Article
Chemistry, Organic
Xue Li, Heyun Sheng, Qiuling Song
Summary: Here, a new method for synthesizing 2-aminobenzofuran 3-enes through the C-S insertion reaction of alkyne-tethered diazo compounds is reported. Metal carbene, as an active synthetic intermediate, plays a crucial role in organic synthesis. By utilizing the carbene/alkyne metathesis strategy, a novel donor carbene is generated in situ as a key intermediate with distinct reactions from the donor receptor carbene.
Review
Chemistry, Multidisciplinary
Lifen Peng, Zhiwen Yuan, Zilong Tang, Chunling Zeng, Xinhua Xu
Summary: Organic cycles are important in chemistry, pharmacology, and material science due to their unique properties. Thioalkynes have attracted increasing attention as a convenient source for constructing organic cycles. This review highlights the construction of organic cycles from thioalkynes, including the synthesis of 2H-azirines, cyclobutanes, and cyclopentenes. Thioalkynes can also be used to synthesize various other cyclic compounds. The review provides an overview of the methods for accessing organic cycles and presents detailed applications of thioalkynes as synthons for preparing organic cycles, with a focus on different types of organic cycles and their corresponding reaction mechanisms if available.
Review
Chemistry, Organic
Pascal Matton, Steve Huvelle, Mansour Haddad, Phannarath Phansavath, Virginie Ratovelomanana-Vidal
Summary: Metal-catalyzed [2+2+2] cycloaddition is a powerful method for the rapid construction of functionalized 6-membered carbo- and heterocycles with high functional group tolerance. The reaction is usually regio- and chemoselective, but challenges remain for intermolecular reactions involving multiple alkynes.
SYNTHESIS-STUTTGART
(2021)
Article
Chemistry, Organic
Hao Zeng, Xiaojie Fang, Zhiyi Yang, Chuanle Zhu, Huanfeng Jiang
Summary: A general and practical method for the synthesis of 5-trifluoromethylpyrazoles has been reported, using a coupling reaction between hydrazonyl chlorides and the industrial feedstock 2-bromo-3,3,3-trifluoropropene (BTP). This catalyst-free [3 + 2] cycloaddition shows high regioselectivity, mild conditions, high yields, scalability, broad substrate scope, and tolerance for various functional groups, with application in synthesizing key intermediates for an active agonist of sphingosine 1-phosphate receptor.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Peng He, Ye Wang, Yingge Gu, Lu Cheng, Yilin Zhu, Chengyu Wang, Yanzhong Li
Summary: An efficient and atom-economical synthesis method for the selective synthesis of 2,4- or 3,4-dicarbonylselenophenes has been developed. The method utilizes readily accessible substrates, commercially available elemental selenium, and exhibits good functional group tolerance.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Yifan Ouyang, Kaifu Wu, Wei Zhou, Qian Cai
Summary: An efficient and convenient method for the synthesis of pyrrole-fused tetracyclic skeletons is described in this study, utilizing CuI as a catalyst. The reaction involves tandem [3 + 2] cycloaddition and C-C coupling processes to form 7-membered cyclic ketones fused with pyrrole and biphenyl rings.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Inorganic & Nuclear
Leo Chaussy, Marion Delorme, Alexander Punter, Yannick Carissan, Jean-Luc Parrain, Muriel Amatore, Paola Nava, Laurent Commeiras
Summary: This study computationally and experimentally investigated the mechanism of cobalt cycloaddition reactions. Based on the nature of the reaction and the nature of the 2π partner, spiro-lactone and spiro-lactam complexes were successfully synthesized.
DALTON TRANSACTIONS
(2023)
Article
Chemistry, Inorganic & Nuclear
Leo Chaussy, Marion Delorme, Alexander Punter, Yannick Carissan, Jean-Luc Parrain, Muriel Amatore, Paola Nava, Laurent Commeiras
Summary: This study computationally investigates the molecular complexity of cobalt(iii) polycyclic complexes and examines the mechanisms and role of 2 pi partners in cobalt-mediated cycloaddition reactions. The proposed mechanisms were supported by experiments and predicted compounds were successfully synthesized.
DALTON TRANSACTIONS
(2023)
Article
Chemistry, Organic
Yujia Gao, Juan Zhang, Wenyu Shan, Weihong Fei, Jinzhong Yao, Weijun Yao
Summary: In this study, a trimerization reaction of gamma-aryl-3-butynoates was achieved through catalysis, leading to the formation of exocyclopentene derivatives with an allcarbon quaternary stereocenter. The reaction exhibited high stereoselectivity and enantioselectivity, delivering optically pure products with high enantiomeric excess values.
Article
Chemistry, Organic
Cong Guan, Jiabin Yin, Jian Ji, Jinhua Liu, Xiang Wu, Tong Zhu, Shunying Liu
Summary: A regioselective electrochemical C-H amination method using easily accessible ethers has been developed to synthesize N (2)-substituted 1,2,3-triazole. Multiple substituents, including heterocycles, were well-tolerated, and 24 examples were obtained in moderate to good yields. Control experiments and DFT calculations revealed that the electrochemical synthesis occurs through a N-tosyl 1,2,3-triazole radical cation process, promoted by single-electron transfer from the lone pair electrons of the aromatic N-heterocycle, and the desulfonation is responsible for the high N (2)-regioselectivity.
Article
Chemistry, Multidisciplinary
Wang Wang, M. Kevin Brown
Summary: In this study, we achieved the stereoselective construction of 3D bicyclic scaffolds and azetidine derivatives by modulating N-sulfonylimines, allowing for either [4+2]- or [2+2]-cycloaddition reactions. The utility of the method was demonstrated through further modulation of the resulting products. Mechanistic studies supported a reaction mechanism involving Dexter energy transfer.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Ryota Shimotsukue, Kohei Fujii, Yu Sato, Yuki Nagashima, Ken Tanaka
Summary: We have developed a rhodium-catalyzed intermolecular [2+2+2] cycloaddition reaction with excellent selectivity, producing chiral cyclohexadienylamines. The reaction involves the reaction of two arylacetylenes with a cis-enamide or a silylacetylene to yield the desired products with complete regio- and diastereoselectivity and high yields and enantioselectivity. Mechanistic studies suggest the formation of a rhodacyclopentadiene intermediate from the terminal alkynes.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Review
Chemistry, Multidisciplinary
Pietro Franceschi, Sara Cuadros, Giulio Goti, Luca Dell'Amico
Summary: The synthesis of four-membered heterocycles often requires complex procedures and prefunctionalized reactants. An alternative approach is the photochemical [2+2]-heterocycloaddition, but it is limited by the absorption profile of the carbonyl and the use of high-energy UV-light. This review highlights the progress made in developing visible light-driven [2+2]-heterocycloadditions and discusses the remaining challenges and potential future directions.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Huai-Ri Sun, Lan Yang, Yu Li, Le Yu, Bo-Bo Gou, Atif Sharif, Qing-Song Jian, Jie Chen, Ling Zhou
Summary: A chiral phosphoric acid was used as a catalyst for the enantioselective [2 + 2] cycloaddition reaction between alkynylindols or alkynylnaphthols and quinones. The reaction produced a class of functionalized cyclobutenes with high yields and excellent diastereo- and enantioselectivities. Mechanistic studies revealed the involvement of dearomatization of indole or naphthol and intramolecular Michael addition in the reaction, while preventing competitive [2 + 3] cycloaddition. During the transformation of the product, an interesting conversion from central to axial chirality was achieved through a rearrangement process.
SCIENCE CHINA-CHEMISTRY
(2023)
Article
Chemistry, Organic
Hyo Seon Sim, Hari Datta Khanal, Yong Rok Lee
Summary: In this paper, a highly efficient and atom-economic iron(III)-catalyzed three-component heteroannulation reaction is described for the construction of multifunctionalized 2-pyridones. The protocol allows rapid access to a variety of 2-pyridones with an ortho-hydroxybenzoyl and a benzoyl scaffold under simple conditions. The synthetic utility of the synthesized 2-pyridone scaffolds is demonstrated by transforming them into biologically interesting complex heterocycles.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Agustina La-Venia, Mirta P. Mischne, Ernesto G. Mata
Article
Biochemistry & Molecular Biology
Janos Gera, Titanilla Szogi, Zsolt Bozso, Livia Fulop, Exequiel E. Barrera, Ana M. Rodriguez, Luciana Mendez, Carina M. L. Depiccolo, Ernesto G. Mata, Federica Cioffi, Kerensa Broersen, Gabor Paragi, Ricardo D. Enriz
BIOORGANIC CHEMISTRY
(2018)
Article
Chemistry, Organic
Martin J. Riveira, Nadia L. Martiren, Mirta P. Mischne
JOURNAL OF ORGANIC CHEMISTRY
(2019)
Article
Plant Sciences
Martin J. Riveira
JOURNAL OF NATURAL PRODUCTS
(2020)
Article
Chemistry, Multidisciplinary
Melina G. Di Liberto, Agustin J. Caldo, Ariel D. Quiroga, Martin J. Riveira, Marcos G. Derita
Article
Chemistry, Medicinal
Nadia L. Martiren, Yanina Bellizzi, Elizabeth Barrionuevo, Viviana C. Blank, Leonor P. Roguin, Ernesto G. Mata, Patricia G. Cornier
Summary: This study synthesized and evaluated a library of peptoid analogs, with peptoid 4e showing the highest antiproliferative activity among the tested compounds, indicating its potential as a promising antitumor drug candidate.
FUTURE MEDICINAL CHEMISTRY
(2021)
Article
Chemistry, Organic
Aabid H. Bhat, Gaston N. Quiroga, Agustina La-Venia, Huck K. Grover, Martin J. Riveira
Summary: The study developed a simple method to access citridone A and related synthetic compounds, highlighting the power of domino cascades in the synthesis of natural product frameworks. This may help promote future studies on this promising new class of pyridone alkaloids.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Biochemistry & Molecular Biology
Yanina Bellizzi, Juan Manuel Anselmi Relats, Patricia G. Cornier, Carina M. L. Delpiccolo, Ernesto G. Mata, Florencia Cayrol, Graciela A. Cremaschi, Viviana C. Blank, Leonor P. Roguin
Summary: TAP7f induces apoptotic cell death in melanoma cells by inducing ER stress and activating p38, JNK, and PI3K-I/Akt pathways.
Review
Chemistry, Organic
Patricia G. Cornier, Carina M. L. Delpiccolo, Nadia L. Martiren, Ernesto G. Mata, Luciana Mendez, Caterina Permingeat Squizatto, Marianela G. Pizzio
Summary: Transition metal-catalyzed solid-phase reactions play an important role in synthetic biology and serve as a practical and fast strategy to meet the demands of organic chemistry.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Oncology
Yanina Bellizzi, Patricia G. Cornier, Carina M. L. Delpiccolo, Ernesto G. Mata, Viviana Blank, Leonor P. Roguin
Summary: The combination of TAP7f and thapsigargin has a synergistic antitumor effect on melanoma cells by inhibiting proliferation, inducing apoptosis and ER stress. In a mouse model, the combination therapy significantly reduced tumor volume without causing tissue toxicity.
JOURNAL OF CANCER RESEARCH AND CLINICAL ONCOLOGY
(2022)
Article
Chemistry, Organic
Agustina La-Venia, Lucas Passaglia, Lucia Gurgone, Vincent Gandon, Martin J. Riveira
Summary: This article presents a synthetic strategy for constructing 2-cyclopentenones through acid-promoted cyclization of all-trans linearly conjugated dienones and dienals.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Cristian M. Camacho, Marianela G. Pizzio, David L. Roces, Dora B. Boggian, Ernesto G. Mata, Yanina Bellizzi, Elizabeth Barrionuevo, Viviana C. Blank, Leonor P. Roguin
Summary: The development of hybrid compounds has led to the discovery of promising pharmacologically active agents for serious diseases such as cancer. A new series of oxadiazole-containing structures were designed through molecular hybridization, showing high cytotoxic selectivity in cytotoxicity assays.
Article
Chemistry, Organic
Maitena Martinez-Amezaga, Rocio A. Giordano, Denis N. Prada Gori, Caterina Permingeat Squizatto, Maria Giolito, O. Graciela Scharovsky, Viviana R. Rozados, Maria J. Rico, Ernesto G. Mata, Carina M. L. Delpiccolo
ORGANIC & BIOMOLECULAR CHEMISTRY
(2020)