Review
Chemistry, Multidisciplinary
Jia-Yin Wang, Wen-Juan Hao, Shu-Jiang Tu, Bo Jiang
Summary: This article provides a comprehensive overview of the transformations of yne-allenes, discussing their general and specific reactivities, presenting and commenting on their mechanisms and applications.
CHINESE JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Andrew Whyte, Jonathan Bajohr, Ramon Arora, Alexa Torelli, Mark Lautens
Summary: An enantioselective consecutive cyclization/coupling process catalyzed by palladium was reported in this study. The stereoinduction was achieved through an enantioselective carbopalladation, leading to the generation of an intermediate that promotes a nucleopalladation step. This dual cyclization sequence was compatible with various nucleophiles and aryl iodides, producing numerous bisheterocycles in good yields and high regio- and enantioselectivities.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Qingsong Deng, Aimin Yu, Lei Zhang, Xiangtai Meng
Summary: A stereospecific three-component domino reaction was revealed under catalyst-free conditions, leading to the synthesis of a wide range of benzothiophene-fused polycycles and eight-membered N-heterocycles. The control over product formation was achieved by regulating the stereoconfiguration of cyclohexane-1,2-diamines. The detailed mechanism and origin of the chemoselectivity were explored using density functional calculations, revealing the influence of intramolecular attractions and steric effects on the observed chemoselectivity.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Jacob C. Hood, Yannick Tshikaya, Aaren R. Manz, Marcus C. LaPorte, Douglas A. Klumpp
Summary: In this study, a series of conjugate addition reactions were successfully performed using vinyl-substituted N-heterocycles in acid-catalyzed conversions, resulting in the formation of pyridyl and related heterocyclic products. The nucleophiles used in these reactions include 1,3-dicarbonyl compounds, cyano esters, cyano sulfone, and malonylnitrile, while the Michael accepting groups include vinyl-substituted pyridines, quinoline, and pyrazine. Double conjugate addition reactions were also achieved using 2,6-divinylpyridine and related systems.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Patrick M. McCosker, Nicholas M. Butler, Alireza Shakoori, Michel K. Volland, Matthew J. Perry, Jesse W. Mullen, Anthony C. Willis, Timothy Clark, John B. Bremner, Dirk M. Guldi, Paul A. Keller
Summary: In this study, structurally diverse heterocycles were synthesized via cascade reactions of indigo with propargylic electrophiles, enabling chemical space exploration. It was found that the unsaturated propargyl moiety can act as an electrophile when aromatic terminal substitutions are made, competing with leaving group substitution to produce new outcomes. The products from these reactions were investigated for their absorption and fluorescence properties, revealing polarity dependent excited state relaxation pathways and highlighting these reactions as a rapid means to access diverse functional materials.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Organic
He Zhang, Linjuan Jiang, Mei Yang, Yuanhong Liu
Summary: A general and practical route for silylation of propargyl carbonates with silylboranes catalyzed by copper has been developed. Various propargyl carbonates with different substitution patterns are compatible with this catalytic system, allowing for the synthesis of diverse silylallenes efficiently and with functional group compatibility.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
Ouldouz Ghashghaei, Marina Pedrola, Francesca Seghetti, Victor V. Martin, Ricardo Zavarce, Michal Babiak, Jiri Novacek, Frederick Hartung, Katharina M. Rolfes, Thomas Haarmann-Stemmann, Rodolfo Lavilla
Summary: The participation of reactants in polarity inversion allows the continuation of productive domino processes in multicomponent reactions, leading to the discovery of novel reaction pathways and various polyheterocyclic scaffolds.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Applied
Sandor Balazs Kiraly, Laszlo Toth, Tibor Kovacs, Attila Benyei, Erika Lisztes, Balazs Istvan Toth, Tamas Biro, Attila Kiss-Szikszai, Katalin E. E. Kover, Attila Mandi, Tibor Kurtan
Summary: Four series of chiral condensed heterocycles, representing four novel skeletons and exhibiting antiproliferative activity, were synthesized through Domino Knoevenagel-cyclization reactions of 2H-chromene and chroman derivatives containing o-formylaryl amine or ether side-chain. The cyclization occurred through four different mechanisms: a concerted intramolecular hetero Diels-Alder reaction (IMHDA), a stepwise polar [2+2] cycloaddition, a [1,5]-hydride shift-6-endo cyclization, or a multi-step nitro hetero Diels-Alder-ring-opening-Cadogan-type cyclization sequence. The latter reaction provided a novel route to hydroxyindoles through an inverse Cadogan-type cyclization, where the nitro group is deoxygenated by a nitro IMHDA-ring-opening sequence. The cyclization mechanisms and stereoselectivity were studied using DFT calculations, which allowed for proposing a mechanism for the multi-step cyclization to hydroxyindoles and explaining the observed diastereoselectivity.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Physical
Rohit Kumar Maurya, Swadhapriya Bhukta, Keshav Kishor, Rana Chatterjee, Amarender Goud Burra, Mahender Khatravath, Rambabu Dandela
Summary: Boron-containing organometallic compounds have always intrigued organic chemists due to their wide application in carbon-carbon bond formation reactions. This review focuses on the arylative cyclization reactions using boronic acids as substrates under different transition metals, for the synthesis of densely functionalized heterocycles and bioactive scaffolds. The study highlights the growing interest in the field and provides an overview of recent developments.
JOURNAL OF MOLECULAR STRUCTURE
(2023)
Article
Biochemistry & Molecular Biology
Martina Palomba, Italo Franco Coelho Dias, Michelangelo Cocchioni, Francesca Marini, Claudio Santi, Luana Bagnoli
Summary: A new protocol for the synthesis of N-vinyl azoles using vinyl selenones and azoles in the presence of potassium hydroxide was developed. This reaction proceeded under mild and transition metal-free conditions through an addition/elimination cascade process. Both aromatic and aliphatic vinyl selenones and various mono-, bi- and tri-cyclic azoles can be tolerated and give terminal N-vinyl azoles in moderate to high yields. A plausible mechanism is also proposed.
Article
Chemistry, Organic
Peter Langer
Summary: The domino reactions of heterocyclic enamines with chromone derivatives lead to the synthesis of a variety of annulated heterocyclic ring systems, with the reaction pathway depending on the substituent at position 3 of the chromone. Functional groups at the carbonyl group of the chromone at position 3 allow for further synthetic transformations, including additional ring closures.
Article
Chemistry, Multidisciplinary
Olaya Bernardo, Silvia Gonzalez-Pelayo, Israel Fernandez, Luis A. Lopez
Summary: The gold-catalyzed reaction of propargyl esters with alkynylsilanes produces vinylallene derivatives through consecutive [1,2]-acyloxy/[1,2]-silyl rearrangements. This transformation features good yields, full atom-economy, a broad substrate scope, easy scale-up, and low catalyst loadings. The reaction mechanism involves the generation of a gold vinylcarbene intermediate and a type II-Dyotropic rearrangement involving the silyl group and the metal fragment.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Review
Biochemistry & Molecular Biology
Martina Palomba, Italo Franco Coelho Dias, Ornelio Rosati, Francesca Marini
Summary: Vinyl selenones have been rediscovered as useful building blocks for various synthetic transformations, including multiple-bond-forming reactions, one-pot synthesis, enantioselective construction, and total synthesis of natural products.
Review
Chemistry, Organic
Deeksha, Ritesh Singh
Summary: Aza-oxyallyl cations have diverse reactivity profiles for constructing N-scaffolds of biological interest and recent studies have reported new variations in their reactivity, making them versatile tools for organic synthesis.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Applied
Rayhane Hammami, Pascale Maldivi, Christian Philouze, Sebastien Carret, Benjamin Darses, Soufiane Touil, Jean-Francois Poisson
Summary: A variety of 4-phosphinylpyrrolidin-3-ones were synthesized via a [3+2] cycloaddition reaction between aryl aldonitrones and phosphinylallenes. The products were obtained as unique 4,5-trans diastereomers in yields ranging from 47% to 80% for 23 examples. Chiral racemic allenes exhibited a moderate 2:1 to 4:1 2,5-diastereoselectivity. Under the reaction conditions, the cycloadducts undergo a rearrangement to selectively afford the corresponding pyrrolidin-3-ones. DFT calculations provided insights into the mechanism involving the homolytic cleavage of the N-O bond of the cycloadduct.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
David Tejedor, Samuel Delgado-Hernandez, Raquel Diana-Rivero, Abian Diaz-Diaz, Fernando Garcia-Tellado
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2019)
Article
Chemistry, Multidisciplinary
David Tejedor, Samuel Delgado-Hernandez, Lucia Colella, Fernando Garcia-Tellado
CHEMISTRY-A EUROPEAN JOURNAL
(2019)
Article
Biochemistry & Molecular Biology
David Tejedor, Raquel Diana-Rivero, Fernando Garcia-Tellado
Article
Chemistry, Organic
Raquel Diana-Rivero, Beate Halsvik, Fernando Garcia Tellado, David Tejedor
Summary: A simple and metal-free domino methodology was used to synthesize various 2-aminopyrroles from alkynyl vinyl hydrazides, involving a novel rearrangement and cyclization reaction. This approach allowed the preparation of 2-amino-pyrroles with diverse substituents.
Article
Biochemistry & Molecular Biology
Samuel Delgado-Hernandez, Fernando Garcia-Tellado, David Tejedor
Summary: A novel organocatalytic multicomponent cyanovinylation reaction has been developed for the synthesis of conjugated cyanomethyl vinyl ethers, delivering excellent yields and predominance of the E-isomer. The reaction shows high tolerance to the structure and composition of aldehydes, and features instrumentally simple, cost-effective, environmentally friendly, and sustainable benefits.
Article
Chemistry, Medicinal
Carlos Bethencourt-Estrella, Samuel Delgado-Hernandez, Atteneri Lopez-Arencibia, Desiree San Nicolas-Hernandez, Ines Sifaoui, David Tejedor, Fernando Garcia-Tellado, Jacob Lorenzo-Morales, Jose Pinero
Summary: Chagas disease, caused by the protozoan parasite Trypanosoma cruzi, is a neglected infection that leads to over 7000 deaths annually, with limited therapy options available. A study has shown that novel acrylonitriles have potential as new trypanocidal agents for the treatment of Chagas disease.
Article
Parasitology
Aitor Rizo-Liendo, Inigo Arberas-Jimenez, Ines Sifaoui, Dimitra Gkolfi, Yiset Santana, Leandro Cotos, David Tejedor, Fernando Garcia-Tellado, Jose E. Pinero, Jacob Lorenzo-Morales
Summary: The study evaluated the activity of 14 novel isobenzofuranones against the pathogenic amoeba Naegleria fowleri, with some compounds showing the ability to eliminate trophozoites and induce programmed cell death. These tested compounds could potentially serve as therapeutic candidates for the treatment of Primary Amoebic Encephalitis.
INTERNATIONAL JOURNAL FOR PARASITOLOGY-DRUGS AND DRUG RESISTANCE
(2021)
Article
Medicine, Research & Experimental
Ruben L. Rodriguez-Exposito, Maria Reyes-Batlle, Ines Sifaoui, David Tejedor, Fernando Garcia-Tellado, Jose E. Pinero, Jacob Lorenzo-Morales
Summary: This study assessed the IC50 of isobenzofuranone derivatives against Acanthamoeba strains and identified two active derivatives with low IC50. Additionally, the study showed that both compounds triggered programmed cell death in Acanthamoeba strains.
BIOMEDICINE & PHARMACOTHERAPY
(2022)
Article
Biochemistry & Molecular Biology
Carlos J. Bethencourt-Estrella, Samuel Delgado-Hernandez, Atteneri Lopez-Arencibia, Desiree San Nicolas-Hernandez, David Tejedor, Fernando Garcia-Tellado, Jacob Lorenzo-Morales, Jose E. Pinero
Summary: Leishmaniasis is one of the most important tropical diseases, with approximately one million new cases each year. Current treatments are not fully effective and are toxic, so there is a need to develop new therapies that are more effective and less toxic. This study found that certain acrylonitrile derivatives have good selectivity in killing Leishmania parasites and induce programmed cell death.
BIOORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Tanausu Santos, Yaiza Perez-Perez, David S. Rivero, Raquel Diana-Rivero, Fernando Garcia-Tellado, David Tejedor, Romen Carrillo
Summary: Dynamic Covalent Chemistry (DCvC) plays an increasingly important role in supramolecular chemistry and materials science. In this study, we demonstrate the dynamic nature of the exchange between phenols and vinyl ethers. The fast exchange at room temperature and under mild conditions has been observed. The equilibrium constants and electronic effects of phenol substituents have been calculated. This novel incorporation into the DCvC toolbox holds great potential and has been successfully applied in the synthesis of a responsive molecular cage.
Article
Biochemistry & Molecular Biology
Javier Chao-Pellicer, Inigo Arberas-Jimenez, Samuel Delgado-Hernandez, Ines Sifaoui, David Tejedor, Fernando Garcia-Tellado, Jose E. Pinero, Jacob Lorenzo-Morales
Summary: This article discusses the research on primary amoebic meningoencephalitis (PAM) caused by the pathogenic amoeba Naegleria fowleri, as well as the treatment methods. The study found that QOET-51, QOET-59, QOET-64, QOET-67, QOET-72, QOET-77, and QOET-79 among the 46 synthesized compounds were the most effective molecules. Additionally, the study investigated the mechanism of action of these compounds.
ACS CHEMICAL NEUROSCIENCE
(2023)
Article
Parasitology
Carlos J. Bethencourt-Estrella, Samuel Delgado-Hernandez, Atteneri Lopez-Arencibia, Desiree San Nicolas-Hernandez, David Tejedor, Fernando Garcia-Tellado, Jacob Lorenzo-Morales, Jose E. Pinero
Summary: Chagas disease is a serious illness that can cause megacolon, heart disease, and even death. Current therapies for this disease are outdated and have significant side effects. Therefore, there is a need to search for new compounds that are safer, less toxic, and more effective against the parasite. This study investigated the antichagasic activity of 46 novel cyanomethyl vinyl ether derivatives and identified four compounds that showed selective activity and triggered programmed cell death in the parasites, making them potential candidates for future Chagas disease therapeutics.
INTERNATIONAL JOURNAL FOR PARASITOLOGY-DRUGS AND DRUG RESISTANCE
(2023)
Article
Chemistry, Multidisciplinary
David Tejedor, Samuel Delgado-Hernandez, Blanca Santamaria-Pelaez, Fernando Garcia-Tellado
CHEMICAL COMMUNICATIONS
(2020)
