Article
Chemistry, Organic
Jiexiong Mai, Ziwei Huang, Shaohuan Lv, Quan Chen, Rongrong Chen, Feng Xie, Jun Wang, Bin Li
Summary: An efficient and visible light-promoted cascade N-alkylation/amidation reaction between quinazolin-4(3H)-ones and benzyl halides/allyl halides has been reported for the first time, providing a convenient approach for synthesizing quinazoline-2,4(1H, 3H)-diones. This cascade reaction shows good functional group tolerance and can also be applied to N-heterocycles such as benzo[d]thiazoles, benzo[d]imidazoles, and quinazolines. Control experiments reveal the crucial role of K2CO3 in this transformation.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Review
Chemistry, Medicinal
Hussein I. El-Subbagh, Mohamed A. Sabry
Summary: Antifolates are a class of drugs used for antibacterial, antiparasitic, and anticancer purposes. 2-substituted-mercapto-quinazolin-4(3H)-one analogues have been studied as DHFR inhibitors, with the development of compounds with significant biological activity based on a structural model. The compounds 18, 20, and 21, formulated using this model, have shown 4-8 times greater activity than the reference drug methotrexate (MTX, 1).
MINI-REVIEWS IN MEDICINAL CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Wuji Sun, Xue Ma, Yuqi Pang, Lifeng Zhao, Qidi Zhong, Chunyan Liu, Qiangwen Fan
Summary: A green, simple and efficient method for the synthesis of quinazolin-4(3H)-ones has been developed via visible light-induced condensation cyclization. The method utilizes fluorescein as a photocatalyst and TBHP as a reaction promoter without the need for a metal catalyst. The reaction demonstrates high substrate tolerance and yields a variety of desired products in good to excellent yields. This method provides a straightforward strategy for the synthesis of quinazolin-4(3H)-ones.
Article
Chemistry, Organic
Vishnuvardhan Nomula, Sadu Nageswara Rao
Summary: The KOBu-Bu-t-BF3.OEt2 mediated synthesis of quinazolin-4(3H)-ones from 2-substituted amides with nitriles and aldehydes involves the cleavage of C-X and C-N bonds and the formation of double C-N bonds, resulting in good to moderate yields of the products with the presence of potassium tert-butoxide.
SYNTHETIC COMMUNICATIONS
(2021)
Article
Biochemistry & Molecular Biology
Janez Mravljak, Lara Slavec, Martina Hrast, Matej Sova
Summary: Quinazolinones display diverse biological activities in medicinal chemistry. The study synthesized two series of 2-substituted quinazolin-4(3H)-ones and evaluated their antioxidant properties using three methods. The presence of hydroxyl groups or an ethylene linker enhanced antioxidant activity and led to metal-chelating properties in some derivatives.
Article
Chemistry, Organic
Yayue Dai, Jianhao Di, Zeyang Hao, Xiangtai Meng, Lei Zhang
Summary: A Cs2CO3-promoted domino reaction between thioaurones and sulfur ylides was developed, leading to the formation of a series of spiro[benzo[b]thiophene-2(3H),1'-cyclopropan]-3-ones in good-to-high yields. The reaction tolerated both electron-withdrawing and electron-donating groups on both thioaurones and sulfur ylides, and the mechanism and diastereoselectivity were investigated.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Biochemistry & Molecular Biology
Maria Karelou, Dionysis Kampasis, Amalia D. Kalampaliki, Leentje Persoons, Andreas Kraemer, Dominique Schols, Stefan Knapp, Steven De Jonghe, Ioannis K. Kostakis, Sotiris S. Nikolaropoulos
Summary: Sixteen new 2-substituted quinazolines were synthesized and evaluated for their anti-proliferative activity against multiple cancer cell lines. Compound 17 showed remarkable activity against the majority of tested cell lines.
Article
Chemistry, Organic
Mei Sun, Yan-Ling Yu, Long Zhao, Ming-Wu Ding
Summary: A new one-pot method for the preparation of polysubstituted quinazolin-4(3H)-ones has been developed using a sequential oxidative Ugi/Staudinger/aza-Wittig reaction. The oxidative Ugi reactions of tertiary amines, 2-azidobenzoic acids, and isocyanides produced azide intermediates, which were then treated with triphenylphosphine to yield polysubstituted quinazolin-4(3H)-ones in moderate to good yields.
Article
Chemistry, Organic
Ekaterina Levashova, Maria Adamchik, Grigory Kantin, Dmitry Dar'in
Summary: Here, a chemo- and diastereoselective formal C-C insertion reaction was described, which introduced 1,2-disubstituted 4-diazo-3(2H)-isoquinolones and 4-diazoisochroman-3-one into the C-CHO bonds of aldehydes, resulting in all-carbon α-quaternary aldehydes bearing medicinally important 1,4-dihydro-3(2H)-isoquinolone scaffold. The protocol exhibited preferential 1,2-carbon migration over the common 1,2-H shift, and the reaction tolerated various functionalities in both aldehyde and diazo components, providing the target homologated aldehydes in generally high yields. The synthetic utility of this method was further demonstrated by transformations of the formyl moiety.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Ali Akbari, Mahboobeh Zahedifar
Summary: The present study developed a new multi-component reaction for the synthesis of 2-aryl/alkyl-quinazolin-4(3H)-ones with good to excellent yields (86- 97%). The method utilized inexpensive and readily available starting materials and involved simple procedures and easy workup. Ammonium hexafluorophosphate (NH4PF6) was employed as an efficient reagent and catalyst. The synthesized compounds were characterized using 1H NMR and C-13 NMR techniques.
