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Sustainable Synthesis
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Sustainable Synthesis

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

Deadline for manuscript submissions: closed (28 February 2019) | Viewed by 35938

Special Issue Editor

Prof. Dr. Wei Zhang

E-Mail Website
Guest Editor
Center for Green Chemistry, Department of Chemistry, University of Massachusetts Boston, 100 Morrissey Boulevard, Boston, MA 02125, USA
Interests: green chemistry; organofluorine chemistry; free-radical chemistry; organocatalysis; medicinal chemistry
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

The aim of the development of green and sustainable chemistry is to maximize the benefit of chemistry and chemical products introduced to human society, and minimize their side effects on the environment and public health. This Special Issue presents recent developments on green and sustainable techniques for organic synthesis. It covers following four areas: 1) catalysis reactions (metal-catalysis, organocatalysis, and biocatalysis; 2) new reactions and techniques (pot/atom/step economy reactions, C-H functionalization, flow chemistry, microwave, ultrasonic, photolysis, photoredox, mechanochemistry); 3) alternative solvents (biorenewable solvents, aqueous, ionic liquids, SC-CO2); and 4) CO2 and biomass-derived building blocks for synthesis.

Prof. Wei Zhang
Guest Editor

Manuscript Submission Information

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Keywords

  • Pot, atom and step economic (SPAE) synthesis
  • One-pot reactions
  • Multicomponent reactions
  • Cascade reactions
  • Alternative solvents
  • Biorenewable solvents
  • Solvent-free reactions
  • Metal catalysis
  • Biocatalysis
  • Organocatalysis
  • C-H activation
  • Biomass-derived building blocks
  • CO2 as a synthon
  • Photoredox reactions
  • Photo reactions
  • Microwave reactions
  • Ultrasound reactions
  • Recyclable reagents and catalysts
  • Flow chemistry
  • Mechanochemistry

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Published Papers (7 papers)

