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Special Issue "MCRs and Related One-Pot Organic Synthesis"

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

Deadline for manuscript submissions: closed (15 July 2016)

Special Issue Editor

Guest Editor
Prof. Romano V. A. Orru

Department of Chemistry and Pharmaceutical Sciences, VU University Amsterdam, De Boelelaan 1083, 1081 HV Amsterdam, The Netherlands
Website | E-Mail
Phone: 0031205987447
Interests: synthetic methodology; multi component reactions; biocatalysis; natural products

Special Issue Information

Dear Colleagues,

Organic Synthesis is the science of making new, unexplored molecules. From simple building blocks to complex products. This is exactly what is at the heart of this Special Issue of “Molecules”.

Currently, Synthetic Organic chemists are able to design a multistep synthesis for almost any conceivable chemical structure by a rational approach based on the large toolbox of synthetic methods available and a retrosynthetic analysis. Traditionally, the reagents and conditions for each of the reaction steps need to be optimized to give a good yield and a pure product, with as little work as possible. To be useful in organic synthesis, methods must be reliable for a broad range of substrates. For complex organic molecules, however, executing such a “total” synthesis is still far from trivial, and is often neither simple nor elegant. The routes are often lengthy, with many reaction steps, employing a multitude of different, sometimes highly creative, protective group strategies, and/or using “metal-based”-catalysis. Truly sustainable production of complex, highly functionalized molecules for advanced application as (fine) chemicals and pharmaceuticals or in food, in materials, or in catalysis is still beyond any state of maturity. Thus, there is a clear need for the discovery and development of clean, atom- and step-efficient one-pot syntheses for the sustainable production of molecularly diverse and structurally complex organic molecules with high-added-values.

Mulicomponent reactions (MCRs) are increasingly appreciated as efficient synthesis tools to rapidly access complex products. With MCRs, molecules can be assembled from three or more starting materials in a one-pot process. MCRs involve the inherent formation of several bonds in a single operation, without isolating the intermediates, changing the reaction conditions, and often without adding further reagents. Therefore, MCRs address sustainability by atom-, step-, and, thus, eco-efficiency, reducing the number of intermediate steps and functional group manipulations and avoiding protective group strategies. Syntheses involving MCRs save time and energy (step efficiency) and proceed with high convergency (process efficiency). In addition, MCRs are ideally suited for combinatorial chemistry and library design, and are of great utility in medicinal chemistry, material science, recognition (host-guest) chemistry, and catalyst design. Notably, MCRs are believed to be crucial in exploiting the full potential of “diversity-oriented synthesis” (DOS) and “biology-oriented synthesis” (BIOS) design strategies for effective and functional library synthesis uncovering virgin areas of biologically relevant chemical space.

In this Special Issue of Molecules, research articles covering all areas of MCR-chemistry and related one-pot syntheses are welcomed to provide an interesting “snap-shot” of the current state-of-the-art in this exciting organic chemistry research field.

Prof. Romano V. A. Orru
Guest Editor

Manuscript Submission Information

Manuscripts should be submitted online at www.mdpi.com by registering and logging in to this website. Once you are registered, click here to go to the submission form. Manuscripts can be submitted until the deadline. All papers will be peer-reviewed. Accepted papers will be published continuously in the journal (as soon as accepted) and will be listed together on the special issue website. Research articles, review articles as well as short communications are invited. For planned papers, a title and short abstract (about 100 words) can be sent to the Editorial Office for announcement on this website.

Submitted manuscripts should not have been published previously, nor be under consideration for publication elsewhere (except conference proceedings papers). All manuscripts are thoroughly refereed through a single-blind peer-review process. A guide for authors and other relevant information for submission of manuscripts is available on the Instructions for Authors page. Molecules is an international peer-reviewed open access monthly journal published by MDPI.

Please visit the Instructions for Authors page before submitting a manuscript. The Article Processing Charge (APC) for publication in this open access journal is 1800 CHF (Swiss Francs). Submitted papers should be well formatted and use good English. Authors may use MDPI's English editing service prior to publication or during author revisions.