JOURNAL OF SAUDI CHEMICAL SOCIETY
(2023)
Article
Spectroscopy
Tatyana N. Moshkina, Emiliya Nosova, Galina N. Lipunova, Marina S. Valova, Elizaveta F. Petrusevich, Robert Zalesny, Borys Osmialowski, Valery N. Charushin
Summary: 2-(2-Hydroxyphenyl)-3H-quinazolin-4-ones with diverse substituents on the phenol ring and their six-membered difluoroboron complexes were synthesized through a few-stage approach. The photophysical properties of these compounds were studied in two solvents and in the solid state, revealing the impact of substituents and substitution points on the photophysical properties of the dyes. In a THF/water mixture, all ligands showed enhanced emission with increasing water fraction due to aggregation-induced emission.
SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY
(2021)
Article
Chemistry, Organic
Jianying Li, Zebiao Zhou, Gang Xie, Mingzhong Cai
Summary: An efficient heterogeneous palladium-catalyzed carbonylative annulation has been developed for constructing a wide variety of compounds from commercially easily available starting materials. The heterogenized palladium catalyst used in this study can be easily recovered and reused multiple times with consistent catalytic efficiency.
SYNTHESIS-STUTTGART
(2022)
Article
Chemistry, Multidisciplinary
Apurba Dutta, Diganta Sarma
Summary: A metal, solvent and oxidant free method has been developed for the synthesis of quinazolin-4(3H)-ones under microwave irradiation. Using the same catalyst, 2,3-dihydroquinazolin-4(1H)-ones were also synthesized in water as a green and sustainable solvent. These protocols offer a simplistic and rapid approach for assembling diverse structural quinazolinones.
SUSTAINABLE CHEMISTRY AND PHARMACY
(2021)
Article
Chemistry, Applied
Le-Cheng Wang, Yu Zhang, Zhengkai Chen, Xiao-Feng Wu
Summary: A procedure for the palladium-catalyzed carbonylative reaction has been developed for the synthesis of pharmaceutically valuable 2-(trifluoromethyl)quinazolin-4(3H)-ones. The transformation uses Mo(CO)(6) as both a convenient CO source and a reducing reagent. This newly developed protocol is compatible with various nitro compounds and can be readily scaled up to a 1 mmol scale.
ADVANCED SYNTHESIS & CATALYSIS
(2021)
Article
Chemistry, Multidisciplinary
Yibo Dong, Jinli Zhang, Jinchen Yang, Congcong Yan, Yangjie Wu
Summary: An efficient approach to quinazolin-4(3H)-ones was developed through a one-pot intermolecular annulation reaction, providing good functional group tolerance and high yields up to 98%. The control experiment showed that the thiol substrate can promote the dehydroaromatization step.
NEW JOURNAL OF CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Wenting Zheng, Xianlie Chen, Feng Chen, Ze He, Qingle Zeng
Summary: Sulfoximines are versatile compounds that are widely used in various fields, and can be synthesized and transformed in different ways, showing great potential for a wide range of applications.
Review
Chemistry, Organic
Qiaoling Zhang, Jufang Xi, He Ze, Zeng Qingle
Summary: Sulfinamides, especially enantiopure sulfinamides, are widely used in organic and medicinal synthesis and exhibit interesting and valuable reactivity. The latest review summarizes the development in the synthesis and transformation of sulfinamides, providing guidance for future research.
SYNTHESIS-STUTTGART
(2021)
Article
Engineering, Environmental
Wenting Zheng, Ratnakar Reddy Kuchukulla, Xiangning Xu, Dandan Zhang, Lihong Zhou, Qingle Zeng
Summary: The article introduces a novel adsorbing material CC-GP-D with comb-shaped structure, prepared with chitosan as the main chain, which shows higher adsorption efficiency and cost-effectiveness in removing heavy metal ions from sewage.
JOURNAL OF POLYMERS AND THE ENVIRONMENT
(2022)
Review
Chemistry, Multidisciplinary
Lu Yang, Bingren Wang, Xianjie Yin, Qingle Zen
Summary: Sulfenate anions as key intermediates in enantioselective synthesis have attracted attention in recent years. Developing new synthetic methods to generate sulfenate anions allows for the preparation of various enantiopure sulfoxides, which are widely used as auxiliaries, ligands, organocatalysts, and biologically active compounds. This review covers the in situ preparation methods and recent applications of sulfenate anions in catalytic asymmetric synthesis of chiral sulfoxides.
Article
Chemistry, Organic
Yiding Wang, Lei Shen, Helin Wang, Yixin Luo, Qingle Zeng
Summary: The ring-opening addition reaction of activated vinