Synthesis of a new scaffold: the 7H,8H-pyrimido[1,6-b]pyridazin-6,8-dione nucleus.
This paper describes a modified method of preparation of a number of alpha-aryl-alpha-(pyridazin-3-yl)-acetonitriles via the C-arylation reaction of the corresponding carbanionsof phenylacetonitriles using 3-chloropyridazine derivatives. KOH and DMSO were used inthe deprotonation process, which made the reaction very simple and safe to perform.Nitriles were obtained in the hydrolysis reaction to the corresponding alpha-aryl-alpha-(pyridazin-3-yl)-acetamide derivatives, which were next subjected to cyclization to afford the finalproducts. A number of new derivatives of 7H,8H-pyrimido[1,6-b]pyridazin-6,8-dione weresynthesized in the cyclocondensation reaction of respective alpha-aryl-alpha-(pyridazin-3-yl)-acetamides with diethyl carbonate in the presence of EtONa. The structure andcomposition of the new compounds were confirmed by IR, (1)H- and (13)C- NMR analysesand by elemental C, H and N analysis.
Herold
Franciszek
F
Department of Drug Technology, Faculty of Pharmacy, Medical University of Warsaw, Banacha 1 Str., 02-097 Warsaw, Poland. herold@farm.amwaw.edu.pl
Kałucka
Małgorzata
M
Król
Marek
M
Herold
Joanna
J
Kleps
Jerzy
J
Turło
Jadwiga
J
D009682:Magnetic Resonance Spectroscopy; D011724:Pyridazines / Q000138:chemical synthesis* / Q000737:chemistry
D011724:Pyridazines