Search for Articles:
Title / Keyword
Author / Affiliation / Email
Journal
Article Type
 
 
Advanced Search
 
Section
Special Issue
Volume
Issue
Number
Page
 
7.4
4.2
Journals
Molecules
Special Issues
Multicomponent Reaction
molecules-logo
Submit to Molecules Review for Molecules Propose a Special Issue

Journal Menu

► Journal Menu

Journal Browser

► Journal Browser
share announcement

Multicomponent Reaction

A special issue of Molecules (ISSN 1420-3049).

Deadline for manuscript submissions: closed (30 December 2012) | Viewed by 77353

Special Issue Editor

Dr. Irini Akritopoulou-Zanze

E-Mail
Guest Editor
Global Pharmaceutical Research and Development, Abbott Laboratories, 100 Abbott Park Road, Abbott Park, IL 60064-3500, USA
Interests: drug discovery; de novo design and synthesis of biologically active scaffolds; focused compound libraries; multicomponent reactions

Special Issue Information

Dear Colleagues,

Multicomponent reactions (MCRs) are powerful transformations that incorporate portions of three or more reactants into new products in one pot procedures. They have been used extensively to form heterocyclic structures and they have been combined with subsequent transformations to yield complex structures, not easily accessible via classical synthetic reactions.
Efforts to discover new MCRs or further develop older ones, especially in combination with other transformations, contribute significantly to the advancement of organic synthesis by providing greater flexibility, novelty and efficiency. Applications of MCRs in drug discovery, material sciences, natural product synthesis and ligand and biological probe preparations further demonstrate the power of these reactions. Advances in cheminformatic tools allow for virtual MCR libraries to be first accessed in silico against a variety of different parameters before initiation of compound library synthesis.

This special issue of Molecules welcomes previously unpublished manuscripts covering all aspects of multicomponent reactions including their design, product assessment, methodology development and applications.

Dr. Irini Akritopoulou-Zanze
Guest Editor

Keywords

  • multicomponent reactions
  • isocyanide-based MCRS
  • heterocycle forming MCRS
  • library design
  • library synthesis
  • parallel synthesis
  • novel scaffolds
  • biologically active molecules
  • post MCR transformations
  • macromolecules

Benefits of Publishing in a Special Issue

  • Ease of navigation: Grouping papers by topic helps scholars navigate broad scope journals more efficiently.
  • Greater discoverability: Special Issues support the reach and impact of scientific research. Articles in Special Issues are more discoverable and cited more frequently.
  • Expansion of research network: Special Issues facilitate connections among authors, fostering scientific collaborations.
  • External promotion: Articles in Special Issues are often promoted through the journal's social media, increasing their visibility.
  • Reprint: MDPI Books provides the opportunity to republish successful Special Issues in book format, both online and in print.

Further information on MDPI's Special Issue policies can be found here.

Published Papers (9 papers)

Download All Papers
Order results
Result details
Show export options expand_more Show export options expand_less
Select all
Export citation of selected articles as:

Research

Jump to: Review

15 pages, 333 KiB  
Article
One-Pot Ugi/Aza-Michael Synthesis of Highly Substituted 2,5-Diketopiperazines with Anti-Proliferative Properties
by Andreas Hartung, Florian Seufert, Carsten Berges, Viktoria H. Gessner and Ulrike Holzgrabe
Molecules 2012, 17(12), 14685-14699; https://doi.org/10.3390/molecules171214685 - 11 Dec 2012
Cited by 17 | Viewed by 6829
Abstract
The well-known Ugi reaction of aldehydes with amines, carboxylic acids and isocyanides leads to the formation of acyclic α-acylaminocarboxamides. Replacement of the carboxylic acid derivatives with β-acyl substituted acrylic acids gives access to highly substituted 2,5-diketopiperazines in one single reaction-step without additives or [...] Read more.
The well-known Ugi reaction of aldehydes with amines, carboxylic acids and isocyanides leads to the formation of acyclic α-acylaminocarboxamides. Replacement of the carboxylic acid derivatives with β-acyl substituted acrylic acids gives access to highly substituted 2,5-diketopiperazines in one single reaction-step without additives or complex reaction procedures. The obtained diketopiperazines show anti-proliferative effects on activated T cells and represent therefore potential candidates for targeting unwanted T cell-mediated immune responses. Full article
(This article belongs to the Special Issue Multicomponent Reaction)
►▼ Show Figures

