Products of interaction of substituted 5-aminopyrazoles with α -haloketones as potential pharmaceutical agents
Journal Title: ScienceRise: Pharmaceutical Science - Year 2017, Vol 0, Issue 5
Abstract
<p><strong>Aim. </strong>Optimization of reaction of substituted 5-aminopyrazoles with a-haloketones to form annealed 2,6,7-trisubstituted 1H-imidazo[1,2-b]pyrazoles.</p><p><strong>Materials and methods of research. </strong>The methods of organic synthesis, instrumental methods of organic compound analysis were used.</p><p><strong>Results.</strong><strong> </strong>A scheme for the synthesis of 2,6,7-trisubstituted 1H-imidazo[1,2-b]pyrazoles by the interaction of 5-amino-4-arylsulfonyl-3-methylthiopyrazoles <strong>1a-b</strong> with chloroacetone, phenacyl bromide and 2-chlorocyclohexanone was developed. In contrast to the previously described interaction of substituted 5-aminopyrazoles with chloro (N-aryl) acetamides proceeding exclusively with the release of N<sup>1</sup>-alkylation products, in this reaction a mixture of N<sup>1</sup>- and N<sup>2</sup>-isomeric alkylation products is formed. The ratio of isomers depends on the nature of the reagents and, according to the 1H NMR-spectroscopy, is about 60:40 %.The developed technique allows with one of the synthetic procedure to carry out N<sup>1</sup>-alkylation of 5-aminopyrazoles <strong>1a-b</strong> and the cyclization of products <strong>2</strong> in imidazo[1,2-b]pyrazoles <strong>4a-c</strong> without isolating the N<sup>2</sup>-alkylation product. The purity of the obtained compounds is proved chromatographically, the structure is confirmed by the data of 1H NMR-spectroscopy.</p><p><strong>Conclusions.</strong> Optimized reaction of substituted 5-aminopyrazoles with a-haloketones to form annealed 2,6,7-trisubstituted 1H-imidazo[1,2-b]pyrazoles for targeted synthesis of the novel agents for the pharmaceutical practice</p>
Authors and Affiliations
Pavlo Tkachenko, Olena Tkachenko, Krystyna Netosova, Oleksandr Borisov, Iryna Zhuravel
Keywords
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- EP ID EP647887
- DOI 10.15587/2519-4852.2017.113493
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