86454-11-7Relevant academic research and scientific papers
2-Carbamimidoylbenzoic Acid as a New Effective and Available Precursor for the Synthesis of Substituted 2-(Pyrimidin-2-yl)benzoic Acids
Tkachuk, Volodymyr A.,Shishkanu, Vyacheslav O.,Tkachuk, Tetiana M.,Shishkina, Svitlana V.,Hordiyenko, Olga V.
, p. 371 - 382 (2020/12/01)
A new approach to the synthesis of 2-(pyrimidin-2-yl)benzoic acids based on the ring contraction of the 2-carbamimidoylbenzoic acid [(2-amidinobenzoic) acid] with 1,3-dicarbonyl compounds and their synthetic equivalents has been developed. The intramolecular condensation of the obtained acids with 1,3-dielectrophiles proceeds with the formation of the 4,6-dihydropyrimido[2,1- a ]isoindole-4,6-dione system, the pyrrolidone ring of which is easily opened under the action of weak nucleophiles. The reaction of 2-amidinobenzoic acid with chromones, which have an aryloxy group at 3-position does not stop at the step of pyrimidine ring formation and undergoes further spontaneous cyclization into 2-(benzo[4,5]furo[3,2- d ]pyrimidin-2-yl)benzoic acids.
Reaction of β-Aminocrotonamide with Dibasic Acid Derivatives
Sato, Masayuki,Ogasawara, Hiromichi,Kato, Tetsuzo
, p. 87 - 91 (2007/10/02)
Reaction of β-aminocrotonamide (1) with succinic anhydride gave β-succinamidocrotonamide (3a), which was treated with base to cyclize to 3,4-dihydro-6-methyl-4-oxo-2-pyrimidinepropanoic acid (4a).Similarly, pyrimidinepentanoic acid derivative 4b was prepared from compound 1 and glutaric anhydride.Reaction of compound 1 with dimethyl succinate in the presence of sodium methoxide gave the pyrimidine derivative 4a.Similar reaction of compound 1 with glutarate, adipate, and phthalate gave the corresponding pyrimidines 4b, 4c and 4d, while reaction of compound 1 with malon ate gave 2-hydroxypyridine derivative 11 and dimethylpyrimidinone 4e.Reaction of dimethyl fumarate with compound 1 in the presence of methoxide gave a poor yield of pyrrolopyridine derivative 13.
