Article
Biochemistry & Molecular Biology
Manuel Velasco, Nancy Romero-Ceronio, Rosalia Torralba, Oswaldo Hernandez Abreu, Miguel A. Vilchis-Reyes, Erika Alarcon-Matus, Erika M. Ramos-Rivera, David M. Aparicio, Jacqueline Jimenez, Eric Aguilar Garcia, David Cruz Cruz, Clarisa Villegas Gomez, Cuauhtemoc Alvarado
Summary: The study presents a simple and efficient method for the synthesis of coumarin-3-carboxamides, using a metal-free and clean reaction system with low catalyst loading and no tedious workup.
Article
Chemistry, Applied
Jie Huo, Xiao Geng, Wanmei Li, Pengfei Zhang, Lei Wang
Summary: A photoinduced multicomponent reaction involving arylamines, enaminones, and difluorobromoacetates has been developed for the synthesis of 2,3-difunctionalized quinolines. This strategy demonstrates broad functional group tolerance and wide substrate scopes, allowing for further synthetic applications of the resulting products. Mechanistic studies have revealed that intermolecular [3+3] cyclization between in-situ generated 1,3-vinylimine ions and arylamines is the crucial step in this transformation.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Physical
Dipti B. Upadhyay, Ruturajsinh M. Vala, Subham G. Patel, Paras J. Patel, Celestine Chi, Hitendra M. Patel
Summary: Herein, an efficient synthesis of spiropyran[3,2-c]quinoline derivatives of spiroxindolines by the water-mediated three-component condensation reaction is described. The synthesized compounds showed good alpha-amylase inhibitory activity, with compounds 4g and 4h being the most active. Molecular docking results revealed key interactions of 4g, 4h, and acarbose with alpha-amylase. ADMET prediction was carried out to evaluate the physicochemical properties of the synthesized compounds.
JOURNAL OF MOLECULAR STRUCTURE
(2023)
Article
Chemistry, Organic
Dahan Wang, Li Zhang, Fuhong Xiao, Guojiang Mao, Guo-Jun Deng
Summary: An electrochemical method for achieving the C3-thiolation of quinoline compounds has been developed with maximum atom economy, direct conversion, and the use of simple and readily available starting materials. Various aryl/alkyl/heteroaryl thiols and even diselenides can undergo this transformation within the conditions of an undivided cell, providing C-S-bond-containing products in up to 84% yield. BF3 center dot OEt2 plays an irreplaceable role as an additive. Cyclic voltammetry and mechanistic studies suggest the interception of intermediates from the cathodic reduction of quinolines by thiols and disulfides.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Review
Chemistry, Organic
Walysson Ferreira de Paiva, Yuri de Freitas Rego, Angelo de Fatima, Sergio Antonio Fernandes
Summary: The multicomponent Povarov reaction is a powerful method for synthesizing substances with N-heterocyclic frameworks, capable of forming multiple new bonds.
SYNTHESIS-STUTTGART
(2022)
Article
Chemistry, Organic
Rong Zhang, Jun Wang, Weiwei Jin, Yonghong Zhang, Bin Wang, Yu Xia, Chenjiang Liu
Summary: An efficient iodine-catalyzed [3+3+1] annulation for constructing dihydrooxepine scaffolds with quinoline units was developed, expanding the substrate scope. Further derivatization of the target product produced a trioxabicycle scaffold, serving as the basic core of natural products and pharmaceutical molecules.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Applied
Ben-Jie Jiang, Song-Lin Zhang
Summary: A general method is developed for the synthesis of quinolines and C2-functionalized quinolines from ortho-alkenyl anilines using a difluorocarbene precursor. The method involves the in-situ generation of isocyanides from primary aniline and difluorocarbene, which then undergo alpha-addition by neighboring alkenyl groups to form the quinoline ring. In the presence of Se, selenoisocyanate intermediates are generated, leading to the synthesis of 2-SeH quinolines. The method allows for the modular synthesis of various C2-functionalized quinolines in one step, using readily available starting compounds.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Review
Biochemistry & Molecular Biology
Andrzej Danel, Ewa Gondek, Mateusz Kucharek, Pawel Szlachcic, Arkadiusz Gut
Summary: This paper summarizes over 100 years of research on the synthesis, photophysical and biological properties of 1H-pyrazolo[3,4-b]quinolines published from 1911 to 2021. The main synthesis methods, including Friedlander condensation, synthesis from anthranilic acid derivatives, multicomponent synthesis, and others, are described. The potential applications of this class of compounds as fluorescent sensors and biologically active compounds are demonstrated. This review aims to provide an overview of the aforementioned aspects in 1H-pyrazolo[3,4-b]quinoline chemistry, with some of the presented results originating from the authors' laboratories.
Article
Chemistry, Applied
Qiang Tang, Keke Xu, Xinwei He, Yongjia Shang
Summary: A metal-free cascade annulation strategy has been developed for the synthesis of polysubstituted imidazoles and 4-alkenylquinazolines. The reaction proceeds through sequential conjugate addition, annulation/aromatization, and nucleophilic addition/elimination/aromatization steps. The method shows broad substrate scope and high yields, as demonstrated by gram-scale experiments and synthetic transformations.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Masoumeh Mazloumi, Farhad Shirini
Summary: The synthesis of quinoline, quinazoline and spiro-quinazoline derivatives can be effectively promoted using nanoporous TiO(2) containing an ionic liquid bridge. This method allows for the production of high yields in very short reaction times under solvent-free conditions, and the catalyst can be reused.
POLYCYCLIC AROMATIC COMPOUNDS
(2022)
Article
Chemistry, Organic
Guang Chen, Xinyuan Cai, Xinying Zhang, Xuesen Fan
Summary: This paper presents a selective synthesis of indolo[1,2c]quinazolines and indolo[3,2-c]quinolines through cascade reactions. The approach involves the generation of a carbene species and its reaction with 2-(1H-indol-2-yl)aniline, followed by formation of a deoxygenative imine, intramolecular nucleophilic addition, and aromatization. The method provides a convenient access to polycyclic heteroaromatic compounds through direct C-H/N-H functionalization. The protocols offer advantages such as readily accessible substrates, tunable selectivity, good compatibility with diverse functional groups, and the use of air as a sustainable oxidant.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Ahmed M. El-Saghier, Mohamed El-Naggar, Abdel Haleem M. Hussein, Abu-Bakr A. El-Adasy, M. Olish, Aboubakr H. Abdelmonsef
Summary: A new series of quinoline derivatives were efficiently synthesized under solvent-free conditions with excellent yields. These compounds showed promising antioxidant and antibacterial activity, especially compound 9 which exhibited the highest negative binding energy and potential as future drug candidates for antioxidant and antibacterial agents.
FRONTIERS IN CHEMISTRY
(2021)
Article
Chemistry, Organic
Lan Bao, Yu Liu, Jinghan Peng, Yuan Wang, Jinhuan Dong, Xianxiu Xu
Summary: The catalyst-free chemoselective trimerization reaction of isocyanides leads to the formation of a wide range of 2-(indol-2-yl)-quinolines and 2-(indol-2-yl)-pyridines in moderate to excellent yields. The key step of this reaction is proposed to be the head to head heterodimerization of two isocyanides.
Article
Chemistry, Organic
Swadhin Chetia, Samprity Sarmah, Apurba Dutta, Diganta Sarma
Summary: A copper acetate monohydrate catalyzed protocol for the construction of quinazoline derivatives and quinolines analogues via dehydrogenative coupling of 2-aminoaryl methanols and nitriles is developed. The reaction proceeded in toluene at 110 degrees C for 5 h without the requirement of inert condition, external additives, and ligands.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Rahul Yadav, Darakshan, Prabhas Bhaumick, Lokman H. Choudhury, Tasneem Parvin
Summary: A new method for the synthesis of pentacyclic pyran fused pyrazolo benzo[h]quinolines was reported in this study, which involved a one-pot reaction in acetic acid medium. The method allowed the formation of new bonds and rings, resulting in the synthesis of bioactive compounds. The method has the advantages of one-pot process, short reaction time, easier purification, and good product yields.
Article
Chemistry, Organic
Alemayehu Gashaw Woldegiorgis, Zhao Han, Xufeng Lin
Summary: The highly regio-, diastereo-, and enantioselective dearomatization reaction of 1-substituted 2-naphthols and beta,gamma-alkynyl-alpha-imino esters with complete atom economy is disclosed via chiral phosphoric acid catalysis. This protocol provides facile and efficient access to asymmetric construction of axially chiral allene-derived naphthalenones bearing quaternary stereocenters in good yields with high diastereoselectivities and enantioselectivities.
Article
Chemistry, Organic
Zhouli Chen, Lei Wang, Yiheng Qian, Xufeng Lin
Summary: An asymmetric [4+3]-cyclization reaction catalyzed by chiral phosphoric acids has been developed, providing efficient access to biologically important compounds with both axial and central chirality in good yields and up to 98% ee, as essentially single diastereomers under mild reaction conditions.
Review
Chemistry, Physical
Zhenjun Mao, Haorui Gu, Xufeng Lin
Summary: Pd/C-catalyzed reactions, including reduction reactions and cross-coupling reactions, are essential in modern organic synthesis. The heterogeneous Pd/C catalyst system offers unique advantages and applications compared to homogeneous systems, and this review covers advances in Pd/C-catalyzed methodologies and its use in total synthesis.
Article
Chemistry, Applied
Alemayehu Gashaw Woldegiorgis, Zhao Han, Xufeng Lin
Summary: An enantioselective synthesis of unnatural pyrazole-based alpha-chiral amino acid derivatives was developed using a chiral spirocyclic phosphoric acid catalyst, with yields ranging from 67-98% and enantioselectivities of 73-99%. The NH2 functionality in the products enables further transformations to a chiral thiourea and a lactam, providing a versatile synthetic route for obtaining tetrasubstituted carbon stereocenters in pyrazole-based alpha-amino acid derivatives.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Review
Chemistry, Organic
Alemayehu Gashaw Woldegiorgis, Xufeng Lin
Summary: This review summarizes the recent advances in the chiral phosphoric acid-catalyzed synthesis of a wide range of axially chiral compounds with high efficiency and excellent stereoselectivity, including biaryls, heterobiaryls, vinylarenes, N-arylamines, spiranes, and allenes.
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Physical
Dandan Hu, Jun-Qi Zhang, Xiang Wang, Jinyu Song, Xufeng Lin, Hongjun Ren
Summary: This study presents a one-pot solvothermal method for synthesizing diverse bimetallic organic frameworks. Among them, the material [NiFe(tda)(H2O)]n with a unique morphology shows outstanding electrocatalytic performance for oxygen evolution reaction.
JOURNAL OF POWER SOURCES
(2022)
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.
Review
Chemistry, Organic
Alemayehu Gashaw Woldegiorgis, Muhammad Suleman, Xufeng Lin
Summary: Asymmetric cycloaddition/annulation reactions have played a significant role in the synthesis of novel cyclic compounds for organic synthesis, natural product synthesis, material science, and chemical biology. Chiral phosphoric acid-catalyzed reactions have attracted attention in the synthetic community for the past two decades to develop new asymmetric reactions and synthesize complex molecules.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Linxi Yao, Alemayehu Gashaw Woldegiorgis, Shaoying Huang, Yongtao Wang, Xufeng Lin
Summary: We report a highly enantioselective desymmetrization reaction for the synthesis of axially chiral biaryl N-oxides by atroposelective C-H iodination using a chiral catalyst coordinated by N-benzoyl-l-phenylalanine. A broad range of products were obtained in high yields (up to 99%) with excellent enantioselectivities (up to 98% ee). The products could be synthesized in gram scale, and one of them was shown to be a powerful organocatalyst in asymmetric allylation reaction. Mechanistic evidence and DFT calculations provide insights into the factors leading to high reactivity and excellent enantiocontrol in this reaction.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Organic
Linxi Yao, Alemayehu Gashaw Woldegiorgis, Xufeng Lin
Summary: Three novel axially chiral iodoarenes based on the tetramethyl-1,1'-spirobiindane skeleton were successfully synthesized, and their reactivity and selectivity were evaluated in the asymmetric oxidative formation of C-N bonds through an intramolecular desymmetrization strategy, resulting in high enantiomeric excess and yield.
TETRAHEDRON LETTERS
(2022)
Article
Chemistry, Organic
Alemayehu Gashaw Woldegiorgis, Haorui Gu, Xufeng Lin
Summary: The organocatalytic asymmetric reactions of C2-unsubstituted racemic naphthyl-indoles with orthoalkynylnaphthols were used to synthesize axially chiral styrenes connected to an axially chiral naphthyl-indole unit. By employing chiral phosphoric acid as the catalyst, these axially chiral styrenes were obtained in good yields (up to 96%) and excellent stereoselectivity (up to >99.9% ee, >20:1 dr, and >99:1 E/Z) under mild conditions. Furthermore, further synthetic transformations were achieved with high yields and excellent stereocontrol.
Article
Chemistry, Organic
Kanghua Rui, Haorui Gu, Alemayehu Gashaw Woldegiorgis, Xufeng Lin
Summary: A novel chiral phosphoric acid-catalyzed tandem regioselective 1,6-addition/double intramolecular nucleophilic addition annulation of the propargylic 3-methyleneindoles in situ generated from a-indolyl propargylic alcohols with 2-indolylmethanols has been developed, affording the new chiral trifluoromethyl pentalenobisindoles bearing an all-carbon quaternary stereogenic center in generally good yields with excellent enantioselectivities.
Article
Chemistry, Multidisciplinary
Jin Jiaping, Alemayehu Gashaw Woldegiorgis, Xufeng Lin
Summary: Here, we report an enantioselective protocol for the chiral phosphoric acid-catalyzed addition of 3-arylisoxazol-5-amines to highly reactive 3-methide-3H-pyrroles. This protocol provides a diverse range of heterotriarylmethanes bearing an amino acid moiety in good yields (up to 97%) and high enantioselectivities (up to 93% ee) under mild conditions. The utilization of a chiral spirocyclic phosphoric acid is crucial in converting the initial 1H-pyrrol-3-yl carbinols into reactive 3-methide-3H-pyrroles and achieving the desired enantioselective transformation.
Review
Chemistry, Physical
Alemayehu Gashaw Woldegiorgis, Zhao Han, Xufeng Lin
Summary: This review covers the progress achieved in chiral phosphoric acid (CPA)-catalyzed organic reactions, highlighting its versatility in various reaction types and the synthesis of enantioselective organic products of importance in biological and pharmaceutical chemistry.
JOURNAL OF MOLECULAR STRUCTURE
(2024)
Article
Chemistry, Multidisciplinary
Zhao Han, Jiaping Jin, Alemayehu Gashaw Woldegiorgis, Xufeng Lin
Summary: An efficient organocatalytic method has been developed for the synthesis of enantioenriched triflouromethylated indolin-2-ones bearing adjacent tertiary chiral centers. The use of a newly developed chiral spirobiindane-derived squaramide catalyst is essential in achieving high diastereo- and enantioselectivities.
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.
