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

Sayyad, Masthanvali ; Nanaji, Yerramsetti ; Ghorai, Manas K. (2015) A Synthetic Route to 2-Alkyl Indoles via Thiophenol-Mediated Ring-Opening of N-Tosylaziridines Followed by Copper Powder-Mediated C–N Cyclization/Aromatization Journal of Organic Chemistry, 80 (24). pp. 12659-12667. ISSN 0022-3263

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Official URL: http://doi.org/10.1021/acs.joc.5b02251

Related URL: http://dx.doi.org/10.1021/acs.joc.5b02251

Abstract

A simple strategy for the syntheses of 2-alkyl indoles via 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, with good yields is described. Utilizing this protocol, 2-carboxyindole has been synthesized easily.

Item Type:Article
Source:Copyright of this article belongs to American Chemical Society.
ID Code:117267
Deposited On:15 Apr 2021 10:36
Last Modified:15 Apr 2021 10:36

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