Automated Multistep Continuous Flow Synthesis of 2-(1H-Indol-3-yl)thiazole Derivatives

Synthesis (Stuttg). 2012;44(16):2537-2546. doi: 10.1055/s-0031-1290953.

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 min and in high yields (38%-82% over three chemical steps without isolation of intermediates).

Keywords: condensation; heterocycles; indoles; microfluidic synthesis; microreactors; tandem reaction.