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Multicomponent Reactions
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Multicomponent Reactions

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

Deadline for manuscript submissions: closed (31 March 2019) | Viewed by 35047

Special Issue Editor

Dr. Cimarelli Cristina

E-Mail Website
Guest Editor
School of Science and Technology, Chemistry Division, University of Camerino, Camerino, Italy
Interests: stereoselective synthesis; Lewis acid catalysis; multicomponent reactions; small molecules; heterocycle synthesis; green chemistry
Special Issues, Collections and Topics in MDPI journals

Special Issue Information

Dear Colleagues,

Multicomponent reactions share many features that make them very appealing to organic chemists. According to a commonly-accepted definition, “MCRs are reactions with three and more starting materials where the majority of the atoms of the starting material are incorporated in the product”. MCRs start mixing three or more reagents, continue in one-pot fashion through several reaction steps without human intervention to isolate and separate intermediates and converge on a final product, which, in almost all cases, contains all the atoms of the starting material, with little or no side products. They appear to be ideal for any form of synthesis, because of their high atom economy and bond-forming efficiency, low-cost separation and purification of products, and scarce waste formation. Futhermore they offer the possibility to produce molecular diversity in combinatorial synthesis, and, in many cases, may be adapted to automation. Furthermore, from a purely academic point of view, all multicomponent reactions involve a plethora of chemical reactions, offering the possibility to study many beautiful and interesting chemistry.

Many fields of organic chemistry have been taking advantage of multicomponent reactions; thus, selected papers are welcomed that open new perspectives in MCR chemistry with creative results, and in MCRs applications to the synthesis of various classes of organic compounds, not only in organic synthesis and drug discovery, but also in material science, agriculture, medical devices, imaging, or in other fields, such as solar energy, stem cell therapy or superconductivity.

Dr. Cimarelli Cristina
Guest Editor

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Keywords

  • multicomponent reactions
  • small molecules
  • heterocycle synthesis
  • green chemistry
  • synthetic methodologies

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Published Papers (8 papers)

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Editorial

Jump to: Research, Review

2 pages, 163 KiB  
Editorial
Multicomponent Reactions
by Cristina Cimarelli
Molecules 2019, 24(13), 2372; https://doi.org/10.3390/molecules24132372 - 27 Jun 2019
Cited by 42 | Viewed by 4004
Abstract
Multicomponent Reactions appear to be ideal for any form of synthesis, because of their numerous advantages in terms of sustainability and selectivity in building up complex molecular architectures, with high molecular diversity. This Special Issue collects seven contributions which expand our knowledge about [...] Read more.
Multicomponent Reactions appear to be ideal for any form of synthesis, because of their numerous advantages in terms of sustainability and selectivity in building up complex molecular architectures, with high molecular diversity. This Special Issue collects seven contributions which expand our knowledge about Multicomponent Reactions, providing a good overview about innovative reactivities and applications. Full article
(This article belongs to the Special Issue Multicomponent Reactions)

Research

Jump to: Editorial, Review

13 pages, 1632 KiB  
Article
Microwave-Assisted Kabachnik–Fields Reaction with Amino Alcohols as the Amine Component
by Ádám Tajti, Enikő Szatmári, Franc Perdih, György Keglevich and Erika Bálint
Molecules 2019, 24(8), 1640; https://doi.org/10.3390/molecules24081640 - 25 Apr 2019
Cited by 13 | Viewed by 3607
Abstract
In this paper, the microwave (MW)-assisted catalyst-free and mostly solvent-free Kabachnik–Fields reaction of amino alcohols, paraformaldehyde, and various >P(O)H reagents (dialkyl phosphites, ethyl phenyl-H-phosphinate, and secondary phosphine oxides) is reported. The synthesis of N-2-hydroxyethyl-α-aminophosphonate derivatives was optimized in respect of [...] Read more.
In this paper, the microwave (MW)-assisted catalyst-free and mostly solvent-free Kabachnik–Fields reaction of amino alcohols, paraformaldehyde, and various >P(O)H reagents (dialkyl phosphites, ethyl phenyl-H-phosphinate, and secondary phosphine oxides) is reported. The synthesis of N-2-hydroxyethyl-α-aminophosphonate derivatives was optimized in respect of the temperature, the reaction time, and the molar ratio of the starting materials. A few by-products were also identified. N,N-Bis(phosphinoylmethyl)amines containing a hydroxyethyl group were also prepared by the double Kabachnik–Fields reaction of ethanolamine with an excess of paraformaldehyde and secondary phosphine oxides. The crystal structure of a 2-hydroxyethyl-α-aminophosphine oxide and a bis(phosphinoylmethyl)ethanolamine was studied by X-ray analysis. Full article
(This article belongs to the Special Issue Multicomponent Reactions)
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15 pages, 1765 KiB  
Article
MCR Scaffolds Get Hotter with 18F-Labeling
by Tryfon Zarganes-Tzitzikas, Gonçalo S. Clemente, Philip H. Elsinga and Alexander Dömling
Molecules 2019, 24(7), 1327; https://doi.org/10.3390/molecules24071327 - 4 Apr 2019
Cited by 22 | Viewed by 4448
Abstract
Imaging techniques, such as positron emission tomography (PET), represent great progress in the clinical development of drugs and diagnostics. However, the efficient and timely synthesis of appropriately labeled compounds is a largely unsolved problem. Numerous small drug-like molecules with high structural diversity can [...] Read more.
Imaging techniques, such as positron emission tomography (PET), represent great progress in the clinical development of drugs and diagnostics. However, the efficient and timely synthesis of appropriately labeled compounds is a largely unsolved problem. Numerous small drug-like molecules with high structural diversity can be synthesized via convergent multicomponent reactions (MCRs). The combination of PET labeling with MCR synthesis of biologically active compounds can greatly simplify radioanalytical and imaging-based analysis. In a proof-of-concept study, we optimized robust on-site radiolabeling conditions that were subsequently applied to several structurally different drug-like MCR scaffolds (e.g., arenes, β-lactam, tetrazole, and oxazole). These labeled scaffolds were synthesized via pinacol-derived aryl boronic esters (arylBPin) by copper-mediated oxidative 18F-fluorination with radiochemical conversions (RCCs) from 15% to 76%. Full article
(This article belongs to the Special Issue Multicomponent Reactions)
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10 pages, 8430 KiB  
Article
A Simple and Efficient Synthesis of Highly Substituted Indeno[1,2-b]pyrrole and Acenaphtho[1,2-b]pyrrole Derivatives by Tandem Three-Component Reactions
by Xiaodong Tang, Songlei Zhu, Ying Ma, Ren Wen, Lanqi Cen, Panwei Gong and Jing Wang
Molecules 2018, 23(11), 3031; https://doi.org/10.3390/molecules23113031 - 20 Nov 2018
Cited by 12 | Viewed by 3507
Abstract
A green, convenient and tandem procedure for the efficient synthesis of highly substituted indeno[1,2-b]pyrrole and acenaphtho[1,2-b]pyrrole derivatives by domino three-component reaction of tryptamine/benzylamine, 1,3-dicarbonyl compounds and ninhydrin/ acenaphthenequinone is described. The significant features of this procedure were characterized by [...] Read more.
A green, convenient and tandem procedure for the efficient synthesis of highly substituted indeno[1,2-b]pyrrole and acenaphtho[1,2-b]pyrrole derivatives by domino three-component reaction of tryptamine/benzylamine, 1,3-dicarbonyl compounds and ninhydrin/ acenaphthenequinone is described. The significant features of this procedure were characterized by mild reaction conditions, high yields, operational simplicity and it being environmentally benign. Full article
(This article belongs to the Special Issue Multicomponent Reactions)
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6 pages, 1220 KiB  
Article
Multi-Gram Synthesis of Enantiopure 1,5-Disubstituted Tetrazoles Via Ugi-Azide 3-Component Reaction
by Pietro Capurro, Lisa Moni, Andrea Galatini, Christian Mang and Andrea Basso
Molecules 2018, 23(11), 2758; https://doi.org/10.3390/molecules23112758 - 25 Oct 2018
Cited by 12 | Viewed by 3483
Abstract
Tetrazoles have been widely studied for their biological properties. An efficient route for large-scale synthesis of 1,5-disubstituted tetrazoles (1,5-DTs) is presented. The strategy exploits a reductive approach to synthetize a cyclic chiral imine substrate which is then converted into the target product through [...] Read more.
Tetrazoles have been widely studied for their biological properties. An efficient route for large-scale synthesis of 1,5-disubstituted tetrazoles (1,5-DTs) is presented. The strategy exploits a reductive approach to synthetize a cyclic chiral imine substrate which is then converted into the target product through an Ugi-azide three-component reaction (UA-3CR). The final products are equipped with additional functionalities which can be further elaborated for the generation of combinatorial libraries of enantiopure heterocycles. Full article
(This article belongs to the Special Issue Multicomponent Reactions)
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9 pages, 974 KiB  
Article
Synthesis of Spirooxindole-O-Naphthoquinone-Tetrazolo[1,5-a]Pyrimidine Hybrids as Potential Anticancer Agents
by Liqiang Wu, Yunxia Liu and Yazhen Li
Molecules 2018, 23(9), 2330; https://doi.org/10.3390/molecules23092330 - 12 Sep 2018
Cited by 37 | Viewed by 3949 | Correction
Abstract
A series of novel spirooxindole-O-naphthoquinone-tetrazolo[1,5-a]pyrimidine hybrids were designed, synthesized and evaluated as potent antitumor agents. These hybrids exhibited relatively high cytotoxic activity against cancer cell line HepG2 (IC50 = 2.86–36.34 μM), while normal cell line LO2 was less [...] Read more.
A series of novel spirooxindole-O-naphthoquinone-tetrazolo[1,5-a]pyrimidine hybrids were designed, synthesized and evaluated as potent antitumor agents. These hybrids exhibited relatively high cytotoxic activity against cancer cell line HepG2 (IC50 = 2.86–36.34 μM), while normal cell line LO2 was less sensitive to these hybrids (IC50 = 36.37–248.39 μM). On the whole, among all the compounds tested, compound 4e, with a mean IC50 value of 2.86 μM, was the most active. The novel hybrids may find their pharmaceutical applications after further investigations. Full article
(This article belongs to the Special Issue Multicomponent Reactions)
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8 pages, 795 KiB  
Article
Synthesis of Novel 1,4-Naphthoquinones Possessing Indole Scaffolds Using In(OTf)3 in Solvent-Free Conditions
by Xiaojuan Yang and Liqiang Wu
Molecules 2018, 23(8), 1954; https://doi.org/10.3390/molecules23081954 - 6 Aug 2018
Cited by 6 | Viewed by 2918
Abstract
Novel 1,4-naphthoquinones possessing indole scaffolds were prepared by the reaction of 2-hydroxy-1,4-naphthoquinone-substituted salicylic aldehydes and indoles using In(OTf)3 as a catalyst. The method has the advantages of simple operation, mild reaction conditions, and friendly environment. Full article
(This article belongs to the Special Issue Multicomponent Reactions)
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Review

Jump to: Editorial, Research

18 pages, 17586 KiB  
Review
The Asymmetric A3(Aldehyde–Alkyne–Amine) Coupling: Highly Enantioselective Access to Propargylamines
by Jia-Nan Mo, Junqi Su and Jiannan Zhao
Molecules 2019, 24(7), 1216; https://doi.org/10.3390/molecules24071216 - 28 Mar 2019
Cited by 42 | Viewed by 7186
Abstract
The recent developments in asymmetric A3 (aldehyde–alkyne–amine) coupling has been summarized in this review. Several interesting modifications of the ligands enabled the highly enantioselective synthesis of chiral propargylamines, which are further used in the construction of nitrogen-containing chiral building blocks. Full article
(This article belongs to the Special Issue Multicomponent Reactions)
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