Article
Chemistry, Multidisciplinary
Kaier Wu, Yuye Bai, Dewei Chen, Lu Chen, Yubing Huang, Shuli Bai, Yibiao Li
Summary: Heterocyclic compounds are widely found in nature and drug molecules, with many nitrogen-containing heterocyclic compounds exhibiting unique activity. 1,4-dihydropyridines, for example, have good antitumor and antibacterial effects and can be used as calcium channel blockers in the treatment of cardiovascular diseases. This study successfully designed cobalt carbon nanotubes as a catalyst for the efficient synthesis of 1,4-dihydropyridines under mild conditions, with advantages including high yields, low catalyst loading, short reaction time, and recyclability.
ENVIRONMENTAL CHEMISTRY LETTERS
(2021)
Article
Chemistry, Physical
Mehmet Ersatir, Murat Turk, Elife Sultan Giray
Summary: A simple and eco-friendly method has been developed for synthesizing 1,4-dihydropyridine compounds in sub-critical ethanol with excellent yields, short reaction time, and easy work-up conditions.
JOURNAL OF SUPERCRITICAL FLUIDS
(2021)
Article
Chemistry, Applied
Challa Madhavi, Himavathi Ganja, Nagaraju Kerru, Suresh Maddila, Sreekantha B. Jonnalagadda
Summary: The study demonstrated the synthesis of composite materials with varying titanium dioxide loading on hydroxyapatite and characterized their structural properties and morphologies through a variety of analyses. The as-prepared composite materials showed efficient catalytic activity in synthesizing novel compounds with impressive yields at room temperature.
APPLIED ORGANOMETALLIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Cristina Blazquez-Barbadillo, Juan Francisco Gonzalez, Andrea Porcheddu, David Virieux, Jose Carlos Menendez, Evelina Colacino
Summary: This study investigated the solvent-free preparation of unsymmetrical N-aryl-5,6-unsubstituted-1,4-dihydropyridines (DHPs) using ball-milling. The results showed that the physical state of reactants and intermediates influenced the choice of catalyst and work-up method for recovering the final products.
GREEN CHEMISTRY LETTERS AND REVIEWS
(2022)
Article
Chemistry, Multidisciplinary
Dennis Rottschafer, Timo Glodde, Beate Neumann, Hans-Georg Stammler, Diego M. Andrada, Rajendra S. Ghadwal
Summary: The newly synthesized compound 5 is a red crystalline solid with an 8π electron C4As2 ring, exhibiting antiaromaticity. It can undergo oxidation reaction to form compound 6 with a 6π electron aromatic system.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Biochemistry & Molecular Biology
Rahul Yadav, Tasneem Parvin, Anoop Kumar Panday, Lokman H. Choudhury
Summary: This method involves a rapid catalyst-free three-component reaction in ethanol medium under reflux conditions to access styryl-linked dihydropyridines fused with naphthoquinone and pyrazole. It is notable for its catalyst-free conditions, short reaction time, high product yields, easy purification process, formation of three new bonds, and products with four different bioactive moieties.
MOLECULAR DIVERSITY
(2021)
Article
Chemistry, Multidisciplinary
Dennis A. Kutateladze, Eric N. Jacobsen
Summary: The cooperative asymmetric catalysis with hydrogen chloride (HCl) and chiral dual-hydrogen-bond donors (HBDs) was successfully applied to achieve highly enantioselective Prins cyclization reactions of a variety of simple alkenyl aldehydes. The designed chiral catalysts are able to withstand strongly acidic conditions and induce rate accelerations of 2 orders of magnitude compared to reactions catalyzed by HCl alone. It is proposed that the combination of strong mineral acids and chiral hydrogen-bond-donor catalysts may serve as a general strategy for inducing enantioselectivity in reactions requiring highly acidic conditions.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Biochemistry & Molecular Biology
Dilek Akbaslar, E. Sultan Giray, Oztekin Algul
Summary: In this study, lactic acid was utilized as a bio-based green catalyst and reaction medium for the first time to synthesize 1,2,3,4-tetrasubstituted pyrrole derivatives in high to excellent yields. Lactic acid demonstrated advantages such as shorter reaction time, ease of product isolation, higher yields, no by-products, no chromatographic process, and lower volatility. Additionally, the bio-based green solvent could be recycled and reused three times without loss of efficiency.
