Synthesis of 4,6-Disubstituted 2-Thioxo-1,2-dihydropyridine-3-carbonitriles by the Reaction of Acetylenic Ketones with Cyanothioacetamide

D. S. Buryi; V. V. Dotsenko; A. S. Levashov; D. Yu. Lukina; V. D. Strelkov; N. A. Aksenov; I. V. Aksenova; E. E. Netreba

doi:10.1134/S1070363219050050

Synthesis of 4,6-Disubstituted 2-Thioxo-1,2-dihydropyridine-3-carbonitriles by the Reaction of Acetylenic Ketones with Cyanothioacetamide

Authors: Buryi D.S.¹, Dotsenko V.V.¹^,2, Levashov A.S.¹, Lukina D.Y.¹, Strelkov V.D.¹, Aksenov N.A.¹, Aksenova I.V.², Netreba E.E.³
Affiliations:
1. Kuban State University
2. North-Caucasus Federal University
3. V.I. Vernadsky Taurida Academy
Issue: Vol 89, No 5 (2019)
Pages: 886-895
Section: Article
URL: https://journals.rcsi.science/1070-3632/article/view/222894
DOI: https://doi.org/10.1134/S1070363219050050
ID: 222894

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Abstract

The reaction of acetylenic ketones with cyanothioacetamide in the presence of morpholine yields 4,6-disubstituted 2-thioxo-1,2-dihydropyridine-3-carbonitriles. Structure of the obtained compounds was proved using 2D NMR spectroscopy, as well as transformations into 3-aminothieno[2,3-b]pyridine-2-carboxamide derivatives.

Keywords

acetylenic ketones, cyanothioacetamide, Bohlmann-Rahtz reaction, Thorpe-Ziegler reaction, thieno-[2,3-b]pyridines