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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
a   Taras 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
a   Taras 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 
b   SMC Ecopharm Ltd, 136-B Naberezhno-Korchuvatska Str., Kyiv 03045, Ukraine
,
Svitlana V. Shishkina
c   SSI ‘Institute for Single Crystals’ of National Academy of Sciences of Ukraine, 60 Nauky Ave., Kharkiv 61072, Ukraine
,
Olga V. Hordiyenko  ∗
a   Taras 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

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

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/s-0040-1705941.
  • Supporting Information


Publikationsverlauf

Eingereicht: 25. Juni 2020

Angenommen nach Revision: 16. September 2020

Artikel online veröffentlicht:
16. November 2020

© 2020. Thieme. All rights reserved

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