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Synthesis of a New Scaffold: the 7H,8H-Pyrimido[1,6-b]pyridazin-6,8-dione Nucleus
Department of Drug Technology, Faculty of Pharmacy, Medical University of Warsaw, Banacha 1 Str., 02-097 Warsaw, Poland
Department of Drug Chemistry, Faculty of Pharmacy, Medical University of Warsaw, Banacha 1 Str., 02-097 Warsaw, Poland
* Author to whom correspondence should be addressed.
Received: 6 December 2007; in revised form: 21 December 2007 / Accepted: 21 December 2007 / Published: 30 December 2007
Abstract: This paper describes a modified method of preparation of a number of α-aryl-α-(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 α-aryl-α-(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 α-aryl-α-(pyridazin-3-yl)-acetamides with diethyl carbonate in the presence of EtONa. The structure andcomposition of the new compounds were confirmed by IR, 1H- and 13C- NMR analysesand by elemental C, H and N analysis.
Keywords: α-Aryl-α-(pyridazin-3-yl)-acetonitrile; C-arylation; α-aryl-α-(pyridazin-3-yl)- acetamides; 7H; 8H-pyrimido[1; 6-b]pyridazin-6; 8-diones
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MDPI and ACS Style
Herold, F.; Kałucka, M.; Król, M.; Herold, J.; Kleps, J.; Turło, J. Synthesis of a New Scaffold: the 7H,8H-Pyrimido[1,6-b]pyridazin-6,8-dione Nucleus. Molecules 2007, 12, 2643-2657.
Herold F, Kałucka M, Król M, Herold J, Kleps J, Turło J. Synthesis of a New Scaffold: the 7H,8H-Pyrimido[1,6-b]pyridazin-6,8-dione Nucleus. Molecules. 2007; 12(12):2643-2657.
Herold, Franciszek; Kałucka, Małgorzata; Król, Marek; Herold, Joanna; Kleps, Jerzy; Turło, Jadwiga. 2007. "Synthesis of a New Scaffold: the 7H,8H-Pyrimido[1,6-b]pyridazin-6,8-dione Nucleus." Molecules 12, no. 12: 2643-2657.