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Synthesis 2012; 44(16): 2537-2546
DOI: 10.1055/s-0031-1290953
DOI: 10.1055/s-0031-1290953
special topic
Automated Multistep Continuous Flow Synthesis of 2-(1H-Indol-3-yl)thiazole Derivatives
Further Information
Publication History
Received: 01 March 2012
Accepted: 15 March 2012
Publication Date:
25 May 2012 (online)
Abstract
The multistep continuous flow assembly of 2-(1H-indol-3-yl)thiazoles using a Syrris AFRICA® synthesis station is reported. Sequential Hantzsch thiazole synthesis, deketalization, and Fischer indole synthesis provides rapid and efficient access to highly functionalized, pharmacologically significant 2-(1H-indol-3-yl)thiazoles. These complex drug-like small molecules are generated in reaction times of less than 15 minutes and in high yields (38–82% over three chemical steps without isolation of intermediates).
Key words
heterocycles - indoles - condensation - tandem reactions - microreactor - microfluidic synthesisSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis. Included are NMR spectra for final compounds and the structures of α-bromoketones 5a–l and hydrazines 10a–k.
- Supporting Information
-
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