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Synthesis 2014; 46(15): 2071-2078
DOI: 10.1055/s-0033-1338633
DOI: 10.1055/s-0033-1338633
paper
Trimethylsilyl Iodide as a Multifunctional Agent in the One-Pot Synthesis of 9-(1H-Indol-3-yl)xanthen-4-(9H)-ones from O-Methyl Protected Salicylaldehydes, Indoles, and β-Dicarbonyl Compounds
Further Information
Publication History
Received: 05 February 2014
Accepted after revision: 04 April 2014
Publication Date:
14 May 2014 (online)
Abstract
Trimethylsilyl iodide (TMSI) is introduced as an efficient reagent for the one-pot synthesis of 9-(1H-indol-3-yl)xanthen-4-(9H)-ones using the reaction of 2-methoxybenzaldehydes (as O-methyl protected salicylaldehydes), indoles, and β-dicarbonyl compounds. In this protocol, a set of TMSI reactions involving silylation, silyl enol ether formation, methyl deprotection, and nucleophilic substitution/cyclization are performed to furnish the target product. The key step in this protocol is the deprotection of the methoxy group by TMSI.
Supporting Information
- for this article is available online at http://www.thieme-connect.com/products/ejournals/journal/ 10.1055/s-00000084.
- Supporting Information
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