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Research

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19 pages, 5818 KiB  
Article
Microwave-Assisted Synthesis of Trazodone and Its Derivatives as New 5-HT1A Ligands: Binding and Docking Studies
by Jolanta Jaśkowska, Przemysław Zaręba, Paweł Śliwa, Edyta Pindelska, Grzegorz Satała and Zbigniew Majka
Molecules 2019, 24(8), 1609; https://doi.org/10.3390/molecules24081609 - 23 Apr 2019
Cited by 22 | Viewed by 5927
Abstract
Trazodone, a well-known antidepressant drug widely used throughout the world, works as a 5-hydroxytryptamine (5-HT2) and α1-adrenergic receptor antagonist and a serotonin reuptake inhibitor. Our research aimed to develop a new method for the synthesis of trazodone and its [...] Read more.
Trazodone, a well-known antidepressant drug widely used throughout the world, works as a 5-hydroxytryptamine (5-HT2) and α1-adrenergic receptor antagonist and a serotonin reuptake inhibitor. Our research aimed to develop a new method for the synthesis of trazodone and its derivatives. In the known methods of the synthesis of trazodone and its derivatives, organic and toxic solvents are used, and the synthesis time varies from several to several dozen hours. Our research shows that trazodone and its derivatives can be successfully obtained in the presence of potassium carbonate as a reaction medium in the microwave field in a few minutes. As a result of the research work, 17 derivatives of trazodone were obtained, including compounds that exhibit the characteristics of 5-HT1A receptor ligands. Molecular modeling studies were performed to understand the differences in the activity toward 5-HT1A and 5-HT2A receptors between ligand 10a (2-(6-(4-(3-chlorophenyl)piperazin-1-yl)hexyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one) (5-HT1A Ki = 16 nM) and trazodone. The docking results indicate the lack of the binding of ligand 10a to 5-HT2AR, which is consistent with the in vitro studies. On the other hand, the docking results for the 5-HT1A receptor indicate two possible binding modes. Crystallographic studies support the hypothesis of an extended conformation. Full article
(This article belongs to the Special Issue Sustainable Synthesis)
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7 pages, 1450 KiB  
Communication
One-Pot Synthesis of Triazolobenzodiazepines Through Decarboxylative [3 + 2] Cycloaddition of Nonstabilized Azomethine Ylides and Cu-Free Click Reactions
by Xiaoming Ma, Xiaofeng Zhang, Weiqi Qiu, Wensheng Zhang, Bruce Wan, Jason Evans and Wei Zhang
Molecules 2019, 24(3), 601; https://doi.org/10.3390/molecules24030601 - 8 Feb 2019
Cited by 23 | Viewed by 4454
Abstract
A one-pot synthesis of triazolobenzodiazepine-containing polycyclic compounds is introduced. The reaction process involves a decarboxylative three-component [3 + 2] cycloaddition of nonstabilized azomethine ylides, N-propargylation, and intramolecular click reactions. Full article
(This article belongs to the Special Issue Sustainable Synthesis)
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12 pages, 21145 KiB  
Article
Ionic Liquid-Promoted Three-Component Domino Reaction of Propargyl Alcohols, Carbon Dioxide and 2-Aminoethanols: A Thermodynamically Favorable Synthesis of 2-Oxazolidinones
by Shumei Xia, Yu Song, Xuedong Li, Hongru Li and Liang-Nian He
Molecules 2018, 23(11), 3033; https://doi.org/10.3390/molecules23113033 - 20 Nov 2018
Cited by 16 | Viewed by 4633
Abstract
To circumvent the thermodynamic limitation of the synthesis of oxazolidinones starting from 2-aminoethanols and CO2 and realize incorporation CO2 under atmospheric pressure, a protic ionic liquid-facilitated three-component reaction of propargyl alcohols, CO2 and 2-aminoethanols was developed to produce 2-oxazolidinones along [...] Read more.
To circumvent the thermodynamic limitation of the synthesis of oxazolidinones starting from 2-aminoethanols and CO2 and realize incorporation CO2 under atmospheric pressure, a protic ionic liquid-facilitated three-component reaction of propargyl alcohols, CO2 and 2-aminoethanols was developed to produce 2-oxazolidinones along with equal amount of α-hydroxyl ketones. The ionic liquid structure, reaction temperature and reaction time were in detail investigated. And 15 mol% 1,5,7-triazabicylo[4.4.0]dec-5-ene ([TBDH][TFE]) trifluoroethanol was found to be able to synergistically activate the substrate and CO2, thus catalyzing this cascade reaction under atmospheric CO2 pressure. By employing this task-specific ionic liquid as sustainable catalyst, 2-aminoethanols with different substituents were successfully transformed to 2-oxazolidinones with moderate to excellent yield after 12 h at 80 °C. Full article
(This article belongs to the Special Issue Sustainable Synthesis)
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10 pages, 2323 KiB  
Article
Synthesis of 1-(para-methoxyphenyl)tetrazolyl-Substituted 1,2,3,4-Tetrahydroisoquinolines and Their Transformations Involving Activated Alkynes
by Alexander A. Titov, Reza Samavati, Elena V. Alexandrova, Tatiana N. Borisova, Tuyet Anh Dang Thi, Van Tuyen Nguyen, Tuan Anh Le, Alexey V. Varlamov, Erik V. Van der Eycken and Leonid G. Voskressensky
Molecules 2018, 23(11), 3010; https://doi.org/10.3390/molecules23113010 - 17 Nov 2018
Cited by 3 | Viewed by 3222
Abstract
1-(p-Methoxyphenyl)tetrazolyl-substituted 6,7-dimethoxy(6,7-methylenedioxy)-1,2,3,4-tetrahydroisoquinolines formed tetrazolyl-substituted azocines in high yields by using activated alkynes. Unsubstituted at 6,7,8-aromatic fragment 1-tetrazolylisoquinoline interacted in several pathways forming tetrazolyl-substituted azocines, 1-tetrazolyl-1-R-vinylisoquinolines and 3-azaspiro[5.5]undeca-1,7,9-triene. Full article
(This article belongs to the Special Issue Sustainable Synthesis)
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18 pages, 4587 KiB  
Article
Immobilized Gold Nanoparticles Prepared from Gold(III)-Containing Ionic Liquids on Silica: Application to the Sustainable Synthesis of Propargylamines
by Raquel Soengas, Yolanda Navarro, María José Iglesias and Fernando López-Ortiz
Molecules 2018, 23(11), 2975; https://doi.org/10.3390/molecules23112975 - 14 Nov 2018
Cited by 18 | Viewed by 4046
Abstract
A cycloaurated phosphinothioic amide gold(III) complex was supported on amorphous silica with the aid of an imidazolium ionic liquid (IL) physisorbed in the SiO2 pores (SiO2–IL) and covalently bonded to the SiO2 (SiO2@IL). Gold(0) nanoparticles (AuNPs) were [...] Read more.
A cycloaurated phosphinothioic amide gold(III) complex was supported on amorphous silica with the aid of an imidazolium ionic liquid (IL) physisorbed in the SiO2 pores (SiO2–IL) and covalently bonded to the SiO2 (SiO2@IL). Gold(0) nanoparticles (AuNPs) were formed in situ and subsequently immobilized on the SiO2–IL/SiO2@IL phase. The resulting catalytic systems Au–SiO2–IL and Au–SiO2@IL promoted the solvent-free A3 coupling reaction of alkynes, aldehydes, and amines in high yields under solvent-free conditions with very low catalyst loading and without the use of additives. The Au–SiO2@IL catalyst showed good recyclability and could be reused at least five times with yields of propargylamines of ≥80%. This synthetic method provides a green and low cost way to effectively prepare propargylamines. Additionally, 31P high resolution magic angle spinning (HRMAS) NMR spectroscopy is introduced as a simple technique to establish the Au loading of the catalyst. Full article
(This article belongs to the Special Issue Sustainable Synthesis)
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17 pages, 4023 KiB  
Article
Esterification of Aryl/Alkyl Acids Catalysed by N-bromosuccinimide under Mild Reaction Conditions
by Klara Čebular, Bojan Đ. Božić and Stojan Stavber
Molecules 2018, 23(9), 2235; https://doi.org/10.3390/molecules23092235 - 2 Sep 2018
Cited by 10 | Viewed by 7575
Abstract
N-halosuccinimides (NXSs) are well-known to be convenient, easily manipulable and low-priced halogenation reagents in organic synthesis. In the present work, N-bromosuccinimide (NBS) has been promoted as the most efficient and selective catalyst among the NXSs in the reaction of direct esterification [...] Read more.
N-halosuccinimides (NXSs) are well-known to be convenient, easily manipulable and low-priced halogenation reagents in organic synthesis. In the present work, N-bromosuccinimide (NBS) has been promoted as the most efficient and selective catalyst among the NXSs in the reaction of direct esterification of aryl and alkyl carboxylic acids. Comprehensive esterification of substituted benzoic acids, mono-, di- and tri-carboxy alkyl derivatives has been performed under neat reaction conditions. The method is metal-free, air- and moisture-tolerant, allowing for a simple synthetic and isolation procedure as well as the large-scale synthesis of aromatic and alkyl esters with yields up to 100%. Protocol for the recycling of the catalyst has been proposed. Full article
(This article belongs to the Special Issue Sustainable Synthesis)
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Review

