Donor-Acceptor Cyclopropanes as Polyfunctional Building Blocks in Organic Chemistry

Palestrante:  Prof. Dr. Igor Trushkov (Zelinsky Institute of Organic Chemistry – Russian Academy of Sciences)

Abstract:  Presentation will be devoted to results of investigations of Trushkov’s group in the chemistry of donor-acceptor cyclopropanes and will include the following points.
A selection of donor-acceptor cyclopropanes as substrates for study. Conversion of donor-acceptor cyclopropanes to other carbocycles: (3+4)-Cycloadditions of donor-acceptor cyclopropanes – first study and further development; (3+4)-Annulations of donor-acceptor cyclopropanes. Cycloadditions vs. annulations. Competition of (3+2)-annulations and –cycloadditions in reactions with alkenes; (3+2)-Annulations of donor-acceptor cyclopropanes with alkenes. Two ways of cyclization. Conversion of donor-acceptor cyclopropanes to heterocycles: (3+n)-Cycloadditions with compounds containing X=Y or XY bonds. Intermolecular three-membered ring opening with N-containing nucleophiles followed by secondary cyclizations/cycloadditions/domino processes (azide-, cyanide-, thiocyanate-ion, amines, etc.). Intramolecular three-membered ring opening. Revision of Baldwin rules for cyclopropanes. Multiple transformations of donor-acceptor cyclopropanes in the absence of other educts. Isomerizations to alkenes. Vinylcyclopropane–cyclopentene isomerization and related processes; <Other rearrangements; short comment on literature data>; Cyclodimerizations of donor-acceptor cyclopropanes; Cross-dimerizations of two different three-membered rings.

Igor V. Trushkov was born on November 5, 1964 in Serov-city, Sverdlovsk region, USSR. In 1987 he received his Ph.D. at the Moscow State University, Department of Chemistry. In 2015, he received D.Sc. degree at the same university (thesis: Furans in the Synthesis of Azaheterocycles).Since 1987 to 2016 I.V. Trushkoiv occupied various positions (including associate professor position) at the same university. Since 2016 to 2018 he was a full professor at People’s Friendship University of Russia (RUDN University). Since 2019 he is a head of the laboratory of the Directed Functionalization of Organic Molecular Systems (№ 33) at N.D. Zelinsky Institute of Organic Chemistry Russian Academy of Sciences; leading researcher, then chief researcher. Since 2010 to 2025 he also headed the Laboratory of Chemical Synthesis at the Dmitry Rogachev National Research Center of Pediatric Hematology, Oncology and Immunology.
His research interests are now related to:1) the development of new reactions of donor-acceptor cyclopropanes and the applications of the disclosed processes to the synthesis of diverse bioactive compounds, including approved drugs, as well other compounds valuable for industry; 2) the development of new transformations based on the usage of sulfur ylides as well as the corresponding sulfonium and sulfoxonium salts: predominantly – diverse versions of interrupted and extended Corey-Chaykovsky reactions; 3) the development of new transformations of furans into other heterocyclic compounds; 4) the development of a new concept on the use of protic ionic liquids as “triple-in-one” systems, namely, regenerable reaction medium, acid catalyst, source of reagents in various reactions. I. V. Trushkov is author and co-author of more than 130 papers, 22 patents, 88 teaching aids, monograph “Fullerenes” (in Russian, Moscow 2005), chapters in monographs “Fluorine in Heterocyclic Chemistry” (ed. by V. Nenajdenko, Springer, 2014) and “Donor–Acceptor Cyclopropanes in Organic Synthesis” (eds.: P. Banerjee, A. T. Biju, Wiley-VCH, 2024). In addition, I.V. Trushkov takes an active part in training new scientific personnel and encouraging schoolchildren to study chemictsry. Since 2004 he is a member of scientific committee of All-Russian chemistry Olympiad for school students. Since 2005 to 2017 and since 2024 to date he is also a member of science committee of Mendeleev Chemistry Olympiad for school students. In 2007, 2013, 2015 he was a member of science committee of International Chemistry Olympiad.

Prof. Responsável: Rodrigo Antonio Cormanich