Graphical abstract

11 pages, 259 KiB  
Communication
Multicomponent Synthesis of 3,6-Dihydro-2H-1,3-thiazine-2-thiones
by Art Kruithof, Marten L. Ploeger, Elwin Janssen, Madeleine Helliwell, Frans J. J. de Kanter, Eelco Ruijter and Romano V. A. Orru
Molecules 2012, 17(2), 1675-1685; https://doi.org/10.3390/molecules17021675 - 8 Feb 2012
Cited by 20 | Viewed by 6354
Abstract
Non-fused 3,6-dihydro-2H-1,3-thiazine-2-thiones constitute a so far rather unexplored class of compounds, with the latest report dating back more than two decades. Thiazine-2-thiones contain an endocyclic dithiocarbamate group, which is often found in pesticides, in substrates for radical chemistry and in synthetic [...] Read more.
Non-fused 3,6-dihydro-2H-1,3-thiazine-2-thiones constitute a so far rather unexplored class of compounds, with the latest report dating back more than two decades. Thiazine-2-thiones contain an endocyclic dithiocarbamate group, which is often found in pesticides, in substrates for radical chemistry and in synthetic intermediates towards thioureas and amidines. We now report the multicomponent reaction (MCR) of in situ-generated 1-azadienes with carbon disulfide. With this reaction, a one-step protocol towards the potentially interesting 3,6-dihydro-2H-1,3-thiazine-2-thiones was established and a small library was synthesized. Full article
(This article belongs to the Special Issue Multicomponent Reaction)
►▼ Show Figures

Graphical abstract

17 pages, 424 KiB  
Article
Prebiotic Activity of Polysaccharides Extracted from Gigantochloa Levis (Buluh beting) Shoots
by Aida Firdaus Muhammad Nurul Azmi, Shuhaimi Mustafa, Dzulkifly Md. Hashim and Yazid Abdul Manap
Molecules 2012, 17(2), 1635-1651; https://doi.org/10.3390/molecules17021635 - 7 Feb 2012
Cited by 105 | Viewed by 10369
Abstract
Bamboo shoot crude polysaccharides (BSCP) extracted from the shoots of Gigantochloa levis gave about 3.27 ± 0.18% on dry basis and a very minute percentage of protein (0.02 ± 0.01%). The molecular weight of BSCP estimated by gel chromatography was found to be [...] Read more.
Bamboo shoot crude polysaccharides (BSCP) extracted from the shoots of Gigantochloa levis gave about 3.27 ± 0.18% on dry basis and a very minute percentage of protein (0.02 ± 0.01%). The molecular weight of BSCP estimated by gel chromatography was found to be around 7.49 × 103 Da, while the molecular weights of purified fractions (F1 to F5) were around 1550.96, 1471.63, 1685.78, 1691.61 and 1551.67 Da, respectively. The FTIR spectrum of BSCP revealed the possibility that the extract contains β-glucan, which can be considered a valuable compound for the medical and food industries. These relate to the resistance of BSCP towards artificial human gastric juice which is more than 99%. Prebiotic activity tested using BSCP as a carbon source showed significant increase in the growth of B. animalis ATCC 1053, B. longum BB 536 and L. acidophilus ATCC 4356 as compared to the use of FOS. Survivality of S. choleraesuis JCM 6977 was found to be slower in both BSCP and FOS. Study conducted reflects a good sign for the BSCP to be exploited as a promising prebiotic. Full article
(This article belongs to the Special Issue Multicomponent Reaction)
►▼ Show Figures

