Matthieu Pélingre, Dindet Steve-Evanes Koffi Teki, Jamal El-Abid, Vincent Chagnault, José Kovensky & Véronique Bonnet·Organics·2021
Many preparations of maltooligosaccharides have been described in literature, essentially using enzymatic or biotechnological processes. These compounds, derived from starch, are well-known as prebiotic agents. The use of maltohexa-, hepta-, and octaoses as synthons in organic sy...
Mar Ríos Gutiérrez, Luis Domingo & Fatemeh Ghodsi·Organics·2021
The reactivity of a series of pairs of bent and linear three-atom-component (B-TACs and L-TACs) participating in [3 + 2] cycloaddition (32CA) reactions towards ethylene and electrophilic dicyanoethylene (DCE) have been studied within the Molecular Electron Density Theory. While t...
Daisuke Sato, Zhiyuan Wu, Hikaru Fujita & Jonathan Lindsey·Organics·2021
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...
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-cre...
Pieterjan Winant, Tomas Horsten, Shaiani Gil de Melo, Flavio Emery & Wim Dehaen·Organics·2021
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 pr...
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 att...
Didier Villemin, Bernard Moreau & Nathalie Bar·Organics·2021
Novel 2-amino bis(2-phosphonoacetic) acids were prepared by microwave irradiation of a mixture of amine, glyoxylic acid and phosphorous acid. The reaction takes place with various amines including primary and secondary amines and polyamines, but this reaction is more sensitive to...
A convenient synthetic approach to previously unknown NH-iminophosphonates bearing 2-, 3-, and 4-pyridyldifluoromethyl groups at the imine carbon atom was developed. The synthetic potential of these novel building blocks was demonstrated by their conversion into highly functional...
An experimental and theoretical study of the reactivity and mechanism of the non-catalyzed and catalyzed Povarov reaction for the preparation of a 4-ethoxy-2,3,4,4a-tetrahydro-2-phenylquinoline as a biological active quinoline derivative has been performed. The optimization of ex...
Oshrat Levy-Ontman, Eliraz Stamker, Vital Mor & Adi Wolfson·Organics·2021
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 re...
Experimentally, a reversal of chemoselectivity has been observed in catalyzed Diels–Alder reactions of α,β-unsaturated aldehydes (e.g., (2E)-but-2-enal) and ketones (e.g., 2-hexen-4-one) with cyclopentadiene. Indeed, using the triflimidic Brønsted acid Tf2NH as catalyst, the reac...
The regiochemistry of [3+2] cycloaddition (32CA) processes between benzonitrile N-oxide 1 and β-phosphorylated analogues of nitroethenes 2a–c has been studied using the Density Functional Theory (DFT) at the M062X/6-31+G(d) theory level. The obtained results of reactivity indices...
Wenhong Lin, Shea Meyer, Shawn Dormann & John Chisholm·Organics·2021
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 a...
Mohammed El Idrissi, Mohamed El Ghozlani, Asli Eşme, Mar Ríos Gutiérrez, Anas Ouled Aitouna, Mohammed Salah, Habib El Alaoui El Abdallaoui, Abdellah Zeroual, Noureddine Mazoir & Luis Domingo·Organics·2021
The regioselectvity and the mechanism of the (32CA) cycloadditions reactions of 1-bromo-4-vinylbenzene 1 and 1-chloro-4-vinylbenzene 2 with benzonitrile oxide 3 were investigated under the molecular electron density theory (MEDT) at the B3LYP/6-311++G(d,p) computational level. Ev...
New discoveries require a fundamental revision of the view on the mechanism of the 32CAreaction (according to the older nomenclature defined as 1,3-dipolar cycloaddition reactions). The view of the one-step, “concerted” mechanism of such processes developed in the 20-century is v...