supporting Information)


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Abstract

A regioselective ring-opening of 2-(2-haloaryl)-3-alkyl-N-tosylaziridines with thiophenol, followed by copper powder-mediated intramolecular C-N cyclization and subsequent aromatization by the elimination of thiophenol enables the synthesis of indoles in good yields.

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Key Words

indoles


ID: J42-Y2015