Figure 1

17 pages, 373 KiB  
Communication
Consecutive Three-Component Synthesis of 3-(Hetero)Aryl-1H-pyrazoles with Propynal Diethylacetal as a Three-Carbon Building Block
by Lucilla Levi, Christina Boersch, Charlotte F. Gers, Eugen Merkul and Thomas J. J. Müller
Molecules 2011, 16(11), 9340-9356; https://doi.org/10.3390/molecules16119340 - 7 Nov 2011
Cited by 13 | Viewed by 7404
Abstract
A novel consecutive three-component synthesis of 3-(hetero)aryl-1H-pyrazoles via room temperature Sonogashira arylation of propynal diethylacetal used as a propargyl aldehyde synthetic equivalent has been disclosed. The final acetal cleavage-cyclocondensation with hydrazine hydrochloride at 80 °C rapidly furnishes the title compounds in [...] Read more.
A novel consecutive three-component synthesis of 3-(hetero)aryl-1H-pyrazoles via room temperature Sonogashira arylation of propynal diethylacetal used as a propargyl aldehyde synthetic equivalent has been disclosed. The final acetal cleavage-cyclocondensation with hydrazine hydrochloride at 80 °C rapidly furnishes the title compounds in a one-pot fashion. Full article
(This article belongs to the Special Issue Multicomponent Reaction)
►▼ Show Figures

Graphical abstract

13 pages, 412 KiB  
Article
Xanthate Based Radical Cascade Toward Multicomponent Formation of Pyrrolopyrimidines
by Laurent El Kaïm, Laurence Grimaud and Patil Pravin
Molecules 2011, 16(11), 9261-9273; https://doi.org/10.3390/molecules16119261 - 4 Nov 2011
Cited by 9 | Viewed by 6489
Abstract
A short sequential synthesis of pyrrolidino- pyridines and pyrimidines illustrates the potential of combining Ugi-Smiles couplings with radical tin-free processes. Full article
(This article belongs to the Special Issue Multicomponent Reaction)
►▼ Show Figures

Figure 1

17 pages, 174 KiB  
Article
Small Molecule Library Synthesis Using Segmented Flow
by Christina M. Thompson, Jennifer L. Poole, Jeffrey L. Cross, Irini Akritopoulou-Zanze and Stevan W. Djuric
Molecules 2011, 16(11), 9161-9177; https://doi.org/10.3390/molecules16119161 - 2 Nov 2011
Cited by 28 | Viewed by 8714
Abstract
Flow chemistry has gained considerable recognition as a simple, efficient, and safe technology for the synthesis of many types of organic and inorganic molecules ranging in scope from large complex natural products to silicon nanoparticles. In this paper we describe a method that [...] Read more.
Flow chemistry has gained considerable recognition as a simple, efficient, and safe technology for the synthesis of many types of organic and inorganic molecules ranging in scope from large complex natural products to silicon nanoparticles. In this paper we describe a method that adapts flow chemistry to the synthesis of libraries of compounds using a fluorous immiscible solvent as a spacer between reactions. The methodology was validated in the synthesis of two small heterocycle containing libraries. The reactions were performed on a 0.2 mmol scale, enabling tens of milligrams of material to be generated in a single 200 mL reaction plug. The methodology allowed library synthesis in half the time of conventional microwave synthesis while maintaining similar yields. The ability to perform multiple, potentially unrelated reactions in a single run is ideal for making small quantities of many different compounds quickly and efficiently. Full article
(This article belongs to the Special Issue Multicomponent Reaction)
►▼ Show Figures

