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Synthesis 2021; 53(02): 371-382
DOI: 10.1055/s-0040-1705941
DOI: 10.1055/s-0040-1705941
paper
2-Carbamimidoylbenzoic Acid as a New Effective and Available Precursor for the Synthesis of Substituted 2-(Pyrimidin-2-yl)benzoic Acids
Abstract
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.
Key words
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 chemistrySupporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1705941.
- Supporting Information
Publication History
Received: 25 June 2020
Accepted after revision: 16 September 2020
Article published online:
16 November 2020
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