Keywords

  • organic synthesis
  • multicomponent reaction
  • diversity oriented synthesis
  • atom- and step efficiency
  • one-pot reactions
  • cascade reactions

Published Papers (6 papers)

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Research

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Open AccessArticle Thiazine-2-thiones as Masked 1-Azadienes in Cascade Dimerization Reactions)
Molecules 2017, 22(4), 541; doi:10.3390/molecules22040541
Received: 28 February 2017 / Revised: 24 March 2017 / Accepted: 26 March 2017 / Published: 28 March 2017
PDF Full-text (2812 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
We report the unexpected formation of a 1-azadiene dimer from 4,6-diphenyl-3,6-dihydro-2H-1,3-thiazine-2-thiones under prolonged microwave irradiation. In this manner, thiazine-2-thiones act as “masked” 1-azadiene equivalents, which makes them useful synthetic tools to access complex heterocyclic frameworks. We compare this dimerization with earlier
[...] Read more.
We report the unexpected formation of a 1-azadiene dimer from 4,6-diphenyl-3,6-dihydro-2H-1,3-thiazine-2-thiones under prolonged microwave irradiation. In this manner, thiazine-2-thiones act as “masked” 1-azadiene equivalents, which makes them useful synthetic tools to access complex heterocyclic frameworks. We compare this dimerization with earlier approaches and elaborate on the observed diastereoselectivity. Full article
(This article belongs to the Special Issue MCRs and Related One-Pot Organic Synthesis)
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Figure 1

Open AccessArticle Synthesis and Antifungal Activity against Fusarium oxysporum of Some Brassinin Analogs Derived from l-tryptophan: A DFT/B3LYP Study on the Reaction Mechanism
Molecules 2016, 21(10), 1349; doi:10.3390/molecules21101349
Received: 14 September 2016 / Revised: 26 September 2016 / Accepted: 8 October 2016 / Published: 11 October 2016
PDF Full-text (948 KB) | HTML Full-text | XML Full-text
Abstract
An efficient methodology to obtain novel antifungal analogs of brassinin 1 is described. Starting from l-tryptophan 2, N,N′-dialkylthiourea 4, 4-[(1H-indol-3-yl)methylene]-2-sulfanylidene-1,3-thiazolidin-5-one 5 and alkyl (2S)-3-(1H-indol-3-yl)-2-{[(alkylsulfanyl)carbonothioyl]amino}propanoate 6 type compounds were obtained as main
[...] Read more.
An efficient methodology to obtain novel antifungal analogs of brassinin 1 is described. Starting from l-tryptophan 2, N,N′-dialkylthiourea 4, 4-[(1H-indol-3-yl)methylene]-2-sulfanylidene-1,3-thiazolidin-5-one 5 and alkyl (2S)-3-(1H-indol-3-yl)-2-{[(alkylsulfanyl)carbonothioyl]amino}propanoate 6 type compounds were obtained as main products in different ratios depending on the reaction conditions via a tandem dithiocarbamate formation and Michael addition reaction. In order to understand the dependence of the reaction conditions on the mechanism pathway, a DFT/B3LYP study was performed. The results suggested the existence of competitive mechanistic routes which involve the presence of an ionic dithiocarbamate intermediate 9. Antifungal activities of all products were then evaluated against Fusarium oxysporum through mycelial growth inhibition using a microscale amended-medium assay. IC50 values were thus determined for each compound. These results showed that 6-related compounds can be considered as promissory antifungal agents. Full article
(This article belongs to the Special Issue MCRs and Related One-Pot Organic Synthesis)
Figures

Open AccessArticle A Novel and Efficient Five-Component Synthesis of Pyrazole Based Pyrido[2,3-d]pyrimidine-diones in Water: A Triply Green Synthesis
Molecules 2016, 21(4), 441; doi:10.3390/molecules21040441
Received: 25 February 2016 / Revised: 12 March 2016 / Accepted: 24 March 2016 / Published: 1 April 2016
Cited by 1 | PDF Full-text (1012 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
A novel one pot synthesis of pyrazolo[4′,3′:5,6]pyrido[2,3-d]pyrimidine-diones, via a five-component reaction, involving, hydrazine hydrate, ethyl acetoacetate, and 1,3-dimethyl barbituric acid, an appropriate aryl aldehydes and ammonium acetate catalyzed via both of heterogeneous and homogeneous catalysis in water, is reported. Full article
(This article belongs to the Special Issue MCRs and Related One-Pot Organic Synthesis)
Open AccessArticle Multicomponent Synthesis and Evaluation of New 1,2,3-Triazole Derivatives of Dihydropyrimidinones as Acidic Corrosion Inhibitors for Steel
Molecules 2016, 21(2), 250; doi:10.3390/molecules21020250
Received: 23 December 2015 / Revised: 7 February 2016 / Accepted: 17 February 2016 / Published: 22 February 2016
Cited by 5 | PDF Full-text (1591 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
An efficient one-pot synthesis of 1,2,3-triazole derivatives of dihydropyrimidinones has been developed using two multicomponent reactions. The aldehyde-1,2,3-triazoles were obtained in good yields from in situ-generated organic azides and O-propargylbenzaldehyde. The target heterocycles were synthesized through the Biginelli reaction in which
[...] Read more.
An efficient one-pot synthesis of 1,2,3-triazole derivatives of dihydropyrimidinones has been developed using two multicomponent reactions. The aldehyde-1,2,3-triazoles were obtained in good yields from in situ-generated organic azides and O-propargylbenzaldehyde. The target heterocycles were synthesized through the Biginelli reaction in which the aldehyde-1,2,3-triazoles reacted with ethyl acetoacetate and urea in the presence of Ce(OTf)3 as the catalyst. The corrosion inhibition of steel grade API 5 L X52 in 1 M HCl by the synthesized compounds was investigated using the electrochemical impedance spectroscopy technique. The measurements revealed that these heterocycles are promising candidates to inhibit acidic corrosion of steel. Full article
(This article belongs to the Special Issue MCRs and Related One-Pot Organic Synthesis)
Figures