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32 pages, 19004 KiB  
Review
Organophosphine-Catalyzed [4C+X] Annulations
by Yangyan Li, Xiang Chen, Xiaoming Chen and Xiao Shen
Molecules 2018, 23(11), 3022; https://doi.org/10.3390/molecules23113022 - 19 Nov 2018
Cited by 9 | Viewed by 4552
Abstract
In recent years, there have been extraordinary developments of organophosphine-catalyzed reactions. This includes progress in the area of [4C+X] annulations, which are of particular interest due to their potential for the rapid construction of 5–8-membered cyclic products. In this short overview, we summarize [...] Read more.
In recent years, there have been extraordinary developments of organophosphine-catalyzed reactions. This includes progress in the area of [4C+X] annulations, which are of particular interest due to their potential for the rapid construction of 5–8-membered cyclic products. In this short overview, we summarize the remarkable progress, emphasizing reaction mechanisms and key intermediates involved in the processes. The discussion is classified according to the type of electrophilic reactants that acted as C4 synthons in the annulation process, in the order of α-alkyl allenoates, γ-alkyl allenoates, α-methyl allene ketones, β′-OAc allenoate, δ-OAc allenoate, activated dienes and cyclobutenones. Full article
(This article belongs to the Special Issue Sustainable Synthesis)
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Scheme 1

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