Synthesis of 7-aryl-6,7-dihydrotetrazolo[1,5-a]pyrimidin-5(4H)-ones

Authors

  • N. V. Svitlichna DU "Institute of Problems of Endocrine Pathology named after. V.Ya. Danilevsky National Academy of Sciences of Ukraine», Ukraine
  • V. V. Borodina DU "Institute of Problems of Endocrine Pathology named after. V.Ya. Danilevsky National Academy of Sciences of Ukraine», Ukraine
  • V. V. Lipson V.N.Karazin Kharkiv National University, DNU "NTK" Institute of Single Crystals "of the National Academy of Sciences of Ukraine, Ukraine
  • V. I. Musatov DNU "NTK" Institute of Single Crystals "of the National Academy of Sciences of Ukraine, Ukraine

DOI:

https://doi.org/10.24959/ophcj.14.785

Keywords:

1H-tetrazol-5-amine, 1, 3-carbonyl bielectrophiles, methylcinnamates, arylmethylidenmalonic acids

Abstract

Arylmethyliden derivatives of 2,2-dimethyl-1,3-dioxane-4,6-dione; Meldrum`s acid; 6,7-dihydro-7-aryltetrazolo [1,5-a]pyrimidin-5(4H)-ones; synthesis; pharmacological activity
Cyclocondensations of 1H-tetrazol-5-amine with methylcinnamates, arylmethyliden malonic acids and arylmethyliden derivatives of 2,2-dimethyl-1,3-dioxane-4,6-dione (Meldrum`s acid) proceed regioselectively and lead to formation of 7-aryl-6,7-dyhidrotetrazolo[1,5-a]pyrimidin-5(4H)-ones. The direction of cyclization corresponds to the interaction of the carbon atom in β-position of the unsaturated carbonyl compounds with the endocyclic nitrogen atom and the carbonyl group with amino group in the aminoazole molecule. Compounds of the isomeric structure in any of the experiments have been not identified. The structures and composition of the newly synthesized tetrazolo[1,5-a]pyrimidin-5(4H)-ones have been confirmed by elemental analysis, infrared spectroscopy (IR), nuclear magnetic resonance on protones (1H NMR) and mass spectra data. Virtual screening of 7-aryl-6,7-dihydrotetrazolo[1,5-a]pyrimidin-5(4H)-ones carried out using the PASS programme for 780 types of the pharmacological action has demonstrated that it is expedient to test these compounds by their analgesic and anti-inflammatory activity, as well as as potential agents for the treatment of heart failure.

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Published

2014-03-06

How to Cite

(1)
Svitlichna, N. V.; Borodina, V. V.; Lipson, V. V.; Musatov, V. I. Synthesis of 7-Aryl-6,7-dihydrotetrazolo[1,5-a]pyrimidin-5(4H)-Ones. J. Org. Pharm. Chem. 2014, 12, 47-50.

Issue

Vol. 12 No. 1(45) (2014)

Section

Original Researches

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