Article
Chemistry, Multidisciplinary
Morten Suk, Stefanie Lorenz, Klaus Kuemmerer
Summary: Many micropollutants, including pharmaceuticals and other chemicals, are found worldwide in aquatic environments. Transformations during effluent treatment and in the environment can lead to the formation of new chemicals with unknown structure, fate, and toxicity. Designing chemicals that can be fully mineralized or broken down into non-hazardous fragments is considered a green chemistry approach to prevent these issues from the beginning. This study focused on investigating the biodegradability of various N-heterocycles to identify environmentally friendly lead scaffolds, and found that only a small portion of the tested substances were readily biodegradable.
SUSTAINABLE CHEMISTRY AND PHARMACY
(2023)
Article
Chemistry, Applied
Tsai-Hui Lung, Yi-Ru Chen, Chen-Ling Chang, Wey-Chyng Jeng, Pei-Shan Wu, Sandip Sambhaji Vagh, Gangababu Marri, Yi-Fang Lin, Wenwei Lin
Summary: A catalyst-controlled diversity-oriented synthesis of spirohydroquinoline-indandiones and 3-methylenehydroquinoline-indandiones was reported using ortho-sulfonamidophenyl-substituted para-quinone methides and allylidene-indandiones. Organobases such as DMAP or TMG were utilized to selectively control the reaction pathway, resulting in products with yields of 40-99% and excellent diastereoselectivities. Mechanistic studies revealed that spirohydroquinoline-indandione was the kinetic product, which underwent an unusual base-initiated 1,3-nitrogen rearrangement process to afford 3-methylenehydroquinoline-indandione in the presence of TMG.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Jing-Hong Guo, Yu Liu, Xin-Cheng Lin, Tian-Mu Tang, Bi-Qin Wang, Ping Hu, Ke-Qing Zhao, Feijie Song, Zhang-Jie Shi
Summary: In this study, an unprecedented highly selective cleavage of C1-C8 bond with the insertion of alkynes was achieved by using a blocking strategy via Ni catalysis. This provides an efficient method for the synthesis of 1,8-disubstituted naphthalenes, with the potential for easy removal of the blocking group after the transformation.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Applied
Xiaoting Gu, Xiaoxiang Zhang, Wenhua Yu, Ke Sun, Wanxing Wei, Zhuan Zhang, Taoyuan Liang
Summary: This study presents a directing-group-free, three-component tandem C3-acylation/C5,6-H disulfenylation method for the position-selective functionalization of the poorly reactive benzenoid nucleus of indoles. The protocol demonstrates exceptional regio- and chemo-selectivity, broad substrate scope, good functional group tolerance, and mild reaction conditions. Importantly, this method offers great potential for the development of general site-selective functionalization at the benzenoid nucleus of indoles without the requirement for neighboring activating groups.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Yawei Tian, Yaping Shang, Weiping Su
Summary: This method utilizes a vinylogous strategy to form dienolate intermediates, providing a new approach for the regioselective alpha-alkylation of enones. It demonstrates a broad substrate scope and good functional group compatibility, allowing for the formation of unexpected cyclic 1,5-diketone with all-carbon quaternary centers at gamma-position of enones.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Multidisciplinary Sciences
Huamin Wang, Mingming Yu, Panyue Zhang, Hao Wan, Hengjiang Cong, Aiwen Lei
Summary: This study investigates a strategy for synthesizing α-chlorosulfoxides using electrochemistry, which offers a broad substrate scope, high selectivity, and regionality, and can be applied to the late-stage modification of amino acids and pharmaceutical derivatives.
Article
Chemistry, Physical
Yaqin Peng, Chenghua Gao, Zili Zhang, Shijie Wu, Jing Zhao, Aitao Li
Summary: This study presents a chemoenzymatic strategy for the synthesis of steroid drugs and successfully achieves regio- and stereoselective modifications with high yields. It demonstrates great potential for industrial applications.
Article
Chemistry, Physical
Sagar Arepally, Ponnusamy Nandhakumar, Gisela A. Gonzalez-Montiel, Alina Dzhaparova, Gyeongho Kim, Ahyeon Ma, Ki Min Nam, Haesik Yang, Paul Ha-Yeon Cheong, Jin Kyoon Park
Summary: Electrochemical access to organometallic redox reagents allows for selective synthesis of various benzene derivatives with different regioisomers. A unified electrochemical strategy is presented for the selective cyclotrimerization of terminal alkynes to access both 1,3,5- and 1,2,4-regioisomeric trisubstituted benzene derivatives. The regiocontrol can be switched by the addition of a carboxylic acid.
Article
Chemistry, Organic
Akira Nakamura, Tohko Kine, Haruna Uenishi, Yuri Maki, Yasuhito Kase, Mayo Takagi, Tomohiro Maegawa
Summary: A regioselective synthesis of 3,4-disubstituted isoxazoles has been developed using a chalcone-rearrangement strategy. The reaction of beta-ketoacetals with hydroxylamine hydrochloride and pyridine resulted in the formation of the corresponding 3,4-disubstituted isoxazoles via isoxazolines or oximes. Depending on the substrate, another disubstituted isomer was also obtained under optimized conditions, and a reaction mechanism is proposed for each transformation.
Article
Chemistry, Organic
Subhash P. P. Chavan, Dinesh B. B. Kalbhor, Rajesh G. G. Gonnade
Summary: A concise and highly diastereoselective bioinspired key cationic cyclization strategy for the asymmetric synthesis of the tricyclic core of (-)-stemoamide has been developed. Precursors of key N-acyliminium ions were obtained from L-tartaric acid and L-malic acid. The use of ethyl acetoacetate derived bifunctional allylidenetriphenylphosphorane reagent in the early stage was advantageous for the rapid construction of highly functionalized pyrrolo[1,2-& alpha;]azepine frameworks.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Saira Banu, Shubham Choudhari, Girija Patel, Prem P. Yadav
Summary: The study presents a tandem photocatalytic approach using chlorophyll for the oxidative functionalization of indoles, showcasing its dual catalytic activity through photoinduced electron transfer and energy transfer. The highlight is the auto-tandem photocatalytic role of chlorophyll in enabling green oxidation reactions.
Article
Chemistry, Multidisciplinary
Taisei Amano, Hideki Inagaki, Yoshinori Shirakawa, Yuuki Yano, Yosuke Hisamatsu, Naoki Umezawa, Nobuki Kato, Tsunehiko Higuchi
Summary: Cytochrome P450 selectively hydroxylates specific positions of fatty acids. A new synthetic strategy involving the introduction of eight bulky aryl groups at the 2,6-positions of the meso-phenyl groups after construction of the porphyrin skeleton greatly improved catalyst yield, resulting in Ru complexes with higher turnover numbers and unique selectivity.
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN
(2021)
Article
Biochemistry & Molecular Biology
Hannah E. Carter, Baylee Wildman, Heidi A. Schwanz, Robert J. Kerns, Katie J. Aldred
Summary: Fluoroquinolones, an important class of antibacterials, are facing a threat to their clinical efficacy due to rising levels of resistance. Understanding the mechanism of action of these drugs against target enzymes could help in designing more effective quinolone-based drugs to overcome resistance. This study investigates the existence and function of the water-metal ion bridge in the Gram-negative gyrase, which has been found in other type II topoisomerases. Evidence suggests that this bridge does exist in quinolone interactions with the gyrase enzyme and plays a positioning role. Further studies will explore the universality of this bridge and its implications.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2023)
Article
Biochemistry & Molecular Biology
Yuly Lopez, Laura Munoz, Domingo Gargallo-Viola, Rafael Canton, Jordi Vila, Ilonka Zsolt
Summary: The study revealed that ozenoxacin demonstrated superior accumulation inside bacterial cells compared to other quinolone drugs, and showed higher inhibitory activity against DNA gyrase and topoisomerase IV isolated from Staphylococcus aureus.
INTERNATIONAL JOURNAL OF MOLECULAR SCIENCES
(2021)
Article
Chemistry, Organic
Peter Langer
Summary: This article presents a personalized approach to synthesizing nitrogen heterocycles by combining regioselective Pd-catalyzed cross-coupling reactions and acid-mediated cycloisomerization reactions. The resulting products exhibit new heterocyclic core structures and display interesting optical and electronic properties.
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.