MOLECULAR DIVERSITY
(2021)
Article
Chemistry, Applied
David E. Scott, Mark D. Aloisio, Jose F. Rodriguez, Masato Morimoto, Robin J. Hamilton, Orain Brown, Rik R. Tykwinski, Jeffrey M. Stryker
Summary: This study found that catalytic iodine acts as a source of Bronsted acid in the presence of water, while generating iodonium ion and hydrogen peroxide to mediate the final oxidative aromatization step. Two independent catalytic cycles are driving the reaction, with complementary dual cycles working together to suppress side product formation and improve reaction efficiency.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Multidisciplinary
Henric Steffenfauseweh, Dennis Rottschaefer, Yury V. Vishnevskiy, Beate Neumann, Hans-Georg Stammler, Dariusz W. Szczepanik, Rajendra S. Ghadwal
Summary: A bordeaux-red solid compound based on an anionic dicarbene (ADC) with a central six-membered C4Sb2 ring is reported. The compound undergoes 2 e-oxidation to form a brick-red solid with unpaired electrons and lone pairs. The diradical character of the compound is calculated to be 36-39% according to different methods.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2023)
Article
Chemistry, Organic
Xian-Guan Liu, Ci-Shuang Dong, Fei Li, Bo Zhang
Summary: The study presents a manganese-mediated strategy for direct functionalization of Hantzsch esters with alkyl iodides, leading to the synthesis of valuable 4-alkyl-1,4-dihydropyridines. This practical reaction, operating under visible-light irradiation at room temperature, shows high functional-group compatibility and is suitable for gram-scale synthesis and late-stage functionalization.
Review
Chemistry, Organic
Pooja Yadav, A. Anagha Varma, A. J. Punnya, Purushothaman Gopinath
Summary: Multicomponent reactions (MCR's) offer synthetic chemists the opportunity to synthesize complex organic molecules in a single step, but their applications are limited by control difficulties of desired reactivity and selectivity with three or more components. Photoredox catalysis has gained attention from synthetic chemists for its simplicity and new reactivity. A review of existing reports is essential for the further design of photomediated multicomponent reactions.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Review
Chemistry, Multidisciplinary
Ritu Mathur, Khushal Singh Negi, Rahul Shrivastava, Rashmy Nair
Summary: This review article discusses the utilization of various nano-catalysts, nanoflakes, nanocomposites, and green-supported nanomaterials in the synthesis of biologically active pharmaceutical precursor 1,4-DHP and its derivatives since 2015. While tailored nanostructures have optimized the synthesis process, the development of greener practices for synthesizing 1,4-DHPs is still a long-term task to be accomplished.
Article
Chemistry, Applied
Mohamed Mokhtar, Tamer S. Saleh, Katabathini Narasimharao, Ebtesam Al-Mutairi
Summary: The present study focuses on the synthesis of novel Hantzsch 1,4-dihydropyridines containing diphenylsulfone moiety using modified heteropoly acid catalysts under ultrasound irradiation. The developed protocol provides a simple, efficient, and green approach for the synthesis of different 1,4-dihydropyridine derivatives. The characterized HPA supported iron phosphate nanotubes catalysts show enhanced catalytic performance and can be utilized multiple times without significant loss of activity.
