New Tool for Heterocycle Functionalization

  • Author: Melania Tesio
  • Published: 16 December 2012
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
  • Source / Publisher: Nature/Nature Publishing Group
thumbnail image: New Tool for Heterocycle Functionalization

Heterocycles, molecules containing a ring where at least one atom is not a carbon, play important roles in medicinal chemistry as they constitute a wide range of drugs. Yuta Fujiwara, Scripps Research Institute, USA, and colleagues demonstrated that ten different zinc bis(alkanesulphinate) salts can be used as a chemical toolkit to incorporate diverse chemical groups into heterocycles and, thus, generate novel chemical compounds for drug discovery.

Zinc bis(alkanesulphinate) salts reacted at heterocycles’ carbon-hydrogen bonds, transforming them into carbon-carbon bonds by attaching the alkyl group of the salts. This conversion produced novel heterocycles bearing pharmaceutically important groups such as the fluoroalkyl group, required to improve the half-life of drugs. The reaction, moreover, could proceed in different solutes (organic solvents, water, cellular fluids), it did not induce substrate decomposition, and it could be sequentially performed.

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