Article
Chemistry, Organic
Marine Pinaud, Leila Vaitilingom, Gayathiri Gnanalingam, Tania Xavier, Erwan Le Gall, Marc Presset
Summary: The use of N-alkyl imines in decarboxylative Mannich reaction with substituted malonic acids half oxyesters (SMAHOs) has been developed to afford a direct access to secondary beta(2,3)-aminoesters. The transformation occurs under very practical conditions (DABCO as a catalyst in bulk toluene and open to air) and can be performed with a broad range of each substrate in yields of 36 to 97 %. Importantly, the reaction was found to require the use of acidic additives in combination with the organocatalyst to limit the competitive olefination reaction.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Marine Pinaud, Emilie Plantiveau, Eric Huet, Erwan Le Gall, Marc Presset
Summary: Mannich-type reactions involving alkylzinc reagents have been developed using different strategies. We found that simple heating allows the addition of these organometallic species to sulfonyl imines, giving Mannich products in moderate to excellent yields (14 examples, 30-99%). Interestingly, N-alkyl imines can also be used as suitable partners after activation as an acyliminium by acetyl chloride (12 examples, 49-86%) or, more originally, by TMSCl (14 examples, 26-87%). These methods are complementary, providing both N-protected secondary or tertiary amines and N-unprotected secondary amines in good yields, with improved eco-compatibility and under simple conditions.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Dong-Ping Wu, Wei Ou, Pei-Qiang Huang
Summary: This study describes the catalytic reductive condensation reactions between tertiary amides and active methylene compounds, leading to multifunctionalized non-N-containing products. The reactions proceed through a sequential process involving iridium-catalyzed hydrosilylation of the amides followed by acid-mediated condensation with the active methylene compounds. This scalable method demonstrates a broad scope and remarkable chemoselectivity for the amide group in the presence of various sensitive or even more reactive functionalities such as ester, cyano, nitro, silyl dienol ether, and ketone.
Article
Chemistry, Organic
Nicole D. Bartolo, Krystyna M. Demkiw, Elizabeth M. Valentin, Chunhua T. Hu, Alya A. Arabi, K. A. Woerpel
Summary: The stereoselectivities of reactions of allylmagnesium reagents with chiral ketones cannot be easily explained by stereochemical models, as observed in competition experiments. The irreversibility of the complexation step prevents nucleophiles from accessing a wide range of possible encounter complexes, making analysis using available models difficult. Nevertheless, stereoselective additions of allylmagnesium reagents to ketones can still occur if the carbonyl group adopts a conformation blocking one face from the approach of the reagent.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Review
Chemistry, Organic
Xabier del Corte, Edorta Martinez de Marigorta, Francisco Palacios, Javier Vicario, Aitor Maestro
Summary: Chiral phosphoric acids (CPAs) are efficient organocatalysts that have been widely used for enantioselective additions to C=O and C=N bonds.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Ruirui Zhang, Xia Peng, Jiajing Tan
Summary: Aryne chemistry is a powerful synthetic technique that forms new bonds to aromatic rings. The recent resurgence of aryne-based multicomponent coupling strategies has led to the development of mild synthesis methods for arene derivatives. This review provides a comprehensive overview of the recent progress in constructing C(sp(2))-O bonds through aryne-induced multicomponent reactions, focusing on reaction design and mechanistic pathways.
SYNTHESIS-STUTTGART
(2022)
Article
Chemistry, Organic
Jinni Liu, Yongshuang Li, Na Liu, Nianyu Huang, Long Wang, Dongsheng Li
Summary: A mild, highly efficient, and simple reaction using a novel organic framework material Cu-COOH@MOF-6 as catalyst has been developed for facile synthesis of alpha-amino amides. The Cu-COOH@MOF-6 catalyst features a highly porous metal-organic framework with exposed carboxyl groups, providing acid active sites that explain its catalytic performance. The catalyst maintains its efficiency after multiple reuses and remains stable under reaction conditions, as confirmed by unchanged powder XRD image.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Multidisciplinary
Naoki Yasukawa, Shuichi Nakamura
Summary: Catalytic enantioselective synthesis methodologies have been actively explored and developed to access valuable compounds such as unnatural alpha-amino acids. Asymmetric addition to ketimine-type electrophiles has been recognized as a powerful strategy, although it was limited a few decades ago. This feature article comprehensively overviews the research field and highlights the significant progress made, focusing on the chiral catalyst system and transition state as key parameters for such reactions.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Victor V. Dotsenko, Alexander Bespalov, Arthur S. Vashurin, Nicolai A. Aksenov, Inna Aksenova, Elena A. Chigorina, Sergey G. Krivokolysko
Summary: In this study, trans-2-amino-4-aryl-5-benzoyl-4,5-dihydrothiophene-3-carbonitriles were prepared through two different reaction pathways, and the mechanism of the first reaction was investigated using high-level quantum chemical calculations. A new approach to constructing the thieno[2,3-d]pyrimidine core system was demonstrated by reacting the prepared dihydrothiophenes with HCHO and RNH2 under noncatalyzed Mannich conditions.
Article
Chemistry, Multidisciplinary
Gamze Elmas, Arzu Binici, Mehtap Yakut, Aytug Okumus, Zeynel Kilic, Bunyemin Cosut, Tuncer Hokelek, Nebahat Aytuna Cerci, Leyla Acik
Summary: This study synthesized a series of new inorganic-organic hybrid multiheterocyclic-spiro and ansa cyclotetraphosphazenes by reacting octachlorocyclotetraphosphazene with different substrates. The products were characterized using various techniques, and their structures and stereogenic properties were studied by single crystal X-ray analysis. These compounds exhibited potential cytotoxic activities against various cell lines.
NEW JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Organic
Hajime Kameo
Summary: Polyfunctional ligands containing Lewis acid moieties have shown great potential in transition metal catalysis. Z-type ligands can function as electrophilic catalysts by interacting with the metal center, and they also promote cross-coupling reactions. This article presents two examples of metal-ligand cooperation: Pd-borane cooperation and cross-coupling reactions of fluoro-silanes and -germanes. These examples demonstrate the versatility of Z-type ligands in bond activation and cross-coupling reactions.
JOURNAL OF SYNTHETIC ORGANIC CHEMISTRY JAPAN
(2022)
Article
Chemistry, Organic
Marlyn C. Ortiz Villamizar, Carlos E. Puerto Galvis, Vladimir V. Kouznetsov
Summary: Through visible light photocatalysis and transition metal catalysis, we found that iridium-based photocatalysis as well as copper ([CuBr(PPh3)(3)]) and silver (AgNO3) catalysis can easily achieve 1-alkynylated THIQs under mild, selective, and accessible reaction conditions. The copper(I)-based methodology provided the most robust and optimal reaction conditions for synthesizing a series of 18 1-alkynylated THIQs with high selectivity for endo-alkynylated products.
SYNTHESIS-STUTTGART
(2021)
Article
Chemistry, Organic
Angelica Penaranda Gomez, Carlos E. Puerto Galvis, Mario A. Macias, Cristian Ochoa-Puentes, Vladimir V. Kouznetsov
Summary: A novel tandem approach was developed for the efficient synthesis of substituted chromeno[4,3-b]quinolines under metal-catalyst-and photosensitizer-free reaction conditions. The method, based on an inexpensive I(2)/DMSO system, features mild conditions, high step-economy, and provides a new access to biologically important nitrogen- and oxygen-containing heterocyclic molecules.
SYNTHESIS-STUTTGART
(2022)
Editorial Material
Chemistry, Organic
Carlos E. Puerto Galvis, Vladimir V. Kouznetsov
Summary: Numbrino (TM), a nasal anesthetic solution based on cocaine hydrochloride, has been approved by the FDA for diagnostic procedures and surgery. The role of controlling agencies and legislation in producing countries in addressing the medicinal use of cocaine is being debated. Chemistry may play a crucial role in proposing alternative approaches.
CURRENT ORGANIC CHEMISTRY
(2022)
Review
Polymer Science
Vladimir V. Kouznetsov, Leonor Y. Vargas Mendez
Summary: The importance of replacing traditional thermosets and their monomers obtained from petrochemical processes with biobased thermosets prepared from biomass has led to significant developments in this area. The conversion of plant biomass, particularly natural phenols like eugenol, into useful polymeric materials is believed to have considerable environmental and economic value. Eugenol shows promise due to its sourcing, structure, and chemical properties, which can enhance the physical characteristics of thermosetting materials and reduce their toxic effects. This review focuses on the utilization of eugenol for the synthesis of biobased epoxy and its thermosetting resins, with detailed descriptions of synthetic methods and the outstanding physical characteristics of the formulated materials.
JOURNAL OF APPLIED POLYMER SCIENCE
(2022)
Article
Chemistry, Organic
Sandra M. Bonilla-Castaneda, Andres F. Villamizar-Mogotocoro, Vladimir V. Kouznetsov
Summary: In this study, a new derivative was synthesized from commercial starting reagents through a two-step procedure. The compound exhibited various important pharmacological properties.
Article
Chemistry, Organic
Duvan A. Rodriguez Enciso, Carlos E. Puerto E. Galvis, Vladimir V. V. Kouznetsov
Summary: In this study, a new green and efficient method was developed to synthesize potentially bioactive functionalized 7-chloro-4-phenoxyquinolines and benzazole-quinoline molecules. The method offers advantages such as high yields, use of microwave irradiation and green solvent, and short reaction times.
CURRENT ORGANIC SYNTHESIS
(2023)
Article
Medicine, Research & Experimental
Semer Maksoud, Adriana Mayora, Laura Colman, Felipe Sojo, Adriana A. Pimentel, Vladimir V. Kouznetsov, Diego R. Merchan-Arenas, Angel H. Romero, Francisco Arvelo, Juan Bautista De Sanctis, Gustavo Benaim
Summary: Tetrahydroquinoline derivatives JS-56 and JS-92 exhibit antitumor effects on MCF-7 breast cancer cells by increasing intracellular Ca2+ concentration, inhibiting SERCA activity, and inducing cell death.
INVESTIGACION CLINICA
(2022)
Article
Biochemistry & Molecular Biology
Marlyn C. Ortiz Villamizar, Carlos E. Puerto Galvis, Silvia A. Pedraza Rodriguez, Fedor Zubkov, Vladimir V. Kouznetsov
Summary: A rapid and efficient synthesis of novel pyrido[3,2,1-de]phenanthridin-6-ones is reported, and the toxicological profile of the prepared compounds is explored.
Article
Biochemistry & Molecular Biology
Kirill A. Vasilyev, Alexandra S. Antonova, Nikita S. Volchkov, Nikita A. Logvinenko, Eugeniya V. Nikitina, Mikhail S. Grigoriev, Anton P. Novikov, Vladimir V. Kouznetsov, Kirill B. Polyanskii, Fedor I. Zubkov
Summary: An efficient approach to synthesizing HG-type catalysts for olefin metathesis, which contain an N -> Ru bond in a six-membered chelate ring, was proposed. These ruthenium chelates can be easily prepared and in high yields through the interaction between 2-vinylbenzylamines and Ind II. The stability of the ruthenium complexes decreases dramatically with an increase in steric volume of substituents attached to the nitrogen atom and in the alpha-position of the benzylidene fragment.
Review
Biochemistry & Molecular Biology
Fedor I. Zubkov, Vladimir V. Kouznetsov
Summary: Regardless of their complexity, all metabolites have specific missions or functions in the organisms that biosynthesize them. This review focuses on acetophenone as a metabolite involved in multiple interactions with various microorganisms. It discusses the biological, allelochemical, and chemical properties of acetophenone, along with its biogenesis, chemical synthesis, and potential applications in life sciences, such as agrochemicals and drug research.
Article
Chemistry, Organic
Andres-Felipe Villamizar-Mogotocoro, Vladimir V. Kouznetsov
Summary: We report an efficient method for synthesizing a series of new N-biphenyl-cinnamamides/3-arylpropanamides through a three-step, clean, good-yielding, and environmentally-friendly microwave-assisted procedure. The compounds were fully characterized by FT-IR, 1H, and 13C NMR and are reported for the first time.
TETRAHEDRON LETTERS
(2023)
Article
Chemistry, Multidisciplinary
Silvia J. Becerra-Anaya, Diego Merchan R. Arenas, Vladimir V. Kouznetsov
Summary: We report a simple and efficient method for the synthesis of 4-methylcoumarins series, including Coumarin 120 (7-amino-4-methylcoumarin), from phenols (or naphthols) and ethyl acetoacetate in the presence of 3 mol% InCl3. Coumarins were obtained with good yields (52-92%) through Pechmann condensation, using a high-speed ball mill mixer at room temperature, under solvent-free conditions with short reaction times.
CHEMISTRY-SWITZERLAND
(2023)
Article
Chemistry, Multidisciplinary
Dayana Orosco, Gustavo A. Barraza, Carlos Puerto E. Galvis, Vladimir V. Kouznetsov, Carlos M. Melendez
Summary: A series of functionalized 2,4-diphenylquinoline derivatives were successfully synthesized and their role in prostate cancer was investigated. The results of molecular docking and molecular dynamics simulations demonstrated that several compounds showed strong inhibition activity against KDM4B protein, with high binding affinity and stability.
NEW JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Andres-Felipe Villamizar-Mogotocoro, Sandra-Milena Bonilla-Castaneda, Vladimir V. Kouznetsov
Summary: An ecofriendly and efficient method for the synthesis of new pharmacologically active 6-arylphenanthridines has been developed using inexpensive starting materials and consecutive reactions under microwave assistance and a catalytic system, resulting in moderate to excellent yields.
Review
Chemistry, Multidisciplinary
Vladimir V. Kouznetsov, Jose G. Hernandez
Summary: Chemical processes are often catalytic transformations, where the use of catalysts helps reduce reaction temperature, minimize waste, and improve reaction selectivity. Multicomponent reactions (MCRs) and catalysis tools are valuable principles in green chemistry. Among MCRs, the three-component Strecker reaction (S-3-CR) is a significant transformation for the synthesis of bifunctional building blocks. The use of nanostructured catalysts has become associated with green pathways in achieving sustainability.
