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2-Carbamimidoylbenzoic Acid as a New Effective and Available Precursor for the Synthesis of Substituted 2-(Pyrimidin-2-yl)benzoic Acids
Synthesis ( IF 2.2 ) Pub Date : 2020-11-16 , DOI: 10.1055/s-0040-1705941
Olga V. Hordiyenko 1 , Volodymyr A. Tkachuk 1 , Vyacheslav O. Shishkanu 1 , Tetiana M. Tkachuk 2 , Svitlana V. Shishkina 3
Affiliation  

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.



中文翻译:

2-氨基甲酰氨基苯甲酸作为合成取代的2-(嘧啶-2-基)苯甲酸的新型有效和可用的前体

基于2-氨基甲酰氨基苯甲酸[(2-ami基苯甲酸)]与1,3-二羰基化合物及其合成等效物的环收缩,合成2-(嘧啶-2-基)苯甲酸的新方法已经得到。发达。所获得的酸与1,3-二亲电子分子的分子内缩合继续形成4,6-二氢嘧啶基[2,1 - a ]异吲哚-4,6-二酮体系,其吡咯烷酮环在环戊烷下容易打开。弱亲核试剂的作用。2-ami基苯甲酸与在3-位具有芳氧基的色酮的反应不会在嘧啶环形成的步骤中停止,并且会进一步自发环化为2-(苯并[4,5]呋喃[3,2- d ]嘧啶-2-基)苯甲酸。

更新日期:2020-11-17
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