Synthesis of New Phenothiazine/3-cyanoquinoline and Phenothiazine/3-aminothieno[2,3-b]pyridine(-quinoline) Heterodimers.

ABSTRACT: The aim of this work was to prepare new heterodimeric molecules containing pharmacophoric fragments of 3-cyanoquinoline/3-aminothieno[2,3-b]pyridine/3-aminothieno[2,3-b]quinoline on one side and phenothiazine on the other. The products were synthesized via selective S-alkylation of readily available 2-thioxo-3-cyanopyridines or -quinolines with N-(chloroacetyl)phenothiazines, followed by base-promoted Thorpe-Ziegler isomerization of the resulting N-[(3-cyanopyridin-2-ylthio)acetyl]phenothiazines. We found that both the S-alkylation and the Thorpe-Ziegler cyclization reactions, when conducted with KOH under heating, were accompanied to a significant extent by a side reaction involving the elimination of phenothiazine. Optimization of the conditions (0-5 °C, anhydrous N,N-dimethylacetamide a

SUBMITTER: Dotsenko VV 

PROVIDER: S-EPMC12524799 | biostudies-literature | 2025 Oct

REPOSITORIES: biostudies-literature