Figure 1

18 pages, 343 KiB  
Article
Studies on the Synthesis of DMAP Derivatives by Diastereoselective Ugi Reactions
by Hiroki Mandai, Shunsuke Irie, Koichi Mitsudo and Seiji Suga
Molecules 2011, 16(10), 8815-8832; https://doi.org/10.3390/molecules16108815 - 20 Oct 2011
Cited by 27 | Viewed by 10586
Abstract
Diastereoselective Ugi reactions of DMAP-based aldehydes with α-amino acids and tert-butyl isocyanide were examined. The reactions of 4-(dimethylamino)-2-pyridine-carboxaldehyde with various α-amino acids afforded 2-substituted DMAP derivatives with low diastereoselectivity. On the contrary, reactions with 4-(dimethylamino)-3-pyridine-carboxaldehyde delivered 3-substituted DMAP derivatives with moderate to [...] Read more.
Diastereoselective Ugi reactions of DMAP-based aldehydes with α-amino acids and tert-butyl isocyanide were examined. The reactions of 4-(dimethylamino)-2-pyridine-carboxaldehyde with various α-amino acids afforded 2-substituted DMAP derivatives with low diastereoselectivity. On the contrary, reactions with 4-(dimethylamino)-3-pyridine-carboxaldehyde delivered 3-substituted DMAP derivatives with moderate to high diastereoselectivity. The combination of α-amino acid and DMAP-based aldehyde is thus important to achieve high diastereoselectivity. Kinetic resolution of a secondary alcohol using a chiral DMAP derivative obtained through these reactions was also examined. Full article
(This article belongs to the Special Issue Multicomponent Reaction)
►▼ Show Figures

Figure 1

13 pages, 237 KiB  
Article
Divergent Synthesis of Novel Five-Membered Heterocyclic Compounds by Base-Mediated Rearrangement of Acrylamides Derived from a Novel Isocyanide-Based Multicomponent Reaction
by Andrea Basso, Luca Banfi and Renata Riva
Molecules 2011, 16(10), 8775-8787; https://doi.org/10.3390/molecules16108775 - 19 Oct 2011
Cited by 17 | Viewed by 7133
Abstract
We have recently reported a novel multicomponent reaction between arylacetic acids and isocyanides, affording α-acyloxyacrylamides through an unusual mechanism. The products of this novel multicomponent reaction can rearrange to five membered heterocyclic compounds when exposed to an alkaline environment. Depending on the reaction [...] Read more.
We have recently reported a novel multicomponent reaction between arylacetic acids and isocyanides, affording α-acyloxyacrylamides through an unusual mechanism. The products of this novel multicomponent reaction can rearrange to five membered heterocyclic compounds when exposed to an alkaline environment. Depending on the reaction conditions and on the substitution pattern on the substrates, various pyrrolidine derivatives can be selectively obtained. We now wish to report that libraries endowed with skeletal diversity, thus responding to the requirements of Diversity Oriented Synthesis (DOS), can be efficiently prepared in this manner, and phenotypic biological assays have shown interesting properties of some representative compounds. Full article
(This article belongs to the Special Issue Multicomponent Reaction)
►▼ Show Figures

Graphical abstract

Review

Jump to: Research

29 pages, 964 KiB  
Review
Diversity Oriented Syntheses of Conventional Heterocycles by Smart Multi Component Reactions (MCRs) of the Last Decade
by Heiner Eckert
Molecules 2012, 17(1), 1074-1102; https://doi.org/10.3390/molecules17011074 - 20 Jan 2012
Cited by 156 | Viewed by 12237
Abstract
A collection of smart multicomponent reactions (MCRs) with continuative post condensation cyclizations (PCCs) is presented to construct conventional three- to seven-membered heterocyclic compounds in diversity oriented syntheses (DOS). These will provide a high degree of applying economical and ecological advantages as well as [...] Read more.
A collection of smart multicomponent reactions (MCRs) with continuative post condensation cyclizations (PCCs) is presented to construct conventional three- to seven-membered heterocyclic compounds in diversity oriented syntheses (DOS). These will provide a high degree of applying economical and ecological advantages as well as of practicability. Water, ionic liquids, and solvent-less syntheses as well as use of various forms of energy as microwave and ultrasonic irradiation are examined and discussed. Full article
(This article belongs to the Special Issue Multicomponent Reaction)
►▼ Show Figures

Graphical abstract

Show export options expand_more Show export options expand_less
Select all
Export citation of selected articles as:
 
Displaying articles 1-9
Back to TopTop