Review
Chemistry, Physical
You-Dong Shao, Dao-Juan Cheng
Summary: Chiral phosphoric acid catalysis has witnessed significant development in the past two decades, with successful attempts in synthesizing enantioenriched axially chiral compounds through various strategies. This review highlights the advances in atropisomeric heterocycles construction enabled by chiral phosphoric acid catalysis, aiming to motivate continuous interest in atroposelective reactions.
Review
Chemistry, Organic
Xiao Yun Chen, Xiaotong Zhang, Jie-Ping Wan
Summary: Enaminones and analogous stable enamines are widely used as platform building blocks in organic synthesis for constructing heterocyclic compounds, especially N-heterocycles. Recently, synthetic protocols based on the C-N bond cleavage of enamines have achieved notable success in the development of transition metal-free heterocyclic product synthesis.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Organic
Fayun Chen, Li-Xia Quan, Anxi Zhou, Congbin Ji, Yanhong Li, Xianhong Zhu, Liu-Liang Mao, Jie-Ping Wan
Summary: An efficient and facile strategy was developed for the synthesis of 6-(sulfonylmethyl)phenanthridines and its derivatives through tandem sulfonylation cyclization of vinyl azides. The reaction utilizes accessible and cheap K2S2O5 as the sulfur dioxide source and achieves moderate to excellent yields with easy operation and gram-scale synthesis, as well as good functional-group tolerance.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Liu-Liang Mao, Li-Xia Quan, Yunyun Liu, Jie-Ping Wan
Summary: Nitrogenous heterocyclic compounds are important building blocks and intermediates in synthetic chemistry. The construction of these compounds in aqueous mediums has been a notable research topic due to its sustainability and the replacement of volatile organic solvents with water. This article highlights recent advancements in the synthesis of nitrogen heterocycles in aqueous mediums over the past two years.
CURRENT OPINION IN GREEN AND SUSTAINABLE CHEMISTRY
(2023)
Article
Chemistry, Organic
Huan Gao, Liyun Zhou, Jie-Ping Wan, Yunyun Liu
Summary: Rongalite has been used as a cheap and efficient carbonsynthonfor the synthesis of divergent N-heteroaromatics, including differentpyridines and quinolines. The selective synthesis of different productscan be achieved by employing enaminones or enaminones/anilines asreaction partners. Rongalite displays an evident advantage in providing products with considerably higher product yields under milder conditions compared with the reaction using conventional aldehyde synthons. The GC-MS analysis of the reaction process has been performed to probe the possible reaction mechanism.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Shanghui Tian, Yunyun Liu, Changfeng Wan, Jie-Ping Wan, Guifeng Hao
Summary: A simple and efficient method for synthesizing cinnolines is developed by reacting readily available enaminones and aryl diazonium tetrafluoroboronates. The reactions produce diversified cinnolines without the need for catalysts or additives by heating in dimethyl sulfoxide. Furthermore, the investigation of their anti-inflammatory activity reveals promising candidates, p-chlorobenzoyl (3f) and p-nitrobenzoyl (3j) cinnolines.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Demao Chen, Liyun Zhou, Chengping Wen, Jie-Ping Wan
Summary: By using readily available enaminones, aryl hydrazine hydrochlorides, and alkynes, a chemo-selective three-component synthesis of atropisomeric N-(o-alkenylaryl)pyrazoles was efficiently achieved with rhodium catalysis. Unlike the Satoh-Miura reaction, which uses pre-prepared N-phenyl pyrazoles and alkynes as substrates for alkyne-based C-H benzannulation, this three-component protocol demonstrates unprecedented selectivity of C-H alkenylation by blocking the second round metal alkenylation with the key protonation step in the presence of acids.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Yan Lin, Jie-Ping Wan, Yunyun Liu
Summary: This article describes a facile cascade reaction for the site-selective synthesis of 2-cyanochromones. By using simple o-hydroxyphenyl enaminones and potassium ferrocyanide trihydrate (K4[Fe(CN)6]3·3H2O) as starting materials, and I2/AlCl3 as promoters, the products are obtained through tandem chromone ring formation and C-H cyanation. The unconventional site selectivity is attributed to the in situ formation of 3-iodochromone and a formal 1,2-hydrogen atom transfer (HAT) process. Additionally, the synthesis of 2-cyanoquinolin-4-one has been achieved by employing the corresponding 2-aminophenyl enaminone as the substrate.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Demao Chen, Changfeng Wan, Yunyun Liu, Jie-Ping Wan
Summary: A facile and practical method for the synthesis of fused tricyclic pyrazolo[5,1-a]isoquinolines has been developed via the reactions of enaminones, hydrazine hydrochloride, and internal alkynes using Rh catalysis. The cascade reactions demonstrate the remarkable high-order bond functionalization, involving the transformation of aryl C-H, ketone C=O, and alkenyl C-N bonds in the enaminones. This study highlights the individual advantage of enaminones in the design of novel and efficient synthetic methods.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Xiao Xiao, Puren Han, Jie-Ping Wan, Jianchao Liu
Summary: An efficient and general method for the synthesis of indolyl-C-glycosides has been developed. The method exhibits excellent stereoselectivity, a wide range of substrate applicability, and mild reaction conditions. It has also been successfully applied to large-scale reactions and diversified synthetic transformations.
Article
Chemistry, Multidisciplinary
Zukang Zhong, Lihua Liao, Yunyun Liu, Ming Zhang, Jie-Ping Wan
Summary: The annulation reactions of enaminones with quinonediimides/quinoneimides for selective synthesis of indoles and 2-aminobenzofurans have been realized. Indoles were obtained via HNMe2-elimination-based aromatization with Zn(ii) catalysis, while 2-aminobenzofurans were produced via dehydrogenative aromatization with Fe(iii) catalysis.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Dingsheng Cao, Chaoli Wang, Jie-Ping Wan, Chengping Wen, Yunyun Liu
Summary: This paper describes the trifunctionalization of tertiary enaminones, specifically the selective gem- and vicinal diphosphorylation, enabling the synthesis of tunable alpha,alpha- and alpha,beta-diphosphoryl ketones. Additionally, the phosphorylation of the C-N bond with improved substrate tolerance has been achieved.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Demao Chen, Liyun Zhou, Yunyun Liu, Jie-Ping Wan
Summary: The direct three-component reactions of enaminones, aryl hydrazine hydrochlorides, and internal alkynes via Rh(iii) catalysis have enabled the synthesis of N-naphthyl pyrazoles. The use of simple substrates in these synthetic reactions results in the simultaneous construction of dual cyclic moieties, including a pyrazole ring and a phenyl ring, through the sequential formation of two C-N and three C-C bonds.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Organic
Baoli Zhao, Xiaoting Yin, Haifeng Li, Kai Cheng, Jie-Ping Wan
Summary: A metal-free dioxygenative reaction of aryl diazonium salts with aryl alkynes for vicinal diketone synthesis has been developed. The major advantages of this synthetic method are aerobic oxygenation and organic dye-based photocatalysis. A photoredox mechanism involving free radical dioxygenation is proposed based on rational control experiments.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Review
Chemistry, Organic
Jianchao Liu, Jie-Ping Wan, Yunyun Liu
Summary: This review highlights the recent progress in the development of electrochemical difunctionalization of alkenes and alkynes for the synthesis of organochalcogens. It covers various reactions such as oxychalcogenation, carbochalcogenation, aminochalcogenation, halochalcogenation, and dichalcogenation. These studies are of great significance in the field of organic synthesis chemistry.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Jingfeng Ye, Yunyun Liu, Jin Luo, Jie-Ping Wan
Summary: The synthesis of polyfunctionalized alkenes has been achieved through the transformation of enaminones, disulfides, and alcohols without the use of transition metals. Furthermore, the application of the alkene products in the synthesis of various sulfenyl heteroaryls has been demonstrated.