Article
Multidisciplinary Sciences
Bing-Bing Sun, Kun Liu, Quan Gao, Wei Fang, Shuang Lu, Chun-Ru Wang, Chuan-Zhi Yao, Hai-Qun Cao, Jie Yu
Summary: This article reports on a strategy that enables enantioselective Ugi four-component and Ugi-azide reactions using anionic stereogenic-at-cobalt(III) complexes as catalysts. By controlling the generation and trapping of key nitrilium intermediates, highly enantioselective alpha-acylamino amides and alpha-aminotetrazoles can be obtained.
NATURE COMMUNICATIONS
(2022)
Article
Biochemistry & Molecular Biology
Hung M. Nguyen, Nikita E. Golantsov, Alexandra S. Golubenkova, Victor B. Rybakov, Leonid G. Voskressensky
Summary: A multicomponent reaction involving isocyanides, aryl(indol-3-yl)methylium salts, and amines has been discovered, leading to the efficient synthesis of a series of aryl(indol-3-yl)acetimidamides. In some cases, the reaction proceeds with cyclization to form specific derivatives like 3,5-dihydro-4H-imidazol-4-one.
Article
Chemistry, Organic
Louis G. Mueller, Allen Chao, Embarek Alwedi, Maanasa Natrajan, Fraser F. Fleming
Summary: This passage describes a rapid method for assembling oxazoles, using Asmic and esters to synthesize oxazoles with an anisylsulfanyl substituent. The method can also be used to obtain compounds with different substituents, and has been applied in the synthesis of the bioactive streptochlorin.
Review
Chemistry, Organic
Vipin K. Maikhuri, Vineet Verma, Ankita Chaudhary, Divya Mathur, Rajesh Kumar, Ashok K. Prasad
Summary: Multicomponent reactions (MCRs) are a strategic chemical transformation involving three or more reactants in one pot to produce a functionalized final product. This method is ideal for achieving high complexity, diversity, yields, atom efficiency, and faster reaction times. Sugars, as naturally occurring compounds, have various hydroxy groups and defined stereochemistry, making them attractive for drug discovery. However, their potential in MCRs has only recently been realized. This article presents recent advances in the synthesis of sugar-derived heterocycles using MCRs, aiming to encourage the application of this powerful chemistry in generating novel glycoconjugate challenges.
SYNTHESIS-STUTTGART
(2023)
Article
Chemistry, Organic
Alexandre Quelhas, Houda Gazzeh, Thierry Roisnel, Yann Trolez, Jean-Claude Guillemin
Summary: Kinetically unstable vinyl, allenyl and propargyl isocyanides react faster in Passerini and Ugi reactions than they decompose, leading to functionalized amides that can be further used in reactions involving unsaturated substituents.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Biochemistry & Molecular Biology
Marco Manenti, Simone Gusmini, Leonardo Lo Presti, Giorgio Molteni, Alessandra Silvani
Summary: Various boron-containing isocyanides were efficiently synthesized from enantiopure beta-substituted beta-amino boronic acid pinacol esters. They were used in isocyanide-based multicomponent reactions to synthesize boron-containing peptidomimetics and heteroatom-rich small molecules.
MOLECULAR DIVERSITY
(2023)
Review
Chemistry, Multidisciplinary
Camilla Russo, Francesca Brunelli, Gian Cesare Tron, Mariateresa Giustiniano
Summary: Isocyanide-based multicomponent reactions have a long history and recent advances in visible light photocatalysis have led to new and green approaches. The application of visible light photocatalytic conditions to multicomponent processes has resulted in significant advancements, including radical-polar crossover pathways, photoinduced and self-catalyzed transformations, and reactions involving the generation of imidoyl radical species. This literature analysis provides an overview of the potential and challenges of exploiting isocyanides in visible light photocatalytic multicomponent reactions.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Pedro Brandao, Carolina S. Marques, Elisabete P. Carreiro, M. Pineiro, Anthony J. Burke
Summary: Multicomponent reactions (MCRs) are a valuable tool in diversity-oriented synthesis, gaining relevance in the fields of organic and medicinal chemistry. Isatin, with its unique reactivity, can undergo different MCRs to afford various interesting scaffolds, including oxindole-derivatives and heterocyclic compounds resulting from ring-opening reactions. New methodologies have been developed for the application of this easily available starting material in MCRs in recent years.
Article
Chemistry, Multidisciplinary
D. Basavaraja, M. S. Ajay Krishna, Jagadeesh Krishnan, C. S. Athira, R. R. Amrutha, Eringathodi Suresh, Sasidhar B. Somappa
Summary: The research achieved base assisted divergent reactivity of isatins and allenoates, leading to diastereoselective spirofuran oxindoles and gamma-functionalized allenoates. This method offers access to biologically relevant functionalized oxindole scaffolds with excellent substrate scope under mild reaction conditions.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Organic
Daniel S. Verdoorn, Prabhat Ranjan, Tim de Reuver, Elwin Janssen, Christophe M. L. Vande Velde, Jordy M. Saya, Bert U. W. Maes, Romano V. A. Orru
Summary: A cobalt-(II) mediated three-component synthesis of 5-substituted-N-sulfonyl-1,3,4-oxadiazol-2-(3H)-imines using sulfonyl azides, N-isocyanimino-triphenyl-phosphorane(NIITP), and carboxylic acids has been developed. The reaction proceeds through a nitrene transfer to NIITP, followed by addition of the carboxylic acid to the in situ formed carbodiimide and subsequent intramolecular aza-Wittig reaction. The selectivity towards the two products is determined by the steric constraints of carboxylic acid and the stoichiometry of the employed cobalt salt.
Article
Chemistry, Organic
Elfie S. Cavalli, Thomas Mies, Henry S. Rzepa, Andrew J. P. White, Philip J. Parsons, Anthony G. M. Barrett
Summary: An efficient two-step procedure for synthesizing pyrimidine nucleosides is described. Firstly, a series of glycosyl 5-(aminomethylene)-1,3-dioxane-4,6-dione derivatives were prepared, followed by transacylation reaction to obtain uridine-5-carboxylic acid derivatives and related nucleosides.
Review
Chemistry, Organic
Adrian Lavios, Amparo Sanz-Marco, Carlos Vila, Gonzalo Blay, Jose R. Pedro
Summary: The spirocyclic motif is widely found in natural products, chiral ligands, and pharmacologically active compounds. The formal [3+2] cycloaddition reaction of isothiocyanates or isocyanides with cyclic compounds has been developed for the enantioselective synthesis of aza-spirocyclic compounds, with organocatalysis playing a key role in these reactions. The synthesis of spirooxindoles using this methodology has received particular attention, highlighting the importance of the structure of the dipolarophiles and the isothiocyanate and isocyanide dipoles.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Biochemistry & Molecular Biology
Reagan L. Mohlala, Elena Mabel Coyanis, Muhammad Q. Fish, Manuel A. Fernandes, Moira L. Bode
Summary: A facile and efficient one-pot three-component reaction method for the synthesis of thiazine-dicarboxylates is reported, with good product yields. The reactivity of dialkyl acetylenedicarboxylates was demonstrated in both the thiazine-dicarboxylates synthesis and the synthesis of thiazole-pyrimidines, where a more efficient three-component reaction was achieved.
Review
Chemistry, Organic
Shrikant G. Pharande
Summary: This review summarizes strategies for the synthesis of alpha-, beta-, gamma-, delta- and epsilon-lactams using isocyanide-based multicomponent reactions (IMCRs) or IMCRs/post-transformation reactions reported in the literature between 2000 and 2020. Lactams are important heterocycles found in a wide range of bioactive molecules, natural products and drugs, leading to significant efforts in developing efficient synthesis methods. Despite their versatility in various fields of chemistry, there has been no dedicated review on IMCRs concerning lactam synthesis, highlighting the importance of this review.
SYNTHESIS-STUTTGART
(2021)
Article
Chemistry, Physical
Bruno Hessel Silva, Claudia Zlotea, Gavin Vaughan, Yannick Champion, Walter Jose Botta, Guilherme Zepon
Summary: Ti-V-Nb-Cr alloys were studied for their hydrogen storage properties using laboratory and synchrotron X-ray diffraction, Pair Distribution Function (PDF) analyses, Transmission Electron Microscopy (TEM), and thermo-desorption analyses (TDS). The results revealed a multi-step hydrogenation process in the alloy, which can be described by models with random atomic distribution. This research is of great significance for developing efficient hydrogen storage materials.
JOURNAL OF ALLOYS AND COMPOUNDS
(2022)
