REACTION OF 1-SUBSTITUTED 3-(2-HYDROXYETHYLAMINO)QUINOLINE-2,4(1<i>H</i>,3<i>H</i>)-DIONES WITH ISOTHIOCYANIC ACID

Authors

  • Antonín Klásek Department of Chemistry, Faculty of Technology, Tomas Bata University, CZ-76272 Zlín
  • Antonín Lyčka Research Institute for Organic Syntheses (VUOS), CZ-533 54 Pardubice
  • Michal Rouchal Department of Chemistry, Faculty of Technology, Tomas Bata University, CZ-76272 Zlín
  • Radek Bartošík Department of Chemistry, Faculty of Technology, Tomas Bata University, CZ-76272 Zlín

DOI:

https://doi.org/10.1007/5443

Keywords:

isocyanic acid, isothiocyanic acid, 2-thioxo-1H-imidazo[4, 5-c]quinolin-4(2H)-ones, 5-c]quinolin-4(5H)-ones, quinoline-2, 4-diones, nuclear magnetic resonance, rearrangement

Abstract

3-Chloroquinoline-2,4-diones react with ethanolamine to form 3-(3-hydroxyethylamino)quinoline-2,4-diones. These compounds afford, depending on substituents in positions 1 and 3, four different products from their reaction with isothiocyanic acid: 3-(2-hydroxyethyl)-2-thioxo-3,3a-dihydro-1H-imidazo[4,5-c]quinolin-4(5H)-ones, 9b-hydroxy-3-(2-hydroxyethyl)-2-thioxo-3,3a,5,9b-tetrahydro-1H-imidazo[4,5-c]quinolin-4(2H)-ones, 3-(2-hydroxyethyl)-2-thioxo-2,3-dihydro-1H-imidazo[4,5-c]quinolin-4(5H)-ones, or 1'-methyl-7a-phenyl-5-thioxo-3,5,6,7a-tetrahydro-2H-spiro[imidazo[5,1-b]oxazole-7,3'-indolin]-2'-one.

Downloads

Published

2020-05-28

Issue

Vol. 56 No. 5 (2020)

Section

Original Papers