Nucleophilic Addition/Electrocyclization Strategy toward Polyheterocyclic-Fused Quinoline-2-thiones in Green Solvent

J Org Chem. 2022 Oct 7;87(19):13300-13307. doi: 10.1021/acs.joc.2c00893. Epub 2022 Sep 12.

Abstract

A metal-free and base-free cyclization reaction of ortho-heteroaryl anilines with isothiocyanatobenzene for the synthesis of diverse polyheterocyclic-fused quinoline-2-thiones was developed in PEG-200. This protocol features green solvent, lack of requirement for a metal and base, short reaction time consumption, and facile isolation via simple filtration. Furthermore, this protocol is easy to scale up which demonstrates outstanding synthetic scalability.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Aniline Compounds
  • Catalysis
  • Quinolines*
  • Solvents
  • Thiones*

Substances

  • Aniline Compounds
  • Quinolines
  • Solvents
  • Thiones