Reaction of 3‐Hydroxyquinoline‐2,4‐diones with Inorganic Thiocyanates in the Presence of Ammonium or Alkylammonium Ions: the Unexpected Replacement of a Hydroxy Group by an Amino Group |
| |
| Authors: | Antonín Klásek Ondřej Rudolf Michal Rouchal Antonín Lyčka |
| |
| Affiliation: | 1. Department of Chemistry, Faculty of Technology, Tomas Bata University, CZ‐762 72 Zlín;2. Department of Fat, Surfactant and Cosmetics Technology, Faculty of Technology, Tomas Bata University, CZ‐762 72 Zlín;3. Research Institute for Organic Syntheses (VUOS), Rybitví 296, CZ‐533 54 Pardubice;4. University of Hradec Králové, Faculty of Science, CZ 500 03 Hradec Králové 3 |
| |
| Abstract: | 3‐Hydroxyquinoline‐2,4‐diones react with KSCN in the presence of the NH$rm{{_{4}^{+}}}$ ions to generate 2,3‐dihydro‐3‐thioxoimidazo[1,5‐c]quinazolin‐5(6H)‐ones, 2,3‐dihydro‐2‐thioxo‐1H‐imidazo[4,5‐c]quinolin‐4(5H)‐ones, and products of molecular rearrangement of the 3‐aminoquinolinedione intermediates. Starting compounds with a benzyl (Bn) group at C(3) afford 3‐aminoquinolinediones, even when only AcONH4 is used. The results of the reaction between 3‐hydroxyquinoline‐2,4‐diones and KSCN in the presence of BuNH2 show that replacing a OH group with a secondary NH2 group is also possible. |
| |
| Keywords: | Quinoline‐2,4‐diones, 3‐amino‐ Debenzylation β ‐Dicarbonyl compounds Molecular rearrangement Thioamides |
|
|
