Article
Chemistry, Organic
Leonie O'Sullivan, Ketul V. Patel, Ben C. Rowley, Duncan K. Brownsey, Evgueni Gorobets, Benjamin S. Gelfand, Jeffrey F. Van Humbeck, Darren J. Derksen
Summary: A regioselective route to C3-hydroxyarylated pyrazoles was developed using mild conditions, allowing for the synthesis of a JAK 1/2 inhibitor in just 4 steps from commercially available starting materials.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Biqiong Hong, Xinzhi Ding, Mengfan Jiang, Lu Qin, Zitong Lin, Wei Wu, Zhiqiang Weng
Summary: An efficient and general method for the synthesis of 3-trifluoromethyl-4 trifluoroacetyl pyrazoles from the cycloaddition of sydnones with 1,1,1,5,5,5-hexafluoropentane-2,4-dione has been established. The protocol using ZnI2/bpy as a catalyst in THF proved to be general and resulted in good yields of various 3-trifluoromethyl-4 trifluoroacetyll pyrazoles. Moreover, the trifluoroacetyl moiety can be further transformed to obtain convenient access to 3-trifluoromethyl pyrazole-based carboxylic acid and alcohol derivatives.
TETRAHEDRON LETTERS
(2022)
Article
Chemistry, Applied
Yu-Chen Tian, Jun-Kuan Li, Fa-Guang Zhang, Jun-An Ma
Summary: 1,4-Diaryl-5-carboxamido substituted 3-trifluoromethylpyrazoles are obtained with exclusive regioselectivity under transition-metal-free conditions using trifluoromethyl nitrilimines and isoxazolidinediones. This method is also compatible with various nitrilimines and can be used to prepare analogues of the drug Celebrex.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Multidisciplinary
Manon Louis, Guillaume Force, Timothee D'Anfray, Emma Bourgeat, Eugenie Romero, Pierre Thuery, Davide Audisio, Antoine Sallustrau, Frederic Taran
Summary: This study investigated the reactivity of sydnones and sydnonimines toward terminal alkynes under copper catalysis using High-Throughput-Experimentation. By screening a large panel of ligands and reaction conditions, new ligands were discovered, enhancing the catalytic properties of copper and leading to the discovery of a new click-and-release reaction.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Yin Zhou, Cheng-Feng Gao, Hai Ma, Jing Nie, Jun-An Ma, Fa-Guang Zhang
Summary: This article presents a quadruple functionalization approach for the construction of fully substituted N-1-aryl 3-di/trifluoro-methyl-4/5-cyanopyrazole pharmacophores. The one-pot strategy offers access to a diverse library of compounds, some of which have potent inhibitory activity against cyclooxygenase 2 (COX-2).
CHEMISTRY-AN ASIAN JOURNAL
(2022)
Article
Chemistry, Organic
Ke-Hu Wang, Haimei Liu, Xiaoling Liu, Chang Bian, Junjiao Wang, Yingpeng Su, Danfeng Huang, Yulai Hu
Summary: An efficient cycloaddition reaction was developed for the synthesis of 3-trifluoromethyl-4-substituted pyrazoles. The reaction exhibits mild conditions, good tolerance of functional groups, and simple operation.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Manon Louis, Alex Talbot, Diana Lamaa, Antoine Sallustrau, Davide Audisio, Frederic Taran
Summary: A new synthetic route to indazolo[2,3-a]quinoxaline derivatives is described, which involves the 1,3-dipolar cycloaddition of arynes to quinoxaline-sydnone derivatives as a key step, and the preparation of polyaromatic sydnones through a copper-promoted intramolecular cyclization of the C-4 position of sydnones on imines.
Article
Pharmacology & Pharmacy
Vincenzo Algieri, Cristina Algieri, Paola Costanzo, Giulia Fiorani, Antonio Jiritano, Fabrizio Olivito, Matteo Antonio Tallarida, Fabiana Trombetti, Loredana Maiuolo, Antonio De Nino, Salvatore Nesci
Summary: An efficient, eco-compatible, and inexpensive method for constructing fully substituted pyrazoles (Pzs) was developed via the eliminative nitrilimine-alkene 1,3-dipolar cycloaddition (ENAC) reaction. The reaction yielded high regioselectivity and excellent yield, with enaminones and nitrilimines as dipolarophiles and dipoles, respectively. The F1FO-ATPase activity and mitochondrial permeability transition pore (mPTP) opening were evaluated for three different structures of Pzs, showing reduced activity and concentration-dependent inhibitory effects.
Article
Chemistry, Inorganic & Nuclear
Shuo-Han Li, Ran Guo, Ning Lv, Yu Liu, Xiaodong Tang, Jun-An Ma
Summary: In this study, a metal-free and highly regioselective [3 + 2] cycloaddition reaction between diazo compounds and internal alkynes has been developed, leading to a series of trifluoromethylated pyrazoles. By using different combinations of starting materials, both regioisomers can be obtained under this protocol. The developed cycloaddition reaction provides a valuable tool for future medicinal chemistry research on highly substituted trifluoromethyl pyrazoles.
JOURNAL OF FLUORINE CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Martin Linden, Silja Hofmann, Antonia Herman, Nicole Ehler, Robin M. M. Baer, Siegfried R. R. Waldvogel
Summary: This study presents the first electrochemical approach for the direct synthesis of pyrazolines and pyrazoles from easily accessible hydrazones and dipolarophiles. The method allows for large-scale production and even conversion of highly sensitive alkenes. The use of a biphasic system with sodium iodide as a supporting electrolyte and mediator is cost-effective. Mechanistic insight is provided by the isolation of key intermediates, and the synthesis of a commercial herbicide safener further highlights the significance of this reaction.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Multidisciplinary
Song Cheng, Wen Gu, Kun Zhao, Shu Ting Zhang, Lan Yang, Qing Song Liu, Xiao Xiao Li, Zhi Gang Zhao
Summary: A strategy for synthesizing iodo-substituted allylic pyrazoles through NIS-mediated regioselective addition is presented. This reaction is fast, scalable, and tolerant of a wide range of substrates. Additionally, the products can undergo coupling reactions with phenylacetylene under Sonogashira cross-coupling conditions.
NEW JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Organic
Soumita Dwari, Partha Partim Nath, Chandan K. Jana
Summary: An unprecedented method for the synthesis of 1,3-diaryl 4-alkyl pyrazoles as a single regioisomer has been reported, which avoids the use of additional steps and hazardous oxidants.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Zhongfeng Luo, Chengjie Wang, Huanfeng Jiang, Wei Zeng
Summary: A Rh-catalyzed amine-directed cross-coupling of 2-aminopyridines with 1-sulfonyl-triazoles has been developed, providing an efficient approach to access 5-aminovinylpyridines with wide functional group tolerance.
Article
Chemistry, Multidisciplinary
Bhargava Sai Allaka, Srinivas Basavoju, Rama Krishna Gamidi
Summary: This study describes a highly efficient and regioselective synthesis method for the production of 3,4,5-trisubstituted pyrazoles. The method involves a transition metal- and oxidant-free, three component [3+2] cycloaddition reaction using thiazolidinedione chalcones, benzaldehydes, and N-tosylhydrazine as substrates. Under mild reaction conditions, C-C and C-N bond formations occur, leading to the formation of structurally diverse polysubstituted pyrazoles in moderate to good yields.
Article
Chemistry, Organic
Suvam Paul, Sourav Das, Tathagata Choudhuri, Papiya Sikdar, Avik Kumar Bagdi
Summary: A visible light-induced cross-dehydrogenative methodology has been developed for the regioselective sulfenylation of pyrazolo[1,5-a]pyrimidine derivatives. This protocol allows the synthesis of a library of 3-(aryl/heteroaryl thio)pyrazolo[1,5-a]pyrimidine derivatives with broad functionalities. The methodology also shows selectivity, scalability, and efficiency in sulfenylation of various substrates.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Andrew W. Brown, Joseph P. A. Harrity
JOURNAL OF ORGANIC CHEMISTRY
(2015)
Article
Chemistry, Medicinal
Andrew W. Brown, Matthew Fisher, Gillian M. Tozer, Chryso Kanthou, Joseph P. A. Harrity
JOURNAL OF MEDICINAL CHEMISTRY
(2016)
Article
Chemistry, Organic
Prisca Fricero, Laurent Bialy, Andrew W. Brown, Werngard Czechtizky, Maria Mendez, Joseph P. A. Harrity
JOURNAL OF ORGANIC CHEMISTRY
(2017)
Article
Chemistry, Medicinal
Andrew W. Brown, Toby Holmes, Matthew Fisher, Gillian M. Tozer, Joseph P. A. Harrity, Chryso Kanthou
Article
Multidisciplinary Sciences
Toby Holmes, Andrew W. Brown, Marie Suggitt, Lucy A. Shaw, Lucy Simpson, Joseph P. A. Harrity, Gillian M. Tozer, Chryso Kanthou
SCIENTIFIC REPORTS
(2020)
Article
Chemistry, Multidisciplinary
Andrew W. Brown, Julia Comas-Barcelo, Joseph P. A. Harrity
CHEMISTRY-A EUROPEAN JOURNAL
(2017)
Article
Chemistry, Organic
Fuying Zhu, Yamei Lin
Summary: In this study, a low-metal iron-supported catalyst (Fe20/NC-Mg) was reported for the efficient synthesis of quinoxaline compounds, using water as a solvent and without additional bases. The synergistic effect of FeNx site and Mg (OH)2 nanorods in the catalyst played a key role in achieving high yields (82-91%) in 16 examples. The gram-level synthesis and reusability of the catalysts after four cycles demonstrated its industrial application potential.
Article
Chemistry, Organic
Mikhail Kozlov, Alexey Tyurin, Andrey Dmitrenok, Vyacheslav Rusak, Aleksander Fedorov, Igor Zavarzin, Yulia Volkova
Summary: This study presents a novel and practical synthesis method for phosphorus-substituted 1,3,4-thiadiazolines using phosphorylthioformic acid hydrazides and ketones. The protocol demonstrates operational simplicity, availability of reagents, and tolerance towards different functional groups.
Article
Chemistry, Organic
Jisna Jose, Thomas Mathew
Summary: 2-Cyclopentenone and its derivatives are highly esteemed synthetic intermediates with exceptional utility in organic synthesis. They are favored structural motifs in numerous pharmaceutical drugs and natural products, highlighting their significance. The review discusses the various methods used to synthesize cyclopentenones from 2016 to 2023.
