1,3-Dimethylbarbituric acid

1,3-Dimethylbarbituric acid.svg 175px 1,3-Dimethyl-2,4,6(1H,3H,5H)-pyrimidinetrione 1,3-Dimethylbarbituric acid N,N′-Dimethylbarbituric acid 1,3-Dimethyl-pyrimidine-2,4,6-trione 6-Hydroxy-1,3-dimethyluracil 769-42-6 63056 212-211-7 69860 8ZWY29H946 O=C1N(C(=O)CC(=O)N1C)C 1S/C6H8N2O3/c1-7-4(9)3-5(10)8(2)6(7)11/h3H2,1-2H3 VVSASNKOFCZVES-UHFFFAOYSA-N 6 8 2 3 4.70 05 07 Danger 302 318 264 264+265 270 280 301+317 305+354+338 317 330 501 1,3-Dimethylbarbituric acid (N,N′-dimethylbarbituric acid) is an analog of barbituric acid having a methyl group on each of the two nitrogen atoms. It is an intermediate in chemical synthesis, being easily formed by a condensation reaction of 1,3-dimethylurea and malonic acid. A notable application of that reaction and subsequent steps is Emil Fischer's first total synthesis of caffeine. Faudone Giuseppe Arifi Silvia Merk Daniel The Medicinal Chemistry of Caffeine Journal of Medicinal Chemistry 2021 64 11 7156–7178 10.1021/acs.jmedchem.1c00261 34019396 The methylene group (–CH2–) is fairly acidic, being alpha to two carbonyl groups, and undergoes Knoevenagel condensation reactions with aldehydes Asiri A.M. Al-Amoudi M.S. Synthesis, characterisation and thermal stability of 5-ferrocenylidene-(1,3-dimethylbarbituric acid) and 5-ferrocenylidene-(1,3-diethylthiobarbituric acid) Pigment & Resin Technology 2006 35 5 270–277 10.1108/03699420610692878 and ketonesPałasz Aleksandra Pałasz, Tadeusz Knoevenagel condensation of cyclic ketones with benzoylacetonitrile and N,N′-dimethylbarbituric acid. Application of sterically hindered condensation products in the synthesis of spiro and dispiropyrans by hetero-Diels–Alder reactions Tetrahedron 18 February 2011 67 7 1422–1431 10.1016/j.tet.2010.12.053 and also acylation reactions. Liu Yue Li Peng-Xiao Mu Wen-Wen Sun Ya-Lei Liu Ren-Min Yang Jie Liu Guo-Yun Design, Synthesis, and Anticancer Activity of Cinnamoylated Barbituric Acid Derivatives Chemistry & Biodiversity 2022 19 2 e202100809 10.1002/cbdv.202100809 34931450 The 1,3-dimethylbarbituric acid substructure motif has found application in several compounds that have cytotoxic properties against cancer cells. References Category:Barbiturates Category:Methyl compounds