Open AccessArticle An Expedient Regio- and Diastereoselective Synthesis of Hybrid Frameworks with Embedded Spiro[9,10]dihydroanthracene [9,3′]-pyrrolidine and Spiro[oxindole-3,2′-pyrrolidine] Motifs via an Ionic Liquid-Mediated Multicomponent Reaction
Molecules 2015, 20(9), 16142-16153; doi:10.3390/molecules200916142
Received: 8 August 2015 / Revised: 21 August 2015 / Accepted: 24 August 2015 / Published: 3 September 2015
Cited by 4 | PDF Full-text (908 KB) | HTML Full-text | XML Full-text | Supplementary Files
Abstract
A series of hitherto unreported anthracene-embedded dispirooxindoles has been synthesized via a one-pot three-component 1,3-dipolar cycloaddition reaction of an azomethine ylide, generated in situ from the reaction of isatin and sarcosine to 10-benzylideneanthracen-9(10H)-one as a dipolarophile in 1-butyl-3-methylimidazolium bromide([bmim]Br), an ionic
[...] Read more.
A series of hitherto unreported anthracene-embedded dispirooxindoles has been synthesized via a one-pot three-component 1,3-dipolar cycloaddition reaction of an azomethine ylide, generated in situ from the reaction of isatin and sarcosine to 10-benzylideneanthracen-9(10H)-one as a dipolarophile in 1-butyl-3-methylimidazolium bromide([bmim]Br), an ionic liquid. This reaction proceeded regio- and diastereoselectively, in good to excellent yields. Full article
(This article belongs to the Special Issue MCRs and Related One-Pot Organic Synthesis)
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Review

Jump to: Research

Open AccessReview Isocyanide-Based Multicomponent Reactions for the Synthesis of Heterocycles
Molecules 2016, 21(1), 19; doi:10.3390/molecules21010019
Received: 10 October 2015 / Revised: 2 December 2015 / Accepted: 17 December 2015 / Published: 23 December 2015
Cited by 13 | PDF Full-text (5910 KB) | HTML Full-text | XML Full-text
Abstract
Multicomponent reactions (MCRs) are extremely popular owing to their facile execution, high atom-efficiency and the high diversity of products. MCRs can be used to access various heterocycles and highly functionalized scaffolds, and thus have been invaluable tools in total synthesis, drug discovery and
[...] Read more.
Multicomponent reactions (MCRs) are extremely popular owing to their facile execution, high atom-efficiency and the high diversity of products. MCRs can be used to access various heterocycles and highly functionalized scaffolds, and thus have been invaluable tools in total synthesis, drug discovery and bioconjugation. Traditional isocyanide-based MCRs utilize an external nucleophile attacking the reactive nitrilium ion, the key intermediate formed in the reaction of the imine and the isocyanide. However, when reactants with multiple nucleophilic groups (bisfunctional reactants) are used in the MCR, the nitrilium intermediate can be trapped by an intramolecular nucleophilic attack to form various heterocycles. The implications of nitrilium trapping along with widely applied conventional isocyanide-based MCRs in drug design are discussed in this review. Full article
(This article belongs to the Special Issue MCRs and Related One-Pot Organic Synthesis)
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