Article
Biochemistry & Molecular Biology
Igor Yu Grishin, Nikolai A. Arutiunov, Dmitrii A. Aksenov, Nicolai A. Aksenov, Alexander Aksenov, Amina Z. Gasanova, Elena A. Sorokina, Carolyn Lower, Michael Rubin
Summary: In this study, polyphosphoric acid was used as a catalyst to efficiently synthesize 3-(1H-indol-3-yl)benzofuran-2(3H)-ones via condensation reaction between 3-(2-nitrovinyl)-1H-indoles and phenols.
Article
Biochemistry & Molecular Biology
Nicolai A. Aksenov, Alexander V. Aksenov, Igor A. Kurenkov, Nikita K. Kirillov, Dmitrii A. Aksenov, Nikolai A. Arutiunov, Daria S. Aksenova, Michael Rubin
Summary: A highly efficient one-pot method for the synthesis of biologically active 2-(3-oxoindolin-2-yl)acetonitriles has been designed, which involves a base-assisted aldol reaction followed by hydrocyanation, triggering an unusual reductive cyclization reaction.
Article
Chemistry, Organic
Suvendu Halder, Rupa Bai Addanki, Pavan K. Kancharla
Summary: The alkene-based o-[1-(p-MeO-phenyl)vinyl]benzoates (PMPVB) donors have been successfully used for the regio- and stereoselective synthesis of C-linked indolyl glycosides under catalytic Bronsted acidic conditions. The highly reactive glycosyl donors enable the use of poorly nucleophilic N-Boc and N-acetyl indole derivatives, resulting in excellent yields and stereoselectivities of the indolyl glycosides. Furthermore, conditions for recycling the byproduct have been developed, significantly improving the potential of these donors.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Applied
Hongmei Zhu, Lei Chen, Rongxian Bai, Yanlong Gu
Summary: Two classes of indole-tetrahydropyridine hybrid molecules were synthesized via three-component reactions, providing a straightforward approach for accessing diverse molecular structures. The reactions were likely triggered by Michael addition, leading to the formation of indol-3-ylimine intermediate, which was then trapped by the indole component. The resulting indol-3-yl-substituted tetrahydropyridines could be converted into indole-pyridine hybrid molecules with the aid of DDQ.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Ferdinand Taenzler, Jiasu Xu, Sudhakar Athe, Viresh H. Rawal
Summary: This article presents the dearomative (4 + 3) cycloaddition reactions of 3-alkenylindoles with in situ-generated oxyallyl cations, as well as the transformation of the resulting cycloadducts and preliminary investigations into their enantioselective catalysis using imidodiphosphorimidate catalysts.
Article
Chemistry, Multidisciplinary
Christopher B. Watson, Adrianna Kuechle, David E. Bergbreiter
Summary: Homogeneous and heterogeneous sulfonic acid catalysts are commonly used in organic chemistry, but this study explores the use of recyclable polymeric solvent and soluble catalysts which show excellent recyclability in organic synthesis. The non-volatile solvent system and phase-anchored catalysts demonstrated effectiveness in esterifications, acetalizations, and multicomponent condensations, allowing for efficient product separation and recycling through distillation or self-separation.
Article
Chemistry, Organic
Yunlong Zhao, Rou Xiao, Weibin Fang, Junling Zhao
Summary: This study presents a protocol for the highly selective addition reaction of isatin-derived beta,gamma-unsaturated alpha-ketoesters with 4-aminoindoles at the C7 position. The reaction, catalyzed by a SPINOL-derived chiral phosphoric acid, yields bisindole derivatives with up to 97% enantiomeric excess. Further biological testing revealed that the products have high cytotoxicity against various cancer cell lines.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Zijie Zhou, Ling Ye, Lu Yang, Xinying Li, Zhigang Zhao, Xuefeng Li
Summary: A three-component Povarov reaction has been developed for enantioselective construction of pyrroloquinolines with the presence of a chiral phosphoric acid. This reaction provides structurally important pyrroloquinolines as a single diastereomer in high yields and enantiomeric excess. It offers a concise approach to access enantioenriched pyrroloquinolines and enables regiospecific construction of three types of annulated cycles in the carbocyclic ring of indole.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Multidisciplinary
Biquan Xiong, Lulu Si, Yu Liu, Weifeng Xu, Tao Jiang, Fan Cao, Ke-Wen Tang, Wai-Yeung Wong
Summary: An efficient, cheap and green protocol has been established for the highly regioselective 1,6-hydroarylation of para-quinone methides (p-QMs) with indoles at the C-3 position using phosphoric acid catalysis in water under transition-metal-free reaction conditions. A wide range of indole derivatives and p-QMs are compatible, providing good to excellent yields of the corresponding 1,6-hydroarylation products. The possible mechanism of the reaction has been explored through step-by-step control experiments, making this protocol a convenient, safe, green and feasible way for the formation of C-3 diarylmethyl functionalized indole derivatives.
CHEMISTRY-AN ASIAN JOURNAL
(2022)
Article
Chemistry, Organic
Ke-Wei Chen, Dan-Dan Wang, Si-Jia Liu, Xue Wang, Yu-Chen Zhang, Yi-Ming Tian, Qiong Wu, Feng Shi
Summary: The study focuses on the catalytic asymmetric dearomative cycloaddition of 3-alkyl-2-vinylindoles using chiral phosphoric acid, resulting in the synthesis of chiral pyrroloindolines with two tetrasubstituted stereogenic centers in good yields and excellent stereoselectivities. This reaction introduces new reactivity to 3-alkyl-2-vinylindoles and presents a potential strategy for discovering anti-cancer drug candidates.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Applied
Ling Pan, Baihui Zheng, Xiaohui Yang, Liping Deng, Yifei Li, Qun Liu
Summary: A synthetic strategy for the synthesis of substituted thiophenes involves a one-pot reaction of indoles with ketene dithioacetals under mild conditions. The reaction, promoted by triflic acid (TfOH), leads to the formation of vinylketene dithioacetals instead of the usual nucleophilic addition-alkylthio elimination process. In the presence of CuBr2, the vinylketene dithioacetals cyclize to form substituted thiophenes, benefiting from the acidic reaction conditions and steric effects of the 2-substituted indoles.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Physical
Savarimuthu Selvan Clinton, Rengan Ramesh, Jan Grzegorz Malecki
Summary: The catalytic application of new orthometallated palladium(II) C-S pincer complexes has been reported for the synthesis of bis(indolyl)methanes using alcohols as feedstocks. The complexes were synthesized using [PdCl2(PPh3)(2)] and thiourea ligand derivatives, and characterized using various techniques. The complexes showed excellent catalytic activity and tolerance towards a wide range of substrates, resulting in high yields of bis(indolyl)methanes. The protocol also demonstrated the synthesis of biologically important compounds. Rating: 9 out of 10.
CATALYSIS SCIENCE & TECHNOLOGY
(2023)
Article
Chemistry, Multidisciplinary
Jordan P. Liles, Caroline Rouget-Virbel, Julie L. H. Wahlman, Rene Rahimoff, Jennifer M. Crawford, Abby Medlin, Veronica S. O'Connor, Junqi Li, Vladislav A. Roytman, F. Dean Toste, Matthew S. Sigman
Summary: Researchers developed a novel phosphoric acid catalyst with a minimalistic backbone that incorporates only a single instance of point chirality. Data science techniques were used to identify key features of the catalyst and develop a simple model for predicting selectivity. This approach was successfully applied to two other reaction transformations.
Article
Chemistry, Organic
Zhengyu Han, Wenlong Wang, Han Zhuang, Jie Wang, Cheng Wang, Jianhao Wang, Hai Huang, Jianwei Sun
Summary: This article describes an organocatalytic enantioselective formal hydro-arylation of 2-vinyl indoles for the synthesis of enantioenriched 2,3'-bis(indolyl)methanes bearing a quaternary carbon stereocenter. The reaction conditions are mild, the catalyst loading is low, and the efficiency and enantioselectivity are excellent. The resulting products exhibit promising anticancer activity.
Article
Chemistry, Organic
Alemayehu Gashaw Woldegiorgis, Zhao Han, Xufeng Lin
Summary: In this study, we developed a novel tandem reaction for the synthesis of pyrazolo[3,4-b]pyridin-6-ones bearing a -CF3 unit using chiral phosphoric acid and MgSO4 as catalysts. The reaction showed moderate to high yields, enantioselectivities, and diastereoselectivities, resulting in trifluoromethylated pyrazolo[3,4-b]pyridin-6-ones with two adjacent tertiary stereocenters.
Article
Chemistry, Organic
Dilek Isik Tasgin, Irem Bayraktar
Summary: We present a synthetic method for pyrrolizine-3-one derivatives and investigate their photophysical properties. These compounds are prepared through a series of reactions involving substituted pyrroles in one-pot, two-step oxidation, and intramolecular cyclization processes. The photophysical properties of the synthesized compounds are studied using UV-Vis and fluorescence spectroscopy in various solvents. The introduction of pyrrolyl substituents has a significant impact on Stokes shifts and quantum yield values.
SYNTHETIC COMMUNICATIONS
(2024)
Article
Chemistry, Organic
Satish Kumar Burra, Vaikunta Rao Lakinani, Raghunadh Akula, Chiranjeevi Yankkanti
Summary: A novel and green strategy for the construction of biologically relevant substituted indolyl-4H-chromenes scaffolds is reported, using L-proline as a catalyst and water as a promoter solvent. This catalytic system offers wider applicability, shorter reaction times, and high yields, making it an ideal condition for green chemistry.
SYNTHETIC COMMUNICATIONS
(2024)
Review
Chemistry, Organic
Abouelhaoul El Alami, Amine El Maraghi, Fatima Youssoufi, Assiya Atif, Hamid Sdassi
Summary: Nitrobenzimidazoles have become increasingly important in the design of new compounds in medicinal, therapeutic and chemical fields. This review provides an overview of the synthesis strategies and biological activities of nitrobenzimidazole derivatives.
SYNTHETIC COMMUNICATIONS
(2024)
Article
Chemistry, Organic
Nilesh Raghunath Khedkar, Alex Joseph, Milind Sindkhedkar
Summary: In this study, a new library of 3-(2-(pyrimidin-5-yl)thiazol-4-yl)-1,2,4-oxadiazole compounds was designed and synthesized as potential anticancer agents using in silico fragment-based drug design. The compounds were tested for their anticancer activity in vitro, and one compound exhibited excellent activity against multiple cancer cell lines.
SYNTHETIC COMMUNICATIONS
(2024)
Article
Chemistry, Organic
Terungwa H. Iorkula, Bryce A. Tolman, Scott R. Burt, Matt A. Peterson
Summary: A new method for synthesizing C-6 substituted products has been discovered in this study, which utilizes lower doses of fluoride and CsF as a catalyst, with high reaction yields and cost-effectiveness under suitable conditions.
SYNTHETIC COMMUNICATIONS
(2024)
Review
Chemistry, Organic
Ranjana Aggarwal, Swati Sharma
Summary: This review article mainly focuses on the synthesis of 3(5)-trifluoromethylpyrazoles via condensation reaction of trifluoromethyl-beta-diketones with hydrazines. It emphasizes the importance of fluorine-containing compounds and pyrazoles in the field of biology. The literature reported condensation reactions of trifluoromethyl-beta-diketones with hydrazines are covered.
SYNTHETIC COMMUNICATIONS
(2024)
Article
Chemistry, Organic
F. M. Alshareef, Sami A. Al-Harbi, Esam S. Allehyani, Omeima Abdullah, Magdy A. Ibrahim
Summary: This study aimed to construct a novel category of linear annulated chromeno[3',2':5,6]pyrido[2,3-d][1,3]thiazolo[3,2-a]pyrimidines. The chemical reactivity of the synthesized compounds was investigated, and they showed significant antimicrobial activity against various strains.
SYNTHETIC COMMUNICATIONS
(2024)
Article
Chemistry, Organic
Preethi Dhanapal, S. L. Manju
Summary: Thiazole based Schiff base scaffolds have become an integral part of drug development in recent years, playing a versatile role as building blocks for lead drug molecules. This study presents a facile one pot synthetic method for producing novel 4-aryl thiazoles with high yield, shorter reaction time, and milder conditions, without the need for catalysts or purification techniques.
SYNTHETIC COMMUNICATIONS
(2024)