Article
Chemistry, Multidisciplinary
Yi-Min Fan, Madison J. Sowden, Nicholas L. Magann, Erik J. Lindeboom, Michael G. Gardiner, Michael S. Sherburn
Summary: The first general synthesis of branched tetraenes ([4]dendralenes) and other related compounds has been achieved using a novel reaction method, with control over the stereoselectivity of the products. The broad applicability of this method opens up new opportunities for target-oriented synthesis.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2022)
Article
Chemistry, Physical
Anastasia Bobrova, Pavel O. Krasnov, Ilya G. Povarov, Pavel S. Bobrov, Aleksey Lyubyashkin, Georgiy A. Suboch, Mikhail S. Tovbis
Summary: This study describes the synthesis of alkyl- and naphthyl-substituted 4-aminopyrazoles by mild reduction of nitrosopyrazoles with high yields. Sulfonamide derivatives were obtained based on these 4-aminopyrazoles, and the structures of 15 synthesized previously unknown compounds were confirmed. Quantum-chemical calculations were used to determine the spatial structure of their most stable conformers.
JOURNAL OF MOLECULAR STRUCTURE
(2021)
Article
Chemistry, Organic
Anasheh Sookezian, Gary A. Molander
Summary: Alkyl sulfonamides are important bioactive molecules. Traditional syntheses usually require multiple steps and harsh reaction conditions. Photochemical methods have been limited in terms of the number of substituents that can be introduced onto an olefin. However, a new radical/polar crossover (RPC) method is introduced in this study, which allows for the first multicomponent 1,2-difunctionalization reaction with a sulfonamide moiety and a second reaction partner. This protocol, demonstrated on various olefins, employs different commercial sulfamoyl chlorides and organotrifluoroborates as coupling partners.
Article
Chemistry, Organic
Xiao Yu, Wenjing Zhu, Hongyan Liu, Yi Liu, Hongshuang Li, Junfen Han, Guiyun Duan, Zhushuang Bai, Pengfei Zhang, Chengcai Xia
Summary: A novel route involving metal-promoted tandem nitration and halogenation has been developed for the synthesis of N-(4-halo-2-nitrophenyl)benzenesulfonamide derivatives. The method shows high practicality, chemoselectivity, and compatibility with various functional groups. In addition, it uses insensitive and inexpensive nitration reagents and provides a direct approach for the preparation of 4-halo-2-nitroaniline, a crucial intermediate for the synthesis of benzimidazoles and quinoxaline derivatives.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Biochemistry & Molecular Biology
Milan Kumar Mandal, Swagatika Ghosh, Lieve Naesens, Hans Raj Bhat, Udaya Pratap Singh
Summary: The study involved the synthesis of novel compounds with significant antimicrobial and antiviral activities, particularly showing strong inhibitory effects against bacteria and fungi, as well as considerable antiviral activity against various viruses. The findings suggest potential for the development of compounds with dual antimicrobial and antiviral properties.
BIOORGANIC CHEMISTRY
(2021)
Article
Chemistry, Physical
Philip R. D. Murray, Isabelle Nathalie-Marie Leibler, Sandrine M. Hell, Eris Villalona, Abigail G. Doyle, Robert R. Knowles
Summary: We introduce a two-component annulation strategy that involves the combination of aryl alkenes and redox-active radical precursors bearing tethered nucleophiles, enabling the synthesis of a diverse collection of five- and six-membered saturated heterocycles. This strategy employs an Ir(III) photocatalyst and a Bronsted acid under visible-light irradiation. The synthesis involves reductive proton-coupled electron transfer, radical addition to alkene, oxidative radical-polar crossover, and cyclization of the tethered nucleophile. This approach allows the easy access to a wide range of heterocycles, including pyrrolidines, piperidines, tetrahydrofurans, morpholines, delta-valerolactones, and dioxanones. It is amenable to gram-scale preparation and complex fragment coupling.
Article
Chemistry, Organic
Yan Zhang, Bingxu Han, Xin Gu, Kaixuan Wang, Shuai Liang
Summary: A radical sulfonation-ipso-cyclization cascade promoted by Mn(OAc)(3).2H(2)O using functionalized alkynes or alkenes and potassium metabisulfite (K2S2O5) was reported. 30 spirocyclic sulfonates were synthesized under mild conditions. A modular synthesis approach was demonstrated for the preparation of various azaspiro[4,5]-trienone-based sulfonamides and sulfonate esters.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Peng Zhang, Caiqin Liu, Ling Yu, Huiqing Hou, Weiming Sun, Fang Ke
Summary: An environmentally friendly and efficient protocol for the synthesis of benzimidazoles using mortar-pestle grinding technique in the presence of acetic acid as a catalyst is reported. The mechanochemical method involves the condensation of aldehyde and o-phenylenediamine followed by cyclization reaction, leading to high yields up to 97%. This protocol is also applicable for the synthesis of benzothiazoles and benzoxazoles.
GREEN CHEMISTRY LETTERS AND REVIEWS
(2021)
Article
Chemistry, Multidisciplinary
Kevin M. Hoang, Nicholas R. Lees, Seth B. Herzon
Summary: A strategy for the synthesis of alpha- or beta-2,3,6-trideoxy-3-amino and 2,4,6-trideoxy-4-amino O-glycosides from a common precursor has been presented. This strategy involves reductive lithiation of thiophenyl glycoside donors and trapping of the resulting anomeric anions with 2-methyltetrahydropyranyl peroxides, providing high yields and selectivities for the desired products. Furthermore, donors with axial amine substituents favored beta-products at low temperatures, establishing a general strategy for synthesizing O-glycosides bearing basic nitrogen.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Khuong Quoc Vo, Man Van Tran, Thu Anh Nguyen, Anh-Thi Tran Cao, Sy Van Vu, Kha Ni Tran, Nguyen Thanh Si, Vu-Nhat Pham
Summary: In this study, a nanosubstrate for trace determination of sulfathiazole (STZ) was prepared using surface-enhanced Raman scattering (SERS) technique. The nanosubstrate, composed of spinous gold nanoparticles (SGNPs) with long tips, showed high sensitivity and good reproducibility. It could detect STZ at low concentrations and had an excellent linear correlation between concentration and intensity. The nanosubstrate has potential applications in measuring various antibiotics.
NEW JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Organic
Chen Li, Yilei Huang, Sheng Cao, Yunhao Luo, Ying Zhang, Guang Yang
Summary: The study demonstrates a robust and facile method for desulfonation to achieve secondary amines, using diphenylphosphine as a catalyst. Aromatic and aliphatic sulfonamides were cleanly converted to the required amines with good to excellent chemical yields in a rapid reaction time. The functional groups tested were generally well tolerated.
ORGANIC CHEMISTRY FRONTIERS
(2021)
Article
Chemistry, Organic
Michal Tryniszewski, Dariusz Basiak, Michal Barbasiewicz
Summary: Methanedisulfonyl fluoride can convert aromatic aldehydes into useful substrates and mimic the mechanism of Horner-Wadsworth-Emmons olefination. In the absence of base, electron-rich aldehydes can also undergo Knoevenagel condensation to yield unsaturated 1,1-disulfonyl fluorides. Additionally, elusive ethene-1,1-disulfonyl fluoride can be trapped with 4-(dimethylamino)pyridine to form a zwitterionic adduct as characterized by X-ray studies.
Article
Materials Science, Biomaterials
Veronika Riedl, Matthias Portius, Lara Heiser, Philipp Riedl, Torsten Jakob, Rosa Gehring, Thorsten Berg, Tilo Pompe
Summary: Sulfonamides were the first synthetic antibiotics widely used in veterinary and human medicine. Their accumulation in the environment due to increased usage and limited degradation technology after entering the sewage system has raised concerns. A new hydrogel microparticle based biosensing application for sulfonamides has been developed to provide a less labor-intensive and expensive detection method for analyzing their environmental distribution. The microparticles were successfully functionalized with sulfamethoxazole (SMX) derivatives, which can be used for sulfonamide detection, pull-down assays, and screenings for new binding targets.
JOURNAL OF MATERIALS CHEMISTRY B
(2023)
Article
Chemistry, Multidisciplinary
Zhongzhen Yang, Illya Zalessky, Ryan G. Epton, Adrian C. Whitwood, Jason M. Lynam, William P. Unsworth
Summary: Two new strategies for synthesizing medium sized ring and macrocyclic sulfonamides are reported. These methods do not require classical protecting groups and involve nitro reduction and amine conjugate addition respectively for ring expansion. Both methods yield diversely functionalized cyclic sulfonamides in good to excellent yields, and the ring size dependency matches with Density Functional Theory calculations.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Multidisciplinary Sciences
Ye-Chuang Han, Meng-Li Liu, Li Sun, Shuxing Li, Gen Li, Wei-Shen Song, Yan-Jie Wang, Zi-Ang Nan, Song-Yuan Ding, Hong-Gang Liao, Yonggang Yao, Galen D. Stucky, Feng Ru Fan, Zhong-Qun Tian
Summary: In this study, a low-pressure carbothermal reduction (CR) strategy was proposed and demonstrated for the synthesis of high-surface area silicon carbide (SiC) at a lower temperature. The feasibility of this method for the synthesis of other refractory carbides and high-entropy carbides was also shown.
PROCEEDINGS OF THE NATIONAL ACADEMY OF SCIENCES OF THE UNITED STATES OF AMERICA
(2022)
Article
Chemistry, Organic
Geeta Devi Yadav, Pooja Chaudhary, Balaram Pani, Surendra Singh
Summary: Chiral transition metal complexes with privileged ligands are efficient catalysts for various asymmetric organic transformations. Transition metal complexes of C1-symmetric pyrrolidine-based ligands have been widely used in asymmetric organic reactions. However, a comprehensive review article on the transition metal complexes of chiral C1-symmetric pyrrolidine-based ligands derived from (L)-proline has not been published.
TETRAHEDRON LETTERS
(2024)
