期刊
SYNTHESIS-STUTTGART
卷 53, 期 2, 页码 371-382出版社
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0040-1705941
关键词
2-carbamimidoylbenzoic acid; ring closure; 2-(pyrimidin-2-yl)benzoic acids; 4,6-dihydropyrimido[2,1-a]isoindole-4,6-dione; chromone ring opening; green chemistry
A new synthesis approach for 2-(pyrimidin-2-yl)benzoic acids has been developed based on the ring contraction of 2-carbamimidoylbenzoic acid with 1,3-dicarbonyl compounds. The obtained acids can undergo intramolecular condensation and further cyclization reactions to form diverse compounds with pyrrolidone or benzo[4,5]furo[3,2-d]pyrimidin moieties.
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.
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