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2017, № 69

UDC: 547.83
GSNTI: 31.21.27

Research of reactions of electrophillic substitution of ethyl 3-(1-pyrrolyl) thieno [2,3-b] pyridine -2- carboxylate

This article relates to organic Chemistry, namely to chemistry of heterocyclic compounds. 3-(1-pyrrolyl) thieno [2,3-b]pyridines, being chemically available substances, are of interest as convenient objects for functualization and search of physiologically active substances with predictable properties among them. Based on ethyl 3-(1-pyrrolyl)thieno[2,3-b] pyridincarboxylate the reactions of electrophillic (SE) substitution were studied: halogenation and formylation on Wilsmeier, nitration, acylation. It was determined that iodination (potassium iodine, acetic acid, ethyl spirit, peroxide of hydrogen) and bromination (bromine, acetic acid, heating) does not lead to the obtaining the sougnt-for products. Similar results were obtained in attempt to introduce the formyl groups in the pyrrole ring (dimethylformamide / phosphorus trichloride). Under nitration of ethyl 3-(1-pyrrolyl)thieno[2,3-b] pyridine-carboxylate in harsh conditions using the acetyl nitrate in output of 82%, a mixture of mono nitration products was obtained for the α- and β-positions of the pyrrole ring. Because of practically similar polarity of molecules and consequently the closer values of coefficients of movement in different eluents,we failed in splitting the products, which are structural isomers. The structure of obtained mono-nitro-derivatives was determined by the method of 1H- NMR of spectroscopy. Individual products of acetylation of ethyl 3-(1-pyrrolyl) thieno [2,3-b] pyridine carboxylate were synthesized using the acetic anhydride with presence of chloric acid as a catalyst. 2- and 3-acetyl-derivatives were divided by preparative columnar chromatography and obtained with output of 33 and 46%, respectively. Compounds were characterized on the basis of elementary analysis data and 1H- NMR of spectra.
Keywords: Heterocyclic compounds, organic synthesis, ethyl 3-(1-pyrrolyl) thieno [2,3-b] pyridine carboxylate, reactions of electrophilic substitution, 1H- NMR spectrometry
DOI: 10.21515/1999-1703-69-164-170

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Authors:

1. Osipova Anzhelika Avtandilovna, PhD in Chemistry, instructor of Krasnodar Technical School, The Krasnodar technical school.
2. Kaigorodova Elena Alekseevna, Drс Chemical, professor; Department of non-organic and analytical chemistry, Federal State Budgetary Educational Institution of Higher Education “I.T. Trubilin Kuban State Agrarian University”.
3. Kostenko Ekaterina Sergeevna, PhD in Chemistry, associate professor; Department of non-organic and analytical chemistry, Federal State Budgetary Educational Institution of Higher Education “I.T. Trubilin Kuban State Agrarian University”.
4. Kosyanok Nina Yevgenievna, PhD in Pharmaceutics, associate professor; Department of non-organic and analytical chemistry, Federal State Budgetary Educational Institution of Higher Education “I.T. Trubilin Kuban State Agrarian University”.