Article
Chemistry, Multidisciplinary
Pengfei Zhao, Peiyuan Li, Jian Xiao, Yali Wang, Xiaohui Hao, Aiguo Meng, Chunyan Liu
Summary: Inspired by the diverse bioactivities of alpha-amino phosphine oxides, an efficient strategy for the synthesis of less researched alpha-(hydroxyamino)diarylphosphine oxides has been developed and their antitumor activities are explored. The reaction, carried out under water and catalyst-free conditions, shows high yields and features a wide substrate scope, facile starting materials, atom economy, and easy purification. Moreover, two synthesized derivatives 5e and 5f exhibit potential as anti-cancer agents for further development, as revealed by biological evaluation.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Pablo Macias-Benitez, Alfonso Sierra-Padilla, Manuel J. Tenorio, F. Javier Moreno-Dorado, Francisco M. Guerra
Summary: The study utilized microwave irradiation to promote the oxyphosphorylation of alkynes with diethyl phosphite and t-butyl hydroperoxide in the presence of [Cu(MeCN)(4)]BF4, yielding different phosphonylated indenones.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Fu-Peng Wu, Yuan Yang, Dilver Pena Fuentes, Xiao-Feng Wu
Summary: Carbonylation reactions are important in contemporary organic chemistry as they provide access to compounds with carbon monoxide or methyl groups. We report a copper-catalyzed carbonylative catenation and borylation reaction and propose a possible reaction mechanism.
Article
Chemistry, Multidisciplinary
Elise Ane Maluf Rios, Carla M. B. Gomes, Gabriel L. Silverio, Eduardo Q. Luz, Sher Ali, Caroline da Ros Montes D'Oca, Breidi Albach, Renan B. Campos, Daniel S. Rampon
Summary: In this article, the Ag(i)-catalyzed direct selanylation of indoles with diorganoyl diselenides is described. The reaction efficiently yielded 3-selanylindoles with high regioselectivity, and it also provided direct access to 2-selanylindoles through a Plancher rearrangement-like process when the C3 position of the indole ring was blocked. Experimental analyses and density functional theory calculations were employed to elucidate the reaction mechanism. Among the considered pathways, our findings support a classic electrophilic aromatic substitution via Lewis adducts between Ag(i) and diorganoyl diselenides. The results also offer new insights into the interactions between Ag(i) and diorganoyl diselenides.
Article
Chemistry, Organic
Fang Fang, Haolin Zheng, Guojiang Mao, Shanping Chen, Guo-Jun Deng
Summary: A novel strategy for the preparation of functional carbazoles has been developed using a catalytic reaction. The method utilizes easily available raw materials and achieves high yields under metal- and solvent-free conditions.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Applied
Hayeon Kwak, Eunsu Kang, Jae Yeong Song, Geunhee Kang, Jung Min Joo
Summary: The development of modular approaches for heteroaromatic cores and substituents is crucial for drug candidates and organic functional materials. A new strategy involving the cyclization of heteroarenes tethered with alkynes through a norbornene bridge was developed. The Pd catalytic system transformed a variety of five-membered heteroarenes to the corresponding benzofused products, demonstrating its versatility in the annulation of (hetero)aromatic rings.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Organic
Rajshekhar A. Unhale, Milon M. Sadhu, Vinod K. Singh
Summary: A novel organocatalytic asymmetric formal [3 + 2] cycloaddition has been developed for the synthesis of biologically relevant chiral spiroisoindolinone-indolines with excellent yields and enantioselectivity under mild conditions.
Article
Chemistry, Multidisciplinary
Bidhan Ghosh, Satabdi Bera, Pintu Ghosh, Rajarshi Samanta
Summary: An efficient Rh(iii)-catalyzed strategy has been developed for the synthesis of quinoline braced cyclophane macrocycles via methyl (sp(3)) C-H functionalization, which is mild, simple, regioselective, and tolerates various functional groups with different ring sizes. The method involves C8-methyl metalation, metal-carbene formation, and migratory insertion, with high dilution not necessary and nitrogen being the only byproduct. Preliminary investigation suggests that the C-H metalation step is the rate-determining step.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Multidisciplinary
Tobias Kaper, Dennis Geik, Felix Fornfeist, Marc Schmidtmann, Sven Doye
Summary: Intermolecular hydroaminoalkylation reactions of symmetrical and unsymmetrical alkynes with tertiary amines were achieved with catalytic amounts of TiBn4, Ph3C[B(C6F5)(4)], and a sterically demanding aminopyridinato ligand precursor. The resulting products, synthetically and pharmaceutically useful tertiary beta,gamma-disubstituted allylic amines, were obtained in high yields and excellent stereoselectivity. The fact that even the industrial side product trimethylamine can be used as a substrate is particularly promising for future applications.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Biochemistry & Molecular Biology
Igor Philippov, Yuriy Gatilov, Alina Sonina, Aleksey Vorob'ev
Summary: A method for the synthesis of pyrazolo[1,5-a]pyridine-3-ylphosphonates by oxidative [3+2]cycloaddition reaction was reported. Different substituents have an effect on the reaction activity, with 4-halogenated substituents showing lower reactivity.
Article
Chemistry, Organic
Bin Zhao, Gerald B. Hammond, Bo Xu
Summary: The method involves using inexpensive aromatic ketone photocatalysts to synthesize imidazo-isoquinolinone derivatives, tolerating a wide range of functional groups and working well for both alkyl and aryl radicals.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Chunyu Han, Xianhai Tian, Huili Zhang, Frank Rominger, A. Stephen K. Hashmi
Summary: A gold-catalyzed synthesis of tetrasubstituted 1,3-enynes from hypervalent iodine(III) reagents and activated alkenes is reported, offering 26 enynes in 62-92% yield with excellent functional group tolerance. This reaction involves an in situ formed alkynyl Au(III) species and a subsequent direct C(sp(2))-H functionalization of alkenes.
Article
Chemistry, Organic
Lin Li, Xin-Lian Liu, Jin-Yan Liang, Yong-Yu He, Ai-Jun Ma, Wei-Feng Wang, Jin-Bao Peng
Summary: A palladium-catalyzed dicarbonylation reaction of alpha-iodo-substituted ACPs has been developed for the synthesis of carbamoyl-substituted indenones. Two carbonyl groups are incorporated into the product by cleaving the proximal C-C bond of the ACPs. A broad range of carbamoyl-substituted indenones are efficiently prepared with good to excellent yields.
Article
Chemistry, Organic
Juntao Yang, Bingxian Liu, Junbiao Chang
Summary: A ruthenium(II)-catalyzed one-pot synthesis of highly substituted 1,2-dihydropyridines (DHPs) via a three component reaction system has been successfully developed. The reaction utilizes a simple Ru(II) catalyst without the need for specific ligands. The catalytic system shows excellent functional group compatibility with a wide range of starting materials. The obtained DHPs can be easily converted into tetrahydropyridines and azabicyclo[4.2.0]octa-4,7-dienes by subsequent reduction or [2 + 2] cycloaddition reaction.
Article
Chemistry, Organic
Jia-Yin Wang, Sai Zhang, Yao Tang, Shenghu Yan, Guigen Li
Summary: The Cu(I)-catalyzed annulation-halotrifluoromethylation and cyanotrifluoromethylation of enynones have been successfully developed, allowing for the construction of quaternary carbon-centered 1-indanones through multibond formations with moderate to good chemical yields. The reaction of enynones with Togni's reagent and chloro- or bromotrimethylsilane yielded halo- and CF3-containing 1-indenones, while the addition of K3PO4 as a base resulted in the formation of cyano-anchored (Z)-1-indanones as the major stereoisomeric products. This strategy exhibits excellent compatibility with a wide range of enynones.
Article
Chemistry, Physical
Yanina Moglie, Eduardo Buxaderas, Agustina Mancini, Francisco Alonso, Gabriel Radivoy
Article
Chemistry, Physical
Grigoriy N. Bondarenko, Ekaterina G. Dvurechenskaya, Olga G. Ganina, Francisco Alonso, Irina P. Beletskaya
APPLIED CATALYSIS B-ENVIRONMENTAL
(2019)
Article
Biochemistry & Molecular Biology
Fabian Santana-Romo, Carlos F. Lagos, Yorley Duarte, Francisco Castillo, Yanina Moglie, Miguel A. Maestro, Nitin Charbe, Flavia C. Zacconi
Article
Nanoscience & Nanotechnology
Alexander V. Sirotkin, Monika Radosova, Adam Tarko, Iris Martin-Garcia, Francisco Alonso
Article
Chemistry, Multidisciplinary
Alexander Sirotkin, Monika Radosova, Adam Tarko, Zuzana Fabova, Iris Martin-Garcia, Francisco Alonso
Article
Chemistry, Multidisciplinary
Luciano A. Benedini, Yanina Moglie, Juan M. Ruso, Sofia Nardi, Paula Messina
Summary: This study evaluates the chemical grafting of phosphorous amide and alpha-amino phosphonate molecular fragments on previously created biomimetic hydroxyapatite nanoparticles, providing a new application for the liquid crystal properties of biological molecular networks. The results demonstrate that under specific synthetic conditions, it is possible to obtain nanoparticles that act as mesogenic agents and self-assemble under pH stimulation.
CRYSTAL GROWTH & DESIGN
(2021)
Article
Chemistry, Multidisciplinary
Yanina Moglie, Evangelina Mascaro, Flavia Zacconi, Gabriel Radivoy
Summary: Copper nanoparticles supported on ZnO exhibit high activity and selectivity in the N-arylation of cyclic and acyclic amides, with mild reaction conditions and the ability to be reused multiple times without significant loss of activity. The methodology can also be successfully scaled up to gram scale without diminishing catalytic activity.
Review
Chemistry, Multidisciplinary
Diego F. Rodriguez, Yanina Moglie, Cesar A. Ramirez-Sarmiento, Sachin Kumar Singh, Kamal Dua, Flavia C. Zacconi
Summary: The fields of click chemistry and biocatalysis have grown rapidly, leading to significant interactions between these two fields. Bio-click chemistry, which combines biocatalytic enzyme activity with click reactions, offers a green and sustainable approach for the synthesis of high-value molecules, particularly chiral molecules with applications in medicinal chemistry and sustainable syntheses.
Article
Pharmacology & Pharmacy
Diego F. Rodriguez, Francisca Duran-Osorio, Yorley Duarte, Pedro Olivares, Yanina Moglie, Kamal Dua, Flavia C. Zacconi
Summary: Implementation of green chemistry has shown promising results in waste reduction in the pharmaceutical industry. However, sustainable development of pharmaceutically active compounds and ingredients remains challenging. In this study, a green synthesis method was used to produce pharmaceutically active peptide triazoles as potent factor Xa inhibitors, important drug targets for cardiovascular diseases. The synthesis involved cycloaddition reactions with high atom economy, microwave-assisted organic synthesis for energy efficiency, and copper nanoparticle catalysis with Earth-abundant metals. The synthesized molecules demonstrated FXa inhibition with low IC50 values and no cytotoxicity in HEK293 and HeLa cells, highlighting the environmental potential and chemical implications of the applied methodologies for new molecule development.
Article
Biochemistry & Molecular Biology
Jose J. Delgado-Marin, Iris Martin-Garcia, David Villalgordo-Hernandez, Francisco Alonso, Enrique Ramos-Fernandez, Javier Narciso
Summary: One potential way to utilize CO2 is to react it with organic epoxides to produce cyclic carbonates. However, no efficient and selective heterogeneous catalyst has been discovered yet. In this study, cobalt and zinc-based zeolitic imidazole frameworks (ZIFs) were explored as catalysts for this reaction. Modified ZIF-8 and ZIF-67 catalysts were prepared and showed excellent catalytic performance in the cycloaddition of CO2 with epichlorohydrin. Notably, these reactions occurred under mild conditions without the need for co-catalysts.
Article
Biochemistry & Molecular Biology
Mahzad Yaghmaei, Martin Villanueva, Iris Martin-Garcia, Francisco Alonso, Xiaocong Zhang, Neeraj Joshi, Anabel E. Lanterna, Juan C. Scaiano
Summary: Selective semi-oxidation of tetrahydroisoquinoline (THIQ) can be achieved through singlet oxygen photooxidation process, leading to a valuable dihydroisoquinoline (DHIQ) derivative. Photosensitisers can activate the reaction even under heterogeneous conditions and can be combined with semiconductor catalysts to improve reaction efficiency and catalyst separability and reusability.
PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES
(2022)
Article
Chemistry, Physical
Iris Martin-Garcia, Gloria Diaz-Reyes, George Sloan, Yanina Moglie, Francisco Alonso
Summary: Sulfur has been found to be an effective stabilizing agent for copper nanoparticles, allowing for their application in organic medium catalytic reactions; The Cu(2)ONPs/S-8 system shows promising results in solvent-free aerobic oxidation of primary amines to imines, with potential for various applications; A proposed reaction mechanism based on experimental evidence provides insight into key intermediates, suggesting new research avenues in nanocatalysis.
JOURNAL OF MATERIALS CHEMISTRY A
(2021)
Review
Chemistry, Organic
Irene Bosque, Rafael Chinchilla, Jose C. Gonzalez-Gomez, David Guijarro, Francisco Alonso
ORGANIC CHEMISTRY FRONTIERS
(2020)
Review
Chemistry, Multidisciplinary
Francisco Alonso, Irene Bosque, Rafael Chinchilla, Jose Carlos Gonzalez-Gomez, David Guijarro
CURRENT GREEN CHEMISTRY
(2019)