Synthesis of Polycyclic Systems Based on Sulfolenes
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EW To the 80th anniversary of V.M. Berestovitskaya
Synthesis of Polycyclic Systems Based on Sulfolenes I. E. Efremovaa,*, L. V. Lapshinab, R. I. Baichurina, A. V. Serebryannikovac, and I. I. Savel’eva a
Herzen State Pedagogical University of Russia, St. Petersburg, 191186 Russia b Kirov Military Medical Academy, St. Petersburg, 194044 Russia с St. Petersburg State University, St. Petersburg, 199034 Russia *e-mail: [email protected] Received May 5, 2020; revised May 5, 2020; accepted May 16, 2020
Abstract—The review analyzes and summarizes methods for the synthesis of polycyclic derivatives of sulfolane (sulfolene). The reactions of polyalkylation, transformations of functional groups of the sulfolene ring, as well as the addition reaction at endo- and exocyclic multiple bonds are considered. Keywords: sulfolenes, dihydrothiophene-1,1-dioxides, polycyclic structures, alkylation, binucleophiles
DOI: 10.1134/S1070363220080010 1. INTRODUCTION 2. POLYALKYLATION OF 2,5-DIHYDROTHIOPHENE-1,1-DIOXIDE DERIVATIVES 3. REACTIONS INVOLVING SUBSTITUENTS OF THE SULFOLENE RING 4. ADDITION REACTIONS 5. CONCLUSIONS
1. INTRODUCTION Sulfolenes (dihydrothiophene-1,1-dioxides) and their derivatives are widely used in the synthesis of various cyclic compounds [1, 2], among which biologically active substances have been found, namely influenza virus neuraminidase inhibitors [3], antipsychotic substances [4], potassium channel blockers [5], photoactive substances [6], analogues of antibiotics of a hydrogenated anthraquinone series [7], as well as precursors of natural compounds [8, 9]. For the first time, data on methods for the preparation of polycycles, including sulfolane (sulfolene), have been reviewed in 1998 [10]. In the following decades, a significant number of publications devoted to this topic appeared; some of them are summarized in the review [1]. In order to systematize the synthetic approaches based on dihydrothiophene-1,1-dioxides and to identify trends in their development, herein we summarized and analyzed data on the methods for obtaining polycyclic systems containing sulfolane or sulfolene fragment since 1972. It seemed important to assess the synthetic potential
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of sulfolene and its derivatives in the construction of polycyclic structures due to CH-acidity of methylene groups of dihydrothiophene-1,1-dioxide (polyalkylation reactions), the presence of endo- and exocyclic multiple bonds, as well as reactive functional groups (addition reactions, substitution reactions, etc.). The review does not consider the diene synthesis reactions leading to the loss of the sulfolane ring [10–12], as well as the methods in which the dihydrothiophene-1,1-dioxide system is formed at the final stages and does not participate in the formation of polycycles [10, 13–16]. 2. POLYALKYLATION OF 2,5-DIHYDROTHIOPHENE-1,1-DIOXIDE DERIVATIVES Polyalkylation reactions of 2,5-dihydrothiophene1,1-dioxide derivatives, first proposed by Taiwanese chemists, turned out to be very promising for the design of polycycles combinin
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