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Organics, Volume 5, Issue 2 (June 2024) – 6 articles

Cover Story (view full-size image): Polyether amines are versatile compounds characterized by a flexible structure of polyoxypropylene and polyoxyethylene backbones with amine groups at each end. This study demonstrates the innovative use of polyether amine as a recyclable catalyst for the aerobic oxidation of thiophenols, leading to the synthesis of disulfides. In contrast to known methods for thiol oxidation, this polyether amine-based catalytic process eliminates the need for expensive stoichiometric oxidants and minimizes the formation of over-oxidized by-products. A remarkable yield of over 96% was achieved for all 16 test substrates, encompassing a diverse range of functional groups under catalytic aerobic oxidation conditions, using just 0.5% of polyether amine as the catalyst. View this paper

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49 pages, 7257 KiB

Open AccessReview

Architecture of Molecular Logic Gates: From Design to Application as Optical Detection Devices

by Gleiston G. Dias and Francielly T. Souto

Organics 2024, 5(2), 114-162; https://doi.org/10.3390/org5020008 - 6 Jun 2024

Cited by 2 | Viewed by 2152

Abstract

Three decades after A. P. de Silva’s seminal paper introduced the concept of logic gates at the molecular level, the field of molecular logic gates (MLGs) has witnessed significant advancements. MLGs are devices designed to perform logical operations, utilizing one or more physical or chemical stimulus signals (inputs) to generate an output response. Notably, MLGs have found diverse applications, with optical detection of analytes emerging as a notable evolution of traditional chemosensors. Organic synthesis methods are pivotal in crafting molecular architectures tailored as optical devices capable of analyte detection through logical functions. This review delves into the fundamental aspects and physical–chemical properties of MLGs, with a particular emphasis on synthetic strategies driving their design. Full article

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3 pages, 161 KiB

Open AccessEditorial

Special Issue “Progress in Synthesis and Applications of Phosphorus-Containing Compounds”

by Tomasz K. Olszewski

Organics 2024, 5(2), 111-113; https://doi.org/10.3390/org5020007 - 27 May 2024

Viewed by 858

Abstract

Organophosphorus compounds, due to their interesting physicochemical properties, have found wide applications in many important areas of the chemical industry, such as the synthesis of utility chemicals [...] Full article

(This article belongs to the Special Issue Progress in Synthesis and Applications of Phosphorus-Containing Compounds)

40 pages, 29528 KiB

Open AccessReview

How Much Potential Do Nucleoside Analogs Offer to Combat Human Corona Viruses?

by Włodzimierz Buchowicz and Mariola Koszytkowska-Stawińska

Organics 2024, 5(2), 71-110; https://doi.org/10.3390/org5020006 - 8 May 2024

Viewed by 1661

Abstract

Nucleoside analogs (NAs) have been extensively examined as plausible antiviral agents in recent years, in particular since the outbreak of the global pandemic of COVID-19 in 2019. In this review, the structures and antiviral properties of over 450 NAs are collected according to the type of virus, namely SARS-CoV, SARS-CoV-2, MERS-CoV, HCoV-OC43, HCoV-229E, and HCoV-NL63. The activity of the NAs against HCoV-related enzymes is also presented. Selected studies dealing with the mode of action of the NAs are discussed in detail. The repurposing of known NAs appears to be the most extensively investigated scientific approach towards efficacious anti-HCoV agents. The recently reported de novo-designed NAs seem to open up additional approaches to new drug candidates. Full article

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12 pages, 3310 KiB

Open AccessArticle

Innovative Application of Polyether Amine as a Recyclable Catalyst in Aerobic Thiophenol Oxidation

by Lingxia Chen, Junyu Li, Ke Ni, Xinshu Qin, Lijun Wang, Jiaman Hou, Chao Wang, Xuan Li, Minlong Wang and Jie An

Organics 2024, 5(2), 59-70; https://doi.org/10.3390/org5020005 - 26 Apr 2024

Cited by 1 | Viewed by 1207

Abstract

Polyether amines are versatile compounds characterized by a flexible structure, consisting of polyoxypropylene and polyoxyethylene as the backbone, with amine groups at each end. They have widespread applications in various industrial processes and daily life. Despite their versatility, the utilization of polyether amines as base catalysts is rare. In this study, one kind of three-arm polyether amine 1 was employed as an environmentally friendly, cost-effective catalyst for the aerobic oxidation of thiophenols, leading to the synthesis of disulfides. The oxidative coupling of thiols serves as a fundamental pathway for the production of disulfides, which are vital in both chemical and biological processes. In contrast to known methods for thiol oxidation, this polyether amine-based catalytic process eliminates the need for expensive stoichiometric oxidants and minimizes the formation of over-oxidized by-products. Using a mere 0.5 mol % of the polyether amine 1 as the catalyst, a remarkable > 96% yield was achieved for all 16 tested substrates, encompassing a diverse range of functional groups, under the catalytic aerobic oxidation conditions. Furthermore, it is noteworthy that over 90% of the polyether amine catalyst can be efficiently recovered for reuse without loss of activity, making this a sustainable and cost-effective catalytic approach. Full article

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13 pages, 3086 KiB

Open AccessArticle

Synthesis of Novel Trisubstituted Olefin-Type Probe Molecules Containing N-Heterocycles and Their Application in Detection of Malononitrile

by Zhao-Hua Chen, Shi-Wei Yu, Wen-Jin Xu, Miao-Xin Li, Yong Zeng, Si-Wei Deng, Jian-Yun Lin and Zhao-Yang Wang

Organics 2024, 5(2), 46-58; https://doi.org/10.3390/org5020004 - 2 Apr 2024

Cited by 4 | Viewed by 1281

Abstract

Recently, the construction of the trisubstituted olefin-type probe molecules has elicited the attention of many researchers. However, the synthesis of the trisubstituted olefin-type probes containing two N-heterocycles simultaneously has been rarely reported. In this study, starting from the inexpensive mucobromic acid 1 and N-heterocyclic compound 2, we first utilized a simple one-step reaction to synthesize a series of trisubstituted olefin-type compounds 3 simultaneously bearing with the structure of two N-heterocyclic rings in the absence of transition metal catalysts with a yield of 62–86%. The optimal reaction conditions were systematically explored, and the structure of the obtained compounds 3 were well characterized with ¹H NMR, ¹³C NMR, X-ray single-crystal and HR-MS. The preliminary observation showed that, in the presence of base, mucobromic acid 1 reacts as its ring-opening structure, and the successive nucleophilic substitution reaction and Michael addition reaction can generate the target product 3. Considering that the aldehyde group in the molecular structure of the trisubstituted olefin-type compounds 3 may react with malononitrile, we carried out some relevant investigations so as to realize the visual detection of malononitrile. Interestingly, among the products, compounds 3a–3c can be prepared in portable test strips through a simple process and used to achieve the naked-eye detection of malononitrile in environmental systems as designed. Full article

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14 pages, 4465 KiB

Open AccessArticle

Supramolecular Catalysis with Chiral Mono- and Bis-(Thio)Urea-Derivatives

by Veronica Iuliano, Paolo Della Sala, Carmen Talotta, Margherita De Rosa, Carmine Gaeta, Placido Neri and Annunziata Soriente

Organics 2024, 5(2), 32-45; https://doi.org/10.3390/org5020003 - 26 Mar 2024

Viewed by 955

Abstract

Chiral mono- and bis-(thio)urea supramolecular organocatalysts were studied in the enantioselective vinylogous addition reaction of 2-trimethylsilyloxyfuran (TMSOF) to carbonylic compounds; the corresponding chiral γ-hydroxymethyl-butenolides are obtained in good yields and with high enantiomeric excesses. The catalyst structure, as well as the reaction conditions, strongly influence the efficiency of the reaction. The conformational features of mono(thio)urea catalysts 2 and 3 and bis(thio)urea catalysts 7 and 8 were investigated by DFT calculations along with the structure of their complexes with benzaldehyde. Natural Bond Orbital (NBO) and Non-Covalent Interaction (NCI) calculations provided useful information concerning the activating H-bonding interactions in the complexes. Full article

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