Thioarylation of anilines using dual catalysis: two-step synthesis of phenothiazines
Amy C. Dodds, Sabrina Puddu, Andrew Sutherland
Abstract
-thioarylation reaction of various protected aniline derivatives and less reactive, unprotected analogues. The thioarylated adducts were then cyclised to the desired phenothiazines using either an Ullmann-Goldberg or Buchwald-Hartwig coupling reaction. The dual catalytic thioarylation and copper(I)-catalysed cyclisation approach was used for the four-step synthesis of methopromazine, a neuroleptic agent with antipsychotic activity.
Topics & Concepts
ChemistryDual (grammatical number)Combinatorial chemistryCatalysisMedicinal chemistryStereochemistryOrganic chemistryLiteratureArtPhenothiazines and Benzothiazines Synthesis and ActivitiesSynthesis and Reactivity of HeterocyclesCatalytic C–H Functionalization Methods