Article
Chemistry, Organic
Qing-Qiang Su, Ruo-Nan Wang, Yong-Zheng Lv, Ya-Xin Fan, Shan Li, Hong-Li Huang, Ji-Yuan Du
Summary: This study presents a one-pot cycloaddition reaction of ethynyl indoloxazolidones with 1,3-cyclohexanediones enabled by copper catalysis, leading to a series of functionalized furan derivatives in good yields. The method demonstrates mild reaction conditions, high efficiency, and wide substrate scope.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Physical
Melissa Cadena, Roberto Silva Villatoro, Jyoti Shah Gupta, Cody Phillips, Jonathan B. Allen, Hadi D. Arman, Daniel J. Wherritt, Nicholas A. Clanton, Alexander L. Ruchelman, Eric M. Simmons, Albert J. DelMonte, John R. Coombs, Doug E. Frantz
Summary: A highly chemoselective Pd-catalyzed O-benzylation reaction has been discovered and developed, and the reaction mechanism has been analyzed in detail. This method allows for selective O-alkylation of 2-quinolinones with various functional groups, providing high yields and good selectivity.
Article
Chemistry, Physical
Melissa Cadena, Roberto Silva Villatoro, Jyoti Shah Gupta, Cody Phillips, Jonathan B. Allen, Hadi D. Arman, Daniel J. Wherritt, Nicholas A. Clanton, Alexander L. Ruchelman, Eric M. Simmons, Albert J. DelMonte, John R. Coombs, Doug E. Frantz
Summary: We have developed a highly selective Pd-catalyzed O-benzylation reaction and identified the formation of a key intermediate through detailed reaction analysis. This method enables the selective O-alkylation of substituted 2-quinolinones with high efficiency using a minimal amount of Pd catalyst.
Article
Chemistry, Organic
Giacomo Mari, Matteo Corrieri, Lucia De Crescentini, Gianfranco Favi, Stefania Santeusanio, Fabio Mantellini
Summary: Substituted 1-aminopyrroles can be easily accessed through an iron-catalyzed cascade reaction of 1,2-diaza-1,3-dienes, which involves a [4+2] cyclodimerization and ring contraction process. The presence of activated hydrogen in the terminal position of the azo-enic moiety is crucial for the synthesis of pyrroles.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Physical
Emely Jockmann, Fabiana Subrizi, Michael K. F. Mohr, Eve M. Carter, Pia M. Hebecker, Desiree Popadic, Helen C. Hailes, Jennifer N. Andexer
Summary: S-Adenosyl-l-methionine (SAM)-dependent methyltransferases (MTs) are a chemoselective and environmentally friendly alternative to synthetic methylating reagents. In this study, the substrate range and chemoselectivity of RgANMT and PpCaOMT were investigated, and cofactor derivatives were used to transfer alkyl chains onto aminophenols, leading to an increased pool of products.
Review
Chemistry, Organic
Tauqir Ahmad, Nisar Ullah
Summary: The oxa-Michael reaction is an effective and straightforward method for synthesizing a variety of oxygen-containing heterocycles, frequently found in biologically active substances. Organocatalytic asymmetric OMR has enabled the synthesis of diverse oxygen-containing heterocycles with high enantio- and/or diastereoselectivity.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Multidisciplinary
Hongmei Qin, Qimei Xie, Long He
Summary: This study developed a simple and convenient method to synthesize functionalized chroman-spirobenzofuran-2-one scaffolds via oxa-Michael/1,6-conjugated addition, providing an efficient strategy for constructing desired spirocyclic compounds.
Article
Chemistry, Medicinal
Lu Lin, Shunsuke Kataoka, Kiichi Hirayama, Ryozo Shibuya, Hiroyuki Morimoto, Takashi Ohshima
Summary: Catalytic control of chemoselectivity is crucial in the synthesis of highly functionalized compounds. In this study, highly O- and N-selective electrophilic activation of allylic alcohols and amines was achieved in Pd-catalyzed direct allylic alkylation. The N- selectivity is due to the selective activation of allylic amines with ammonium cations, and boronate formation accelerates the activation of allylic alcohols.
CHEMICAL & PHARMACEUTICAL BULLETIN
(2023)
Article
Biochemistry & Molecular Biology
Manickam Bakthadoss, Vishal Agarwal, Thirupathi Reddy Tadiparthi, Mushaf Mohammad
Summary: Chemoselective domino ring opening and selective O/S-alkylation of ethers/thioethers over enol C/O alkylation have been observed, resulting in the efficient conversion of various 2-aryl chromanones/thiochromanones with alkyl/allyl bromides into highly functionalized ethers and thioethers with excellent yields and high selectivity.
MOLECULAR DIVERSITY
(2021)
Article
Chemistry, Organic
Izamara Casadia, Thalita O. Daher, Sidnei Moura, Davi F. Back, Eliandro Faoro, Cristiane S. Schwalm, Gleison A. Casagrande, Guilherme C. Paveglio, Lucas Pizzuti
Summary: A convenient domino route for the synthesis of novel 1,3-dihydrofuro[3,4-c]pyridines from pyridoxal and alkyl, aryl or heteroaryl ketones under basic conditions is reported. Nine derivatives were obtained in yields ranging from 53% to 90% after stirring reactants for 48 hours at room temperature. The products were easily isolated by filtration followed by recrystallization from ethanol.
SYNTHESIS-STUTTGART
(2021)
Article
Chemistry, Organic
Mei-Lin Tang, Jin-Feng Ning, Yu-Hui Li, Heyanhao Zhang, Mi Liu, Ye-Jun Dong, Jun Chang
Summary: This paper presents an easy-operational, high-yielding method for the gram-scale synthesis of flavones using a one-pot sulfoxide-mediated condensation/annulation/elimination process. The synthetic route efficiently establishes flavones through a formal (5 + 1) cycloaddition, forming one CAO bond and one double C@C bond. Compound 7bn shows potential as a starting point for the development of anti-aging drugs.
TETRAHEDRON LETTERS
(2023)
Article
Chemistry, Organic
Silvia Vera, Ana Vazquez, Ricardo Rodriguez, Sandra Del Pozo, Inaki Urruzuno, Abel de Cozar, Antonia Mielgo, Claudio Palomo
Summary: This study reports a highly enantio- and syn-selective synthesis of beta-hydroxy alpha-amino acids from glycine imine derivatives under Bronsted base catalysis. The key lies in the use of benzophenone-derived imine of glycine o-nitroanilide as a pronucleophile, where the o-nitroanilide framework provides an efficient hydrogen-bonding platform that accounts for nucleophile reactivity and diastereoselectivity.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Long Wen, Pan Tang, Hao-Jie Ma, Jin-Yao Ren, Yi Yang, Yan Jiang
Summary: A highly diastereoselective Michael addition/ketalization reaction catalyzed by GaCl3 has been achieved, leading to the synthesis of biologically important indole-annulated compounds. Gram-scale reaction and chemical transformation of the resulting product have also been carried out to extend the synthetic utility and structural complexity.
TETRAHEDRON LETTERS
(2022)
Article
Chemistry, Multidisciplinary
Xueyan Liu, Jing Sun, Chao-Guo Yan
Summary: In this study, a three-component reaction was efficiently catalyzed by triethylamine to synthesize unique 8a 14-(epoxymethano)indeno[1',2':2,3]chromeno[4,3-a]pyrrolizines in ethanol. Furthermore, a four-component reaction promoted by a base produced N,O,S-containing polyheterocyclic compounds. The reaction mechanism involves the cascade reaction process of in situ generation of a special kind of azomethine ylide and annulation of phenoxide.
NEW JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Organic
Mehran Khoshbakhsh Foumani, Juergen Conrad, Wolfgang Frey, Uwe Beifuss
Summary: This study successfully achieved the selective reaction of five-, six-, seven-, and eight-membered cyclic 1-bromoallyl tosylates with 1,3-dicarbonyls using Cu(I) catalyst, resulting in a variety of bisannulated 4H-pyrans. In addition, using six-membered cyclic 1-bromoallyl tosylates and acyclic beta-ketoesters as substrates, corresponding 5,6,7,8-tetrahydro-4H-chromene-3-carboxylates can be obtained.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Alena Fedotova, Evgeniy Kondrashov, Julien Legros, Jacques Maddaluno, Alexander Yu. Rulev
COMPTES RENDUS CHIMIE
(2018)
Article
Chemistry, Multidisciplinary
David Reyes Loya, Michael De Paolis
CHEMISTRY-A EUROPEAN JOURNAL
(2019)
Article
Chemistry, Organic
Alexandre Jean, Jacques Rouden, Jacques Maddaluno, Michael De Paolis, Jerome Blanchet
TETRAHEDRON LETTERS
(2019)
Article
Chemistry, Multidisciplinary
Leo Birbaum, Laurent Gillard, Helene Gerard, Hassan Oulyadi, Guillaume Vincent, Xavier Moreau, Michael De Paolis, Isabelle Chataigner
CHEMISTRY-A EUROPEAN JOURNAL
(2019)
Article
Chemistry, Organic
Masahiro Abe, Alexandre Jean, Jerome Blanchet, Jacques Rouden, Jacques Maddaluno, Michael De Paolis
JOURNAL OF ORGANIC CHEMISTRY
(2019)
Article
Chemistry, Organic
Masahiro Abe, Baptiste Picard, Michael De Paolis
Article
Chemistry, Multidisciplinary
Matthieu Hedouin, Anne-Laure Barthelemy, Nicolas Vanthuyne, Hend Besrour, Jacques Maddaluno, Emmanuel Magnier, Hassan Oulyadi
Summary: This work explains the importance of using an excess of butyllithium in the directed ortho-lithiation of a trifluoromethyl sulfoximine. The study shows that the presence of excess n-BuLi leads to deprotonation on the ortho-position of the aromatic, resulting in the formation of six different aggregates. DFT calculations provide optimized solvated structures for these aggregates that are consistent with the experimental NMR data.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Morgan Cormier, Florian Hernvann, Michael De Paolis
Summary: A convergent approach to the skeleton of tridachiapyrone B was described in this study. This approach took advantage of the desymmetrization of alpha,alpha'-dimethoxy-gamma-pyrone to synthesize alpha-crotyl-alpha'-methoxy-gamma-pyrone in one step. The construction of the quaternary carbon of the 2,5-cyclohexa-dienone of the target was achieved through a strategy based on the Robinson-type annulation. The grafting of the simplified target's side chain was also demonstrated through an oxidative anionic oxy-Cope rearrangement.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Antoine d'Aleman, Oscar Gayraud, Catherine Fressigne, Emilie Petit, Laetitia Bailly, Jacques Maddaluno, Michael De Paolis
Summary: The lactonization of 2-(2-nitrophenyl)-1,3-cyclohexanediones containing an alcohol side chain and up to three distant prochiral elements is achieved through isomerization mediated by simple organocatalysts such as quinidine. This reaction produces strained nonalactones and decalactone with up to three stereocenters in high er and dr (up to 99 : 1) through a process of ring expansion. Various distant groups, including alkyl, aryl, carboxylate, and carboxamide moieties, were investigated.
Review
Chemistry, Multidisciplinary
Batoul Rkein, Antoine Bigot, Leo Birbaum, Maxime Manneveau, Michael De Paolis, Julien Legros, Isabelle Chataigner
Summary: The article discusses the electrophilic reactivity of 3-nitroindole derivatives and their importance in drug discovery, particularly in the context of dearomatization processes. These compounds have become model substrates for electron-poor aromatic compounds in dearomatization strategies.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Matthieu Hedouin, Anne Harrison-Marchand, Jacques Maddaluno, Hassan Oulyadi
CHEMICAL COMMUNICATIONS
(2020)
Review
Chemistry, Organic
Baptiste Picard, Isabelle Chataigner, Jacques Maddaluno, Julien Legros
ORGANIC & BIOMOLECULAR CHEMISTRY
(2019)
Article
Chemistry, Organic
Pauline Chaumont-Olive, Jacques Maddaluno, Anne Harrison-Marchand
ORGANIC & BIOMOLECULAR CHEMISTRY
(2019)
Article
Chemistry, Organic
Faiza Diaba, Gisela Trenchs
Summary: The first violet light-mediated synthesis of gamma- and delta-lactams from N-alkenyl trichloroacetamides is reported in this paper. The reactions are conducted in tetrahydrofuran or 2-methyltetrahydrofuran as the sole solvent without catalysts or additives, under non-anhydrous conditions in an air atmosphere where the solvent serves as the radical initiator.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Feroze Hussain, Sajjad Ahmed, Ashiq Hussain Padder, Qazi Naveed Ahmed
Summary: This study reports a novel and efficient one-pot synthesis method for mixed phosphorotrithioates, which does not require supplementary additives and shows broad applicability.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Hyunjin Oh, Ikyon Kim
Summary: A new 1,2,4-triazole-pyrrolo[1,2-a]pyrazine hybrid system, 6-acylpyrrolo[1,2-a][1,2,4]triazolo[5,1-c]pyrazine, was synthesized using a catalyst-free method. This method involved sequential exposure of pyrrole-2-carbonitrile-derived substrates to DMF-DMA and acyl hydrazide, resulting in the formation of acylated pyrazine and 1,2,4-triazole rings, enabling the installation of various substituents at specific positions on the core skeleton.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Ming Yan, Si-fan Wang, Yong-po Zhang, Jin-zhong Zhao, Zhuo Tang, Guang-xun Li
Summary: Here we developed an efficient photocatalytic approach for the convenient preparation of sulfinamides. The reaction allows for the gram-scale preparation of sulfinamides and the one-pot synthesis of various sulfonyl amides.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Farzaneh Bandehali-Naeini, Zahra Tanbakouchian, Noushin Farajinia-Lehi, Nicolas Mayer, Morteza Shiri, Martin Breugst
Summary: Two tandem catalytic systems were developed for the synthesis of novel 3,4-disubstituted maleimides using the same Ugi adducts. Different maleimide structures can be synthesized using either Pd or Cu catalysis.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Tanya Raghava, Anjan Chattopadhyay, Subhadeep Banerjee, Nivedita Sarkar
Summary: Amine substitution of two ortho fluorine atoms of tetrafluoroterephthalonitrile through SNAr chemistry is easily achievable. But further fluorine substitution is only possible under forcing conditions, yielding valuable fluorophores for bioimaging.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Review
Chemistry, Organic
Anju Chadha, Santosh Kumar Padhi, Selvaraj Stella, Sowmyalakshmi Venkataraman, Thangavelu Saravanan
Summary: Alcohol dehydrogenases are enzymes that use cofactors for oxidation or reduction reactions of alcohols or carbonyl compounds. They are utilized in green chemistry and have applications in the production of pharmaceuticals. Recombinant enzymes have solved the challenge of producing purified enzymes in large quantities. Engineered alcohol dehydrogenases have been used in asymmetric synthesis in industry. Various methods have been established for regenerating expensive cofactors to make the enzymatic process more efficient and economically viable.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
