Article
Chemistry, Organic
Nadia Sadou, Naouel Boufroua, Sophie Poulain-Martini, Elisabet Dunach, Samia Achouche-Bouzroura
Summary: A novel thiazolidinone derivative was synthesized via a three-component reaction, involving thiosemicarbazide, maleimide, and Meldrum's acid. The reaction conditions were optimized, and the best results were obtained with a specific ratio of raw materials and solvent, leading to high product yields and reduced reaction time.
SYNTHETIC COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Boris Lichitsky, Valeriya G. Melekhina, Andrey N. Komogortsev, Vasily A. Migulin, Yulia Nelyubina, Artem N. Fakhrutdinov, Elena D. Daeva, Arkady A. Dudinov
Summary: An efficient one-pot method was developed for the synthesis of previously unknown furanoflavone derivatives, based on a telescoped multicomponent reaction. The synthesis features regiospecific formation of a distinctive core structure. The advantages include mild conditions, atom economy, and easy workup procedure, avoiding the need for chromatographic purifications.
Article
Chemistry, Organic
Andrey N. Komogortsev, Boris V. Lichitsky, Valeriya G. Melekhina
Summary: A one-pot approach was developed for the synthesis of substituted colchicine derivatives based on the telescoped multicomponent reaction of colchiceine, arylglyoxals, and Meldrum's acid. The regiospecific formation of a distinctive moiety is a key feature of this method. Advantages include the use of readily accessible starting materials, process simplicity, and easy isolation of the target products.
TETRAHEDRON LETTERS
(2021)
Article
Chemistry, Multidisciplinary
Stephane Wittmann, Thomas Martzel, Cong Thanh Pham Truong, Martial Toffano, Sylvain Oudeyer, Regis Guillot, Chloee Bournaud, Vincent Gandon, Jean-Francois Briere, Giang Vo-Thanh
Summary: Through Bronsted base organocatalysis, ketone-derived alkylidene Meldrum's acids react with dihydro-2,3-furandione in a formal (4+2) cycloaddition reaction, yielding 3,6-dihydropyran-2-ones with up to 98% ee. This reaction can be extended to other activated ketones, making alkylidene Meldrum's acids a novel C4-synthon in the vinylogous series.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Review
Chemistry, Organic
Felix Brosge, Pardeep Singh, Fredrik Almqvist, Carsten Bolm
Summary: Meldrum's acid is a molecule with exceptional chemical properties, characterized by its low pK(a) value in water and reactivity in electrophilic and nucleophilic substitution reactions. At elevated temperatures, it undergoes distinctive decomposition pathways that can be used in cycloaddition and acylation reactions. Recent advances in utilizing Meldrum's acid derivatives in synthesis aim to further stimulate research towards innovative applications of this molecule.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Polymer Science
Zhang-Jun Fan, Ying-Ling Liu
Summary: Mainchain-type polybenzoxazines (PBz) are self-crosslinkable polymers possessing high flexibility of molecular designs and property adjustments. In this study, PBz was functionalized with amide groups and Meldrum's acid moieties to enhance hydrogen bonding interaction and additional covalent crosslinks. The resulting crosslinked PBz exhibited film formability, flexibility, and attractive thermal properties, including high thermal stability, char yield, storage modulus, and tensile strength, surpassing previously reported data for crosslinked polybenzoxazine films.
Article
Chemistry, Inorganic & Nuclear
Nur Iffah Fitri Idelfitri, Nur Nadia Dzulkifli, Nur Ain Nabilah Ash'ari, Suhaila Sapari, Fazira Ilyana Abdul Razak, Noor Hidayah Pungot
Summary: The synthesis and characterization of Meldrum's acid thiosemicarbazone derivative, 4NMATSC, was successfully carried out. The compound was verified to be an effective corrosion inhibitor for mild steel in hydrochloric acid.
INORGANIC CHEMISTRY COMMUNICATIONS
(2023)
Article
Chemistry, Applied
Julien Annibaletto, Thomas Martzel, Vincent Levacher, Sylvain Oudeyer, Jean-Francois Briere
Summary: The strategy reported involves a multicomponent catalytic enantioselective synthesis of beta-substituted isoxazolidin-5-ones via a KMC process promoted by a suitable bifunctional organocatalyst. The hydroxamic acid component with sterically hindered amide moiety is crucial for the successful formation and transformation of the N-amide isoxazolidin-5-ones obtained.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Organic
Ding Wang, Zhishuang Ma, Jin Xi, Nana Wang, Tao Wang, Yong Liang, Zunting Zhang
Summary: A concise and efficient method for the synthesis of chromeno[3,4-c]chromene-6,7-dione has been developed. The method demonstrates a broad substrate scope and good functional group tolerance, and the synthesized compounds exhibit blue-green fluorescence.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Medicinal
Syed Nasir Abbas Bukhari, Mohamed Abdelwahab Abdelgawad, Naveed Ahmed, Muhammad Wahab Amjad, Muhammad Ajaz Hussain, Mervat A. Elsherif, Hasan Ejaz, Nasser H. Alotaibi, Ignjat Filipovic, Nenad Jankovic
Summary: In this study, eight novel Meldrum's acid derivatives with various vanillic groups were synthesized and tested against cancer cell lines and microbes. Three of them showed excellent biological activity against E. coli, HeLa, and A549 cell lines. The O-alkyl substituted derivatives exhibited better antimicrobial and anticancer activities compared to the O-acyl ones. Compound 3i, with decyl substitution, demonstrated the highest activity against E. coli and cancer cell lines, with a selectivity index of 4.8 (HeLa). Molecular docking studies revealed that compound 3i had strong binding affinity to DNA, E. coli Gyrase B, and topoisomerase II beta, acting as a Michael acceptor for nucleophiles Lys and Ser. The topoisomerase II beta-LYS482-3i cluster showed the best E-b.
Article
Chemistry, Organic
Mengyang Shen, Jie Zhao, Yuanshuang Xu, Xinying Zhang, Xuesen Fan
Summary: This novel synthesis method of dihydroquinolinone derivatives involves an unprecedented cascade reaction, which includes the in-situ formation of aryne and its addition with pyrazolidinone, followed by N-N bond cleavage and intramolecular C-C bond formation. Compared to existing methods, this protocol offers advantages such as multiple transformations in one pot, a broad substrate scope, mild reaction conditions, and good tolerance of various functional groups. Additionally, the products obtained from this method demonstrated significant in vitro antiproliferative activity in selected human cancer cell lines.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Mengyang Shen, Yuanshuang Xu, Xinying Zhang, Xuesen Fan
Summary: A novel synthesis of spirocyclopropylpyrazole derivatives tethered with a trifluoromethyl unit has been developed through an unprecedented cascade reaction. In this reaction, alkylidenecyclopropanes, pyrazolidinones, and trifluoroethanol are used as starting materials. The reaction proceeds with air as an economical and sustainable oxidant. Compared to traditional methods, this new protocol offers advantages such as one-pot multi-step transformations, broad substrate scope, mild reaction conditions, good efficiency, and excellent atom-economy.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Biochemistry & Molecular Biology
Victor V. Dotsenko, Alexander V. Aksenov, Anna E. Sinotsko, Ekaterina A. Varzieva, Alena A. Russkikh, Arina G. Levchenko, Nicolai A. Aksenov, Inna V. Aksenova
Summary: The Michael addition reaction between dithiomalondianilide and arylmethylidene Meldrum's acids, along with subsequent heterocyclization, was investigated. The study also looked into the factors affecting the composition of the obtained products. The structure of one of the products was confirmed through X-ray crystallography.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2022)
Article
Chemistry, Multidisciplinary
Wei Liu, Tianren Qin, Wansen Xie, Jinmiao Zhou, Zidan Ye, Xiaoyu Yang
Summary: We have developed an efficient modular asymmetric synthesis of azahelicenes from readily available polycyclic aromatic amines, aldehydes, and (di)enamides, employing a central-to-helical chirality conversion strategy. A series of aza[5]- and aza[4]helicenes bearing various substituents were easily obtained with good yields and high enantioselectivities. The diverse derivatizations and the preliminary application of the azahelicene derivative as a chiral organocatalyst demonstrated the potential of this method, and the photophysical and chiroptical properties of these azahelicenes were well studied, showing potential applications in novel organic optoelectronic materials.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Min Liu, Haiying Zhao, Changkun Li
Summary: A highly regio- and enantioselective allylic alkylation of Meldrum acid with racemic allylic substrates bearing alkyl groups has been developed using a Rh(I) catalyst. The use of a chiral bisoxazopinephosphine ligand is essential for high yields and selectivities, providing rapid access to various chiral beta-alkyl-gamma,delta-unsaturated carboxylic acids and their derivatives.
CHINESE CHEMICAL LETTERS
(2021)
Article
Chemistry, Multidisciplinary
Eduard Badarau, K. Harsha Vardhan Reddy, Aurore Loudet, Charles Simon, Laurent Trembleau, Stijn Claerhout, Etienne Pair, Stephane Massip, Philippe Breton, Brigitte Lesur, Solo Goldstein, Jean-Marie Fourquez, Jean Michel Henlin, Leon Ghosez
CHEMISTRY-A EUROPEAN JOURNAL
(2020)
Review
Chemistry, Organic
Antonio Macchia, Andreas Eitzinger, Jean-Francois Briere, Mario Waser, Antonio Massa
Summary: Isoxazol-5-ones and isoxazolidin-5-ones are two important classes of heterocycles with various applications, and their asymmetric construction is particularly important. Chiral metal catalysts and organocatalysts have been successfully employed for the enantioselective synthesis of these heterocycles.
SYNTHESIS-STUTTGART
(2021)
Article
Chemistry, Multidisciplinary
Stephane Wittmann, Thomas Martzel, Cong Thanh Pham Truong, Martial Toffano, Sylvain Oudeyer, Regis Guillot, Chloee Bournaud, Vincent Gandon, Jean-Francois Briere, Giang Vo-Thanh
Summary: Through Bronsted base organocatalysis, ketone-derived alkylidene Meldrum's acids react with dihydro-2,3-furandione in a formal (4+2) cycloaddition reaction, yielding 3,6-dihydropyran-2-ones with up to 98% ee. This reaction can be extended to other activated ketones, making alkylidene Meldrum's acids a novel C4-synthon in the vinylogous series.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Applied
Martial Toffano, Regis Guillot, Chloee Bournaud, Jean-Francois Briere, Giang Vo-Thanh
Summary: A catalytic enantioselective vinylogous domino reaction has been successfully achieved, providing spirolactone dihydropyranones with high enantiomeric excess. The reaction involves an Auto Tandem Catalysis (ATC) process facilitated by the dual and complementary role of (DHQ)(2)PHAL organocatalyst, leading to good yields and high selectivity.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Applied
Julien Annibaletto, Thomas Martzel, Vincent Levacher, Sylvain Oudeyer, Jean-Francois Briere
Summary: The strategy reported involves a multicomponent catalytic enantioselective synthesis of beta-substituted isoxazolidin-5-ones via a KMC process promoted by a suitable bifunctional organocatalyst. The hydroxamic acid component with sterically hindered amide moiety is crucial for the successful formation and transformation of the N-amide isoxazolidin-5-ones obtained.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Organic
Arthur Lebrene, Thomas Martzel, Laura Gouriou, Morgane Sanselme, Vincent Levacher, Sylvain Oudeyer, Carlos Afonso, Corinne Loutelier-Bourhis, Jean-Francois Briere
Summary: A straightforward method for synthesizing original 1,6-diazabicyclo[4.3.0]nonane-2,7-diones was developed using a DBU-organocatalyzed multicomponent Knoevenagel-aza-Michael-Cyclocondensation reaction. Analysis of key reactive intermediates using mass spectrometry confirmed the proposed mechanism.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Review
Chemistry, Physical
Claire Segovia, Pierre-Antoine Nocquet, Vincent Levacher, Jean-Francois Briere, Sylvain Oudeyer
Summary: This review summarizes the achievements in the field of organocatalyzed nucleophilic dearomatization of azaarenium salts, highlighting the versatility of the approach through classification of different activation modes and discussion of chemical transformations of the resulting products.
Article
Chemistry, Applied
Claire Segovia, Jeremy Godemert, Jean-Francois Briere, Vincent Levacher, Sylvain Oudeyer
Summary: An organocatalyzed one-pot sequential deracemization of aromatic ketones with a stereogenic center at the alpha-position was achieved through an acid-base strategy, in which enantioselective protonation reaction played a key role. This protocol provides enantioenriched ketones with up to 89% ee without isolating sensitive intermediates like silyl enolates. Water was found to be crucial in this process. This one-pot sequence serves as a valuable extension to previously reported chemically driven red-ox protocols, expanding the range of molecules eligible for deracemization.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Multidisciplinary
Philippe Champetter, Ismail Alahyen, Catherine Taillier, Jean-Francois Briere, Vincent Dalla, Sylvain Oudeyer, Sebastien Comesse
Summary: The study aims to compare the impact of N-alkoxy and N-alkyl moieties in domino reactions, finding that N-alkoxy exhibits higher reactivity and efficiency, leading to a wider range of products under milder conditions.
Article
Chemistry, Applied
Anais Coffinet, Vincent Levacher, Isabelle Gillaizeau, Jean-Francois Briere, Sylvain Oudeyer
Summary: A metal-catalyzed cyanomethylation of isatins and activated ketones using Ni-II-complexes with a pyridine(dicarboxamide) pincer ligand is reported. High isolated yields (up to 99%) were obtained at room temperature with various acetonitrile derivatives. The involvement of cation part (Cs+ or n-Bu4N+) likely enhances the formation and catalytic activity of the proposed ion paired catalysts [NiCR2CN](-)Cat(+).
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Review
Biochemistry & Molecular Biology
Sylvain Oudeyer, Vincent Levacher, Helene Beucher, Jean-Francois Briere
Summary: Recently, there have been significant advancements in radical chemistry in the field of organic synthesis. The use of modern catalytic and technology-driven strategies has allowed for the implementation of highly reactive radical species, expanding the scope of synthetic methodologies. This literature review focuses on the recent progress in radical-based transformations of N,N-disubstituted iminium substrates and the chemistry of N+-X-(X = O, NR) azaarenium dipoles, which have proven to be versatile platforms in this research field. The specific reactivity profiles of N-alkylazaarenium salts in radical chemistry are also discussed.
Article
Chemistry, Multidisciplinary
Pierre Milbeo, Arthur Lebrene, Mariia Savchuk, Giang Vo-Thanh, Sylvain Oudeyer, Helene Beucher, Jean-Francois Briere
Summary: A highly diastereoselective organocatalyzed domino vinylogous sulfa-Michael-aldol-cyclocondensation (VMAC) reaction has been developed using alkylidene Meldrum's acid as dienes, showcasing an unprecedented sulfa-1,6-conjugate addition and a diastereoselective aldol reaction leading to a formal (4+2) cycloaddition. This research provides a new approach to synthesize bio-relevant and original tricyclic thiochroman derivatives.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Biochemistry & Molecular Biology
Corentin Maret, Nicolas David, David Pierrot, Eric Leonel, Vincent Levacher, Jean-Francois Briere, Sylvain Oudeyer
Summary: The electrocarboxylation of alpha,alpha-dichloroarylmethane derivatives in the presence of CO2 was achieved, resulting in the formation of alpha-chloroarylacetic acid derivatives with high selectivity. These derivatives were found to be versatile intermediates in synthetic chemistry and underwent various chemical transformations. A proposed mechanism was supported by control experiments and cyclic voltammetry.
Article
Chemistry, Multidisciplinary
Ludovic Leleu, Thomas Martzel, Arona Fall, Morgane Sanselme, Vincent Levacher, Sylvain Oudeyer, Jean-Francois Briere
Summary: By utilizing metal- and catalyst-free electrochemical conditions in an undivided cell, a series of easily available redox-active N-(acyloxy)phthalimide esters were reacted with chiral C5-substituted azomethine imines, resulting in an efficient and highly stereoselective addition reaction to produce an array of polyaminated hydrazine derivatives.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Multidisciplinary
Emmanuel Deau, Alexandra Le Foll, Clemence Fouache, Emilie Corrot, Laetitia Bailly, Vincent Levacher, Pierric Marchand, Florian Querniard, Laurent Bischoff, Jean-Francois Briere
Summary: An unprecedented enantioselective conjugate addition reaction of sodium bisulfite to various nitrostyrenes was achieved with the influence of a bifunctional amino-thiourea organocatalyst, leading to a straightforward route to unprotected chiral taurine derivatives by reducing the obtained beta-nitroethanesulfonic acids into the corresponding amino derivatives.
CHEMICAL COMMUNICATIONS
(2021)
Review
Chemistry, Multidisciplinary
Dan He, Yawen Li, Fuwen Zhao, Yuze Lin
Summary: High trap density in organic solar cells leads to localized charge carriers and reduced carrier lifetime, limiting device efficiency. This feature article summarizes the recent advances of trap suppression by material design and device engineering.
CHEMICAL COMMUNICATIONS
(2024)
Review
Chemistry, Multidisciplinary
Olivier Monfort, Arshitha Madhusudhan, Martin Motola
Summary: This article presents the advantages of coupling photocatalysis and Fenton-based processes for environmental remediation and discusses their synergy. It critically examines the simultaneous triggering of these two processes and provides insights into research approaches. The study aims to enhance understanding of this complex process and highlight the potential integration of new catalysts in current wastewater treatment technology.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Manideepa Dhar, Chittaranjan Mishra, Avijit Das, Uttam Manna
Summary: An approach of 'polymerization of monomers in its aggregated form' has been introduced to tailor the water wettability of fibrous and porous substrates, achieving hydrophobicity to superhydrophobicity transition, as well as patterned wettability. This facile chemical method provides a durable coating with adjustable and patterned wettability for various potential applications.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Saswat Ranjan Bhoi, Chhanda Debnath, Shikha Gandhi
Summary: In this article, a novel catalytic reaction using Pd(0) and Bronsted acid is reported for the synthesis of biologically important imidazolidinone-fused N-heterocycles through redox-neutral intramolecular N-allylation of indoles and pyrroles with alkynes. This atom-economical method is applicable to a wide range of substrates and eliminates the need for leaving groups or oxidizing agents commonly used in traditional allylation reactions.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Longkun Chen, Mingshuai Zhang, Meichen Liu, Zhuoyuan Liu, Yuetong Qiu, Zhilai Zhang, Fuchao Yu, Jiuzhong Huang
Summary: In this study, an efficient Rh(III)-catalyzed selective mono- and dual-C-H bond functionalization/cyclization with iodonium ylide as the sole coupling partner was demonstrated. Fused benzodiazepine skeletons were obtained in excellent yields, providing an improved approach to dual C-H unsymmetrical functionalization.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Alice Kennett, Sven Epple, Gabriella van der Valk, Irene Georgiou, Evelyne Gout, Romain R. Vives, Angela J. Russell
Summary: This study presents the design and synthesis of sulfated disaccharide inhibitors based on IdoA(2S)-GlcNS(6S), which showed potent inhibition of Sulf-2. The results suggest that IdoA(2S)-GlcNS(6S) is the shortest fragment size required for effective inhibition of Sulfs, and a trisulfated disaccharide is identified as the minimal fragment size of heparan sulfate for effective endosulfatase inhibition.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Mauro Garbini, Andrea Brunetti, Riccardo Pedrazzani, Magda Monari, Massimo Marcaccio, Giulio Bertuzzi, Marco Bandini
Summary: The self-adaptability of galvanostatic electrolysis was found to be helpful in a multistage chemo- and diastereoselective electrochemically promoted cyclodimerization of chalcones. Through a series of reductive events, densely functionalized cyclopentanes with five contiguous stereocenters were obtained (25 examples, yields up to 95%, dr values up to >20:1). Further experimental and electrochemical investigations indicated the crucial role of dynamic kinetic resolution of the aldol intermediate in the reaction mechanism.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Dhananjay S. Nipate, Neha Meena, Prakash N. Swami, Krishnan Rangan, Anil Kumar
Summary: In this study, the synthesis of functionalized benzo[a]phenazines and indazolo[2,3-a]quinolines was achieved through Rh(III)-catalyzed oxidative annulation of 2-arylquinoxalines and 2-aryl-2H-indazoles with allyl alcohols. The method showed a wide substrate scope, excellent functional group tolerance, good to high yields of annulated products, and the capability for scaled-up synthesis. A tentative mechanism of the annulation reaction was proposed based on a preliminary mechanistic investigation.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Ruonan Zhang, Abudukadi Tudi, Xia Yang, Xuping Wang, Zhihua Yang, Shujuan Han, Shilie Pan
Summary: A new lead tellurium borate material with a unique fundamental building block [B4O10] was synthesized and found to exhibit high birefringence. The structure-property relationship was discussed using first-principles calculations.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Amresh Kumar Singh, Baishali Thakurta, Anupam Giri, Monalisa Pal
Summary: This study introduces three key concepts for the quick synthesis of large-scale high-quality 2D materials films and their utilization in device fabrication.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Reina Hagiwara, Shun Nishimura, Kosuke Okeyoshi
Summary: A copolymer-conjugated nanocatalytic system has been developed to improve electron transfer and enhance photoinduced H2 generation.
CHEMICAL COMMUNICATIONS
(2024)
