Recent advances in the chemistry of thieno[2,3- b ]pyridines 1. Methods of synthesis of thieno[2,3- b ]pyridines
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Recent advances in the chemistry of thieno[2,3-b]pyridines 1. Methods of synthesis of thieno[2,3-b]pyridines* V. V. Dotsenko,a,b,c D. S. Buryi,a D. Yu. Lukina,a and S. G. Krivokolyskoc,d аKuban
State University, 149 ul. Stavropolskaya, 350040 Krasnodar, Russian Federation. E-mail: [email protected] bNorth Caucasus Federal University, 1A ul. Pushkina, 355009 Stavropol', Russian Federation cVladimir Dal´ Lugansk National University, Scientific Research Laboratory "Khimeks", Korp. 7, 20a kv. Molodezhny, 91034 Lugansk dSt. Luka Lugansk State Medical University, 1g kv. 50-Letiya Oborony Luganska, 91045 Lugansk The recent data (2007—2018) on the synthesis of thieno[2,3-b]pyridines are summarized and systematized. Keywords: thieno[2,3-b]pyridines, Thorpe—Ziegler reaction, Gewald´s 2-aminothiophenes, nicotinonitriles, cyanothioacetamide, Friedländer reaction, Gould—Jacobs reaction.
1. Introduction The chemistry of thieno[2,3-b]pyridine derivatives has been developing rapidly since the first works appeared in the middle of the 20th century and has repeatedly become the subject of detailed consideration in monographs, reviews, and theses.1—18 Interest in thienopyridines is mainly caused by the wide range of their practically important properties: biologically active compounds, dyes, agrochemicals, etc. have been found among this class of compounds. The last work, which summarized and systematized data on the chemistry of thieno[2,3-b]pyridines in general, was published in 2007.8 Since then, significant progress has been made in this area of heterocyclic chemistry, which is reflected in a number of new publications concerning synthetic methods, modification, and especially biological activity of thieno[2,3-b]pyridine derivatives. In the Scopus database for the key term "thieno[2,3-b]pyridine" in the title, abstract, and keywords for the period from 2007 to 2019 inclusive (as of 01.04.2019), more than 300 articles and about 1000 patents were found (Fig. 1). The tremendous interest in thieno[2,3-b]pyridines reflected in a large number of publications, prompted us to summarize and systematize the data on the chemistry of these compounds for the period from the publication of the last review to the beginning of 2019. The material * Based on the materials of the V All-Russian Conference with International Participation on Organic Chemistry (September 10—14, 2018, Vladikavkaz, Russia).
of the present review is systematized according to the type of construction of thienopyridine systems. Due to the large amount of information, the review focuses on the most significant, in the authors´ opinion, works; patents and routine works containing no fundamentally new data have limited citation. The issues of functionalization of substituents, biological activity of thieno[2,3-b]pyridines, and construction of polycyclic assemblies with a condensed thienopyridine fragment will be considered in subsequent reviews. 2. Construction of thienopyridine system through the annulation of the thiophene ring Among many options for synthesizing thi
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