Special Issue "Feature Papers in Organics"

A special issue of Organics (ISSN 2673-401X).

Deadline for manuscript submissions: 31 October 2021.

Special Issue Editors

Prof. Dr. Wim Dehaen
E-Mail Website
Guest Editor
Molecular Design and Synthesis, Department of Chemistry, KU Leuven, Leuven Chem&Tech, Celestijnenlaan 200F, B-3001 Leuven, Belgium
Interests: organic chemistry; heterocyclic chemistry; supramolecular chemistry
Special Issues, Collections and Topics in MDPI journals
Prof. Dr. Michal Szostak
E-Mail Website
Guest Editor
Department of Chemistry, Rutgers University, 73 Warren St, Newark, NJ 07102, USA
Interests: amide bonds; N-heterocyclic carbenes; C-N activation; C-H activation; C-O activation; lanthanides; cross-coupling; catalysis; reductions; reductive couplings; radical chemistry; synthetic methodology; natural products
Special Issues, Collections and Topics in MDPI journals
Prof. Dr. Huaping Xu
E-Mail Website
Guest Editor
Key Laboratory of Organic Optoelectronics and Molecular Engineering, Department of Chemistry, Tsinghua University, Beijing 100084, China
Interests: supramolecular chemistry; dynamic covalent bond; selenium; tellurium; self-assembly

Special Issue Information

Dear Colleagues,

We are glad to announce the Special Issue entitled "Feature Papers in Organics". It is open to receiving high-quality papers which will be published, free of charge, in Open Access form after peer review. We welcome the submission of manuscripts from Editorial Board Members and from outstanding scholars invited by the Academic Editors and the Editorial Office. We are flexible with the types of manuscript accepted, including original research articles, short communications, highlights of new developments, and insightful critical reviews. Detailed experimental procedures are required for research articles and communications.

As you see in the keywords list, sample research topics included in this Special Issue represent the whole journal. This is intended to open more chances for submissions related to organic chemistry around the world.

Prof. Dr. Wim Dehaen
Prof. Dr. Michal Szostak
Prof. Dr. Huaping Xu
Guest Editors

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. Organics is an international peer-reviewed open access quarterly 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 1000 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
  • Development of synthetic methodology
  • Theoretical organic chemistry
  • Physical organic chemistry
  • Supramolecular and macromolecular chemistry
  • Heterocyclic chemistry
  • Organocatalysis
  • Bioorganic chemistry
  • Organometallic chemistry
  • Functional organic materials

Published Papers (8 papers)

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Research

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Article
A Sustainable Improvement of ω-Bromoalkylphosphonates Synthesis to Access Novel KuQuinones
Organics 2021, 2(2), 107-117; https://0-doi-org.brum.beds.ac.uk/10.3390/org2020010 - 03 Jun 2021
Cited by 1 | Viewed by 794
Abstract
Owing to the attractiveness of organic phosphonic acids and esters in the pharmacological field and in the functionalization of conductive metal-oxides, the research of effective synthetic protocols is pivotal. Among the others, ω-bromoalkylphosphonates are gaining particular attention because they are useful building [...] Read more.
Owing to the attractiveness of organic phosphonic acids and esters in the pharmacological field and in the functionalization of conductive metal-oxides, the research of effective synthetic protocols is pivotal. Among the others, ω-bromoalkylphosphonates are gaining particular attention because they are useful building blocks for the tailored functionalization of complex organic molecules. Hence, in this work, the optimization of Michaelis–Arbuzov reaction conditions for ω-bromoalkylphosphonates has been performed, to improve process sustainability while maintaining good yields. Synthesized ω-bromoalkylphosphonates have been successfully adopted for the synthesis of new KuQuinone phosphonate esters and, by hydrolysis, phosphonic acid KuQuinone derivatives have been obtained for the first time. Considering the high affinity with metal-oxides, KuQuinones bearing phosphonic acid terminal groups are promising candidates for biomedical and photo(electro)chemical applications. Full article
(This article belongs to the Special Issue Feature Papers in Organics)
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Article
Pd-Based Polysaccharide Hydrogels as Heterogeneous Catalysts for Oxidation of Aromatic Alcohols
Organics 2021, 2(1), 50-56; https://0-doi-org.brum.beds.ac.uk/10.3390/org2010005 - 17 Mar 2021
Cited by 1 | Viewed by 6360
Abstract
Immobilization of Pd(OAc)2(TPPTS)2 in various renewable polysaccharides hydrogels, yielded heterogeneous catalysts that were successfully used, for the first time, in the aerobic oxidation of benzylic alcohol. The new catalysts were easily removed from the reaction mixture and recycled with some [...] Read more.
Immobilization of Pd(OAc)2(TPPTS)2 in various renewable polysaccharides hydrogels, yielded heterogeneous catalysts that were successfully used, for the first time, in the aerobic oxidation of benzylic alcohol. The new catalysts were easily removed from the reaction mixture and recycled with some loss of activity. Among all tested polysaccharides, iota-carrageenan was found to be the most suitable support, using calcium chloride as a gelation agent. Full article
(This article belongs to the Special Issue Feature Papers in Organics)
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Article
Esterifications with 2-(Trimethylsilyl)ethyl 2,2,2-Trichloroacetimidate
Organics 2021, 2(1), 17-25; https://0-doi-org.brum.beds.ac.uk/10.3390/org2010002 - 04 Feb 2021
Viewed by 872
Abstract
2-(Trimethylsilyl)ethyl 2,2,2-trichloroacetimidate is readily synthesized from 2-trimethylsilylethanol in high yield. This imidate is an effective reagent for the formation of 2-trimethylsilylethyl esters without the need for an exogenous promoter or catalyst, as the carboxylic acid substrate is acidic enough to promote ester formation [...] Read more.
2-(Trimethylsilyl)ethyl 2,2,2-trichloroacetimidate is readily synthesized from 2-trimethylsilylethanol in high yield. This imidate is an effective reagent for the formation of 2-trimethylsilylethyl esters without the need for an exogenous promoter or catalyst, as the carboxylic acid substrate is acidic enough to promote ester formation without an additive. A deuterium labeling study indicated that a β-silyl carbocation intermediate is involved in the transformation. Full article
(This article belongs to the Special Issue Feature Papers in Organics)
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Review

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Review
Synthesis of 1-Trifluorometylindanes and Close Structures: A Mini Review
Organics 2021, 2(4), 348-364; https://0-doi-org.brum.beds.ac.uk/10.3390/org2040019 - 08 Oct 2021
Viewed by 216
Abstract
This review describes methods for the synthesis of 1-trifluomethylindanes and close structures, which are still quite rare and scarcely available compounds. There are two main approaches to obtain 1-CF3-indanes. The first one is the construction of an indane system from CF [...] Read more.
This review describes methods for the synthesis of 1-trifluomethylindanes and close structures, which are still quite rare and scarcely available compounds. There are two main approaches to obtain 1-CF3-indanes. The first one is the construction of an indane system from CF3 precursors; the main methods are acid-mediated Friedel–Crafts cyclization, transition metal-catalyzed [3+2] annulation, and free-radical transformations. The second approach is the trifluoromethylation of a ready-made indane core by various CF3 sources, such as Ruppert–Prakash or Togni reagents. Many of these synthetic procedures possess high regio- and stereo-selectivity, allowing the preparation of unique 1-CF3-indane structures. In recent years, great attention has been paid to the synthesis of 1-CF3-indanes, due to the discovery of important biologically active properties for these compounds. Full article
(This article belongs to the Special Issue Feature Papers in Organics)
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Review
Recent Advances in the Synthesis of Piperazines: Focus on C–H Functionalization
Organics 2021, 2(4), 337-347; https://0-doi-org.brum.beds.ac.uk/10.3390/org2040018 - 08 Oct 2021
Viewed by 228
Abstract
Piperazine ranks as the third most common nitrogen heterocycle in drug discovery, and it is the key component of several blockbuster drugs, such as Imatinib (also marketed as Gleevec) or Sildenafil, sold as Viagra. Despite its wide use in medicinal chemistry, the structural [...] Read more.
Piperazine ranks as the third most common nitrogen heterocycle in drug discovery, and it is the key component of several blockbuster drugs, such as Imatinib (also marketed as Gleevec) or Sildenafil, sold as Viagra. Despite its wide use in medicinal chemistry, the structural diversity of piperazines is limited, with about 80% of piperazine-containing drugs containing substituents only at the nitrogen positions. Recently, major advances have been made in the C–H functionalization of the carbon atoms of the piperazine ring. Herein, we present an overview of the recent synthetic methods to afford functionalized piperazines with a focus on C–H functionalization. Full article
(This article belongs to the Special Issue Feature Papers in Organics)
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Review
Design, Synthesis, and Utility of Defined Molecular Scaffolds
Organics 2021, 2(3), 161-273; https://0-doi-org.brum.beds.ac.uk/10.3390/org2030013 - 11 Jul 2021
Cited by 1 | Viewed by 918
Abstract
A growing theme in chemistry is the joining of multiple organic molecular building blocks to create functional molecules. Diverse derivatizable structures—here termed “scaffolds” comprised of “hubs”—provide the foundation for systematic covalent organization of a rich variety of building blocks. This review encompasses 30 [...] Read more.
A growing theme in chemistry is the joining of multiple organic molecular building blocks to create functional molecules. Diverse derivatizable structures—here termed “scaffolds” comprised of “hubs”—provide the foundation for systematic covalent organization of a rich variety of building blocks. This review encompasses 30 tri- or tetra-armed molecular hubs (e.g., triazine, lysine, arenes, dyes) that are used directly or in combination to give linear, cyclic, or branched scaffolds. Each scaffold is categorized by graph theory into one of 31 trees to express the molecular connectivity and overall architecture. Rational chemistry with exacting numbers of derivatizable sites is emphasized. The incorporation of water-solubilization motifs, robust or self-immolative linkers, enzymatically cleavable groups and functional appendages affords immense (and often late-stage) diversification of the scaffolds. Altogether, 107 target molecules are reviewed along with 19 syntheses to illustrate the distinctive chemistries for creating and derivatizing scaffolds. The review covers the history of the field up through 2020, briefly touching on statistically derivatized carriers employed in immunology as counterpoints to the rationally assembled and derivatized scaffolds here, although most citations are from the past two decades. The scaffolds are used widely in fields ranging from pure chemistry to artificial photosynthesis and biomedical sciences. Full article
(This article belongs to the Special Issue Feature Papers in Organics)
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Review
Development of Efficient and Selective Processes for the Synthesis of Commercially Important Chlorinated Phenols
Organics 2021, 2(3), 142-160; https://0-doi-org.brum.beds.ac.uk/10.3390/org2030012 - 08 Jul 2021
Viewed by 560
Abstract
para-Selective processes for the chlorination of phenols using sulphuryl chloride in the presence of various sulphur-containing catalysts have been successfully developed. Several chlorinated phenols, especially those derived by para-chlorination of phenol, ortho-cresol, meta-cresol, and meta-xylenol, are of significant [...] Read more.
para-Selective processes for the chlorination of phenols using sulphuryl chloride in the presence of various sulphur-containing catalysts have been successfully developed. Several chlorinated phenols, especially those derived by para-chlorination of phenol, ortho-cresol, meta-cresol, and meta-xylenol, are of significant commercial importance, but chlorination reactions of such phenols are not always as regioselective as would be desirable. We, therefore, undertook the challenge of developing suitable catalysts that might promote greater regioselectivity under conditions that might still be applicable for the commercial manufacture of products on a large scale. In this review, we chart our progress in this endeavour from early studies involving inorganic solids as potential catalysts, through the use of simple dialkyl sulphides, which were effective but unsuitable for commercial application, and through a variety of other types of sulphur compounds, to the eventual identification of particular poly(alkylene sulphide)s as very useful catalysts. When used in conjunction with a Lewis acid such as aluminium or ferric chloride as an activator, and with sulphuryl chloride as the reagent, quantitative yields of chlorophenols can be obtained with very high regioselectivity in the presence of tiny amounts of the polymeric sulphides, usually in solvent-free conditions (unless the phenol starting material is solid at temperatures even above about 50 °C). Notably, poly(alkylene sulphide)s containing longer spacer groups are particularly para-selective in the chlorination of m-cresol and m-xylenol, while, ones with shorter spacers are particularly para-selective in the chlorination of phenol, 2-chlorophenol, and o-cresol. Such chlorination processes result in some of the highest para/ortho ratios reported for the chlorination of phenols. Full article
(This article belongs to the Special Issue Feature Papers in Organics)
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Review
A Review of the Synthetic Strategies toward Dihydropyrrolo[1,2-a]Pyrazinones
Organics 2021, 2(2), 118-141; https://0-doi-org.brum.beds.ac.uk/10.3390/org2020011 - 04 Jun 2021
Viewed by 768
Abstract
Dihydropyrrolo[1,2-a]pyrazinone rings are a class of heterocycles present in a wide range of bioactive natural products and analogues thereof. As a direct result of their bioactivity, the synthesis of this privileged class of compounds has been extensively studied. This review provides [...] Read more.
Dihydropyrrolo[1,2-a]pyrazinone rings are a class of heterocycles present in a wide range of bioactive natural products and analogues thereof. As a direct result of their bioactivity, the synthesis of this privileged class of compounds has been extensively studied. This review provides an overview of these synthetic pathways. The literature is covered up until 2020 and is organized according to the specific strategies used to construct the scaffold: fusing a pyrazinone to an existing pyrrole, employing a pyrazinone-first strategy, an array of multicomponent reactions and some miscellaneous reactions. Full article
(This article belongs to the Special Issue Feature Papers in Organics)
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Planned Papers

The below list represents only planned manuscripts. Some of these manuscripts have not been received by the Editorial Office yet. Papers submitted to MDPI journals are subject to peer-review.

Title: SYNTHESIS OF NOVEL PYRAZOLOPYRIDINES WITH AFFINITY FOR β-AMYLOID PLAQUES AND FIBRILS
Authors: Vidali, V.P 1,*; Georgia Nigianni 1,2; Aleksander Canko 1; Varvara Mavroidi 2; Dimitris Matiadis 2,*; Marina Sagnou 2
Affiliation: 1 NCSR "Demokritos", Institute of Nanoscience & Nanotechnology, Patr. Grigoriou & Neapoleos 27, Athens, 153 41, Greece 2 NCSR "Demokritos", Institute of Biosciences & Applications, Patr. Grigoriou & Neapoleos 27, Athens, 153 41, Greece
Abstract: Pyrazole-containing fused heterocyclic systems are ranked among the most versatile bioactive compounds, and a variety of procedures have been developed for their synthesis. In particular, pyrazolo[3,4-b]pyridines constitute a group of fused heterocyclic systems with outstanding chemical, biological and medicinal significance. More specifically, this privileged scaffold is the main structural component of clinically used drugs against Alzheimer’s disease. To this end, a small library of pyrazolo[3,4-b]pyridines was prepared by reacting the 1-phenyl-1H-pyrazol-5-amine with various α,β-unsaturated ketones in the presence of ZrCl4. The desired ketones were afforded from various aldehydes via a Claisen-Schmidt condensation reaction with acetone or via a Wittig reaction with 1-triphenylphosphoranylidene-2-propanone. The novel pyrazolopyridines were evaluated for their affinity for amyloid plaques by means of fluorescence microscopy fluorescence images of consecutive brain slices from autopsy confirmed AD patient. Among them, the highly fluorescent dimethylamine-bearing derivative was able to selectively stain the amyloid plaques. Moreover, the thioflavin T (ThT) fluorescence test that detects mature Aβ fibrils, revealed that the vanillin containing pyrazolopyridine interfered significantly with the rate of Aβ fibrilisation. Overall our results strongly support the high potential of the privileged pyrazolo[3,4-b]pyridine scaffold as an AD diagnostic or therapeutic agent.

Title: BORANILS: Versatile Multifunctional Organic Fluorophores for Innovative Applications
Authors: Julien Massue 1; Denis Jacquemin 2; Gilles Ulrich 1
Affiliation: 1 ICPEES, CNRS-UMR7515, Université de Strasbourg, France 2 CEISAM Lab-UMR 6230-CNRS & University of Nantes, 2 Rue de la Houssinière, 44322 Nantes, France
Abstract: Multifunctional stimuli-responsive fluorophores with bright, environment-sensitive fluorescence emissions have fueled intense research for their innovative applications in the field of biotechnologies, optoelectronics and materials. A strong structural diversity is observed among smart molecular materials, which has been enriched over the years with a growing responsiveness to stimuli. Boron dipyrromethene (BODIPY) dyes have long been the flagship of boron complexes due to their outstanding properties until a decade ago when analogues based on N^O, N^N or N^C π-conjugated chelates have emerged. The finality of developing alternates borate dyes was to compensate for BODIPYs’ lack of solid-state fluorescence and weak Stokes shifts while keeping their excellent optical properties in solution. Among them, the borate complexes based on an aniline-imine or salicylaldimine ligand, called by the acronym BORANILS appear as ones of the most promising, owing to their facile scalable synthesis and fine-tunable dual-state emission properties. Over the years, BORANIL dyes have proven to be good alternatives to BODIPY dyes and have been successfully applied in diverse but innovative applications such as aggregation-induced emission, room-temperature phosphorescence, mecanochemistry, bioimaging, bioconjugation and detection of biosubstrates or pollutants. Meanwhile, ab initio calculations have rationalized experimental results and provided insightful feedback for future designs. This review article aims at providing a concise but complete overview of the chemistry around the BORANIL core with the subsequent applications of the functionalized dyes. Theoretical aspects will also be discussed.

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