2-Carbamimidoylbenzoic Acid as a New Effective and Available Precursor for the Synthesis of Substituted 2-(Pyrimidin-2-yl)benzoic Acids

Volodymyr A. Tkachuk; Vyacheslav O. Shishkanu; Tetiana M. Tkachuk; Svitlana V. Shishkina; Olga V. Hordiyenko

doi:10.1055/s-0040-1705941

Synthesis, Table of Contents

Synthesis 2021; 53(02): 371-382
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

Volodymyr A. Tkachuk

^aTaras Shevchenko National University of Kyiv, Faculty of Chemistry, 64/13 Volodymyrs’ka Str., Kyiv 01601, Ukraine Email: ov_hordiyenko@chem.knu.ua

,

Vyacheslav O. Shishkanu

^aTaras Shevchenko National University of Kyiv, Faculty of Chemistry, 64/13 Volodymyrs’ka Str., Kyiv 01601, Ukraine Email: ov_hordiyenko@chem.knu.ua

,

Tetiana M. Tkachuk

^bSMC Ecopharm Ltd, 136-B Naberezhno-Korchuvatska Str., Kyiv 03045, Ukraine

,

Svitlana V. Shishkina

^cSSI ‘Institute for Single Crystals’ of National Academy of Sciences of Ukraine, 60 Nauky Ave., Kharkiv 61072, Ukraine

,

Olga V. Hordiyenko ∗

^aTaras Shevchenko National University of Kyiv, Faculty of Chemistry, 64/13 Volodymyrs’ka Str., Kyiv 01601, Ukraine Email: ov_hordiyenko@chem.knu.ua

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Abstract

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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 chemistry

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References

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