Molecules from Multicomponent Reactions

A special issue of Molbank (ISSN 1422-8599). This special issue belongs to the section "Organic Synthesis and Biosynthesis".

Deadline for manuscript submissions: closed (30 June 2019) | Viewed by 7644

Special Issue Editor


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Guest Editor
Division of Organic Pharmaceutical Chemistry, Department of Medicinal Chemistry, BMC, Box 574, Uppsala University, S-751 23 Uppsala, Sweden
Interests: heterocyclic chemistry; multicomponent reactions; catalysis; medicinal chemistry; synthetic methodology

Special Issue Information

Dear Colleagues,

This Special Issue is devoted to the fascinating topic of multicomponent reactions (MCRs). These reactions are a group of powerful and highly convergent chemical transformations capable of generating enormous structural diversity by reacting three or more starting materials simultaneously. These reactions utilize subtle differences in reactivity between various functional groups to allow a predictable series of reactions to occur in the same vessel, leading to the formation of the desired product. Furthermore, the product incorporates the vast majority of atoms from all starting materials in its framework, making MCRs inherently efficient and sustainable processes. There has been a tremendous amount of interest in MCRs over the last few decades and, as the demands for new and sustainable materials and medicines continue to increase, the topic will undoubtedly remain a focal point for synthetic chemists around the world.

Prof. Dr. Luke R. Odell
Guest Editor

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Keywords

  • multicomponent reaction
  • chemical diversity
  • green chemistry
  • one-pot reactions

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Published Papers (3 papers)

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Research

8 pages, 478 KiB  
Communication
(E)-3-(2,5-Dimethoxyphenyl)-1-{[4-(2,5-dimethoxy-phenyl)-6-((E)-2,5-dimethoxystyryl)-2-thioxo-1,2,3,4-tetrahydropyrimidin-5-yl]}prop-2-en-1-one and (E)-3-(2,5-Dimethoxyphenyl)-1-{[4-(2,5-dimethoxyphenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydropyrimidin-5-yl]}prop-2-en-1-one
by Hery Suwito, Noorma Kurnyawaty, Ellyca Susetyo, Yuzkiya Azizah, Kautsar Ul Haq, Alfinda Novi Kristanti and Indriani Indriani
Molbank 2019, 2019(2), M1063; https://doi.org/10.3390/M1063 - 4 Jun 2019
Viewed by 2244
Abstract
Dihydropyrimidine derivatives possess great potential to be used as a precursor for the synthesis of wide diverse dihydropyrimidine-like derivatives. In this research, the title compounds were synthesized through the reaction between 5-acetyl-4-(2,5-dimethoxyphenyl)-6-methyl-3,4-dihydropyrimidin-2(1H)-thione and 2,5-dimethoxybenzladehyde under aldol condensation condition. The title compound, [...] Read more.
Dihydropyrimidine derivatives possess great potential to be used as a precursor for the synthesis of wide diverse dihydropyrimidine-like derivatives. In this research, the title compounds were synthesized through the reaction between 5-acetyl-4-(2,5-dimethoxyphenyl)-6-methyl-3,4-dihydropyrimidin-2(1H)-thione and 2,5-dimethoxybenzladehyde under aldol condensation condition. The title compound, (E)-3-(2,5-dimethoxyphenyl)-1-{[(4-(2,5-dimethoxyphenyl)-6-((E)-2,5-dimethoxystyryl)-2-thioxo-1,2,3,4-tetrahydropyrimidin-5-yl)]}prop-2-en-1-one (yield 15%), was obtained as major product, whereas (E)-3-(2,5-dimethoxyphenyl)-1-{[(4-(2,5-dimethoxyphenyl)-6-methyl-2-thioxo-1,2,3,4-tetrahydro pyrimidin-5-yl)]}prop-2-en-1-one (yield 8%) as side product through vinylogous aldol condensation. Full article
(This article belongs to the Special Issue Molecules from Multicomponent Reactions)
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5 pages, 899 KiB  
Short Note
5-[(Z)-5-Chloro-2-oxoindolin-3-ylidene]-3-{(E)-[(4-hydroxyphenyl)imino]methyl}-2-thioxothiazolidin-4-one
by Abdelmounaim Safer, Khadidja Khaldoun and Salima Saidi-Besbes
Molbank 2019, 2019(2), M1059; https://doi.org/10.3390/M1059 - 6 May 2019
Viewed by 1853
Abstract
N-aminorhodanine as well as isatin are highly solicited motifs known for their wide potential for biological activity. The objective of this work was to synthesize hybrid molecules as kinase inhibitors from these two motifs. In order to study the reactivity of the [...] Read more.
N-aminorhodanine as well as isatin are highly solicited motifs known for their wide potential for biological activity. The objective of this work was to synthesize hybrid molecules as kinase inhibitors from these two motifs. In order to study the reactivity of the two active centers in aminorhodanine (N-amino group and the 5-methylene group) toward two carbonyl groups (aromatic aldehyde and ketone of isatin), we decided to carry out a one-pot multi-component reaction by simultaneously introducing aminorhodanine, isatin, and an aromatic aldehyde in ethanol in the presence of AcOEt. Under these conditions, this reaction led to a single adduct. The reaction product structure was confirmed by 1H, 13C-NMR, X-ray single crystal analysis, and high-resolution mass HRMS analysis. As a result, the method used has been very effective and totally stereo- and regioselective. Full article
(This article belongs to the Special Issue Molecules from Multicomponent Reactions)
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4 pages, 348 KiB  
Short Note
Ethyl 4-(2-fluorophenyl)-6-methyl-2-thioxo-1-(p-tolyl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate
by Itamar Luís Gonçalves, Luciano Porto Kagami, Gustavo Machado das Neves, Liliana Rockenbach, Leonardo Davi, Alceu Felipe Soares, Solange Cristina Garcia and Vera Lucia Eifler-Lima
Molbank 2018, 2018(4), M1029; https://doi.org/10.3390/M1029 - 13 Nov 2018
Cited by 1 | Viewed by 3036
Abstract
The Biginelli reaction is a highly versatile reaction that leads to dihydropyrimidinones/thiones. This scaffold is reported as being a privileged structure due to its ability to interact with biological targets. Synthesis of ethyl 4-(2-fluorophenyl)-6-methyl-2-thioxo-1-(p-tolyl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate was achieved through the Biginelli reaction using [...] Read more.
The Biginelli reaction is a highly versatile reaction that leads to dihydropyrimidinones/thiones. This scaffold is reported as being a privileged structure due to its ability to interact with biological targets. Synthesis of ethyl 4-(2-fluorophenyl)-6-methyl-2-thioxo-1-(p-tolyl)-1,2,3,4-tetrahydropyrimidine-5-carboxylate was achieved through the Biginelli reaction using a functionalized thiourea. In silico studies demonstrated that the compound title showed good potential for interacting with ecto-5’-nucleotidase, which has been considered as a target in designs for anti-cancer drugs. Full article
(This article belongs to the Special Issue Molecules from Multicomponent Reactions)
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