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- Title
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
Klásek, Antonín; Rouchal, Michal; Rudolf, Ondřej; Lyčka, Antonín
- 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(6 H)-ones, 2,3-dihydro-2-thioxo-1 H-imidazo[4,5- c]quinolin-4(5 H)-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.
- Subjects
HYDROXYQUINOLINE; REARRANGEMENTS (Chemistry); THIOCYANATES; AMMONIUM ions; AMINO group; ISOCYANATES; CARBOCATIONS
- Publication
Helvetica Chimica Acta, 2015, Vol 98, Issue 3, p318
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.201400189