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New Insights into Furans Transformations

A special issue of Molecules (ISSN 1420-3049). This special issue belongs to the section "Organic Chemistry".

Deadline for manuscript submissions: closed (15 September 2021) | Viewed by 5875

Special Issue Editors

N.D. Zelinsky Institute of Organic Chemistry Russian Academy of Sciences, Leninsky pr. 47, Moscow, Russia
Interests: chemistry of donor–acceptor cyclopropanes; transformations of furans to other heterocycles
Department of Chemistry, Perm State University, Bukireva 15, Perm, Russia
Interests: chemistry of heterocyclic compounds; transformations of furans; dearomatization; catalysis; new synthetic methods; the synthesis of natural and biologically active compounds

Special Issue Information

Dear Colleagues,

We are happy to be Guest Editors of the Special Issue of Molecules, devoted to “New Insights into Furans Transformations”. The chemistry of furan, on the one hand, has a long history, but on the other hand, it has received a new life after developments of methods for the large-scale preparation of furan derivatives during biomass processing. These technological advances stimulated studies of diverse modifications of simple furans to polysubstituted ones and investigations of furans transformations to various acyclic, alicyclic, and, especially, heterocyclic molecules. For example, furans acylation or alkylation followed by hydrogenation can be used for the preparation of diesel fuel or gasoline additives. Both intermolecular and intramolecular versions of the Diels-Alder reaction followed by post-modifications of the formed [4+2]-cycloadducts are used for the synthesis of carbo- and heterocycles, including total synthesis of natural products. Another important area of furans transformations is a diversity of acid-induced rearrangement, such as the Piancatelli rearrangement, Butin reaction, and other processes. In recent years, the related Lewis acid-induced and π-acid-catalyzed processes have attracted increasing attention. In addition to the Achmatowicz reaction, whose 50th anniversary is in 2021, many other oxidative transformations of furans are under development. We are inviting reviews and original reports devoted to various aspects of furans transformations, both those mentioned and others not described here, and hope that this Special Issue will be of great interest to the organic chemistry community.

Prof. Dr. Igor V. Trushkov
Dr. Maxim G. Uchuskin
Guest Editors

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Keywords

  • Furans
  • Cycloaddition
  • Dearomatization
  • Rearrangement
  • Oxidative transformations
  • Organic synthesis
  • Synthetic methods
  • Multicomponent reactions
  • Natural and bioactive compounds
  • Domino reactions

Published Papers (2 papers)

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Research

12 pages, 1065 KiB  
Communication
Transformation of 3-(Furan-2-yl)-1,3-di(het)arylpropan-1-ones to Prop-2-en-1-ones via Oxidative Furan Dearomatization/2-Ene-1,4,7-triones Cyclization
by Roman O. Shcherbakov, Diana A. Eshmemet’eva, Anton A. Merkushev, Igor V. Trushkov and Maxim G. Uchuskin
Molecules 2021, 26(9), 2637; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules26092637 - 30 Apr 2021
Cited by 2 | Viewed by 2459
Abstract
The approach to 3-(furan-2-yl)-1,3-di(het)arylprop-2-en-1-ones based on the oxidative dearomatization of 3-(furan-2-yl)-1,3-di(het)arylpropan-1-ones followed by an unusual cyclization of the formed di(het)aryl-substituted 2-ene-1,4,7-triones has been developed. The cyclization step is related to the Paal–Knorr synthesis, but the furan ring formation is accompanied in this case [...] Read more.
The approach to 3-(furan-2-yl)-1,3-di(het)arylprop-2-en-1-ones based on the oxidative dearomatization of 3-(furan-2-yl)-1,3-di(het)arylpropan-1-ones followed by an unusual cyclization of the formed di(het)aryl-substituted 2-ene-1,4,7-triones has been developed. The cyclization step is related to the Paal–Knorr synthesis, but the furan ring formation is accompanied in this case by a formal shift of the double bond through the formation of a fully conjugated 4,7-hydroxy-2,4,6-trien-1-one system or its surrogate. Full article
(This article belongs to the Special Issue New Insights into Furans Transformations)
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15 pages, 2818 KiB  
Article
Application of New Efficient Hoveyda–Grubbs Catalysts Comprising an N→Ru Coordinate Bond in a Six-Membered Ring for the Synthesis of Natural Product-Like Cyclopenta[b]furo[2,3-c]pyrroles
by Alexandra S. Antonova, Marina A. Vinokurova, Pavel A. Kumandin, Natalia L. Merkulova, Anna A. Sinelshchikova, Mikhail S. Grigoriev, Roman A. Novikov, Vladimir V. Kouznetsov, Kirill B. Polyanskii and Fedor I. Zubkov
Molecules 2020, 25(22), 5379; https://0-doi-org.brum.beds.ac.uk/10.3390/molecules25225379 - 17 Nov 2020
Cited by 7 | Viewed by 2901
Abstract
The ring rearrangement metathesis (RRM) of a trans-cis diastereomer mixture of methyl 3-allyl-3a,6-epoxyisoindole-7-carboxylates derived from cheap, accessible and renewable furan-based precursors in the presence of a new class of Hoveyda–Grubbs-type catalysts, comprising an N→Ru coordinate bond in a six-membered ring, results [...] Read more.
The ring rearrangement metathesis (RRM) of a trans-cis diastereomer mixture of methyl 3-allyl-3a,6-epoxyisoindole-7-carboxylates derived from cheap, accessible and renewable furan-based precursors in the presence of a new class of Hoveyda–Grubbs-type catalysts, comprising an N→Ru coordinate bond in a six-membered ring, results in the difficult-to-obtain natural product-like cyclopenta[b]furo[2,3-c]pyrroles. In this process, only one diastereomer with a trans-arrangement of the 3-allyl fragment relative to the 3a,6-epoxy bridge enters into the rearrangement, while the cis-isomers polymerize almost completely under the same conditions. The tested catalysts are active in the temperature range from 60 to 120 °C at a concentration of 0.5 mol % and provide better yields of the target tricycles compared to the most popular commercially available second-generation Hoveyda–Grubbs catalyst. The diastereoselectivity of the intramolecular Diels–Alder reaction furan (IMDAF) reaction between starting 1-(furan-2-yl)but-3-en-1-amines and maleic anhydride, leading to 3a,6-epoxyisoindole-7-carboxylates, was studied as well. Full article
(This article belongs to the Special Issue New Insights into Furans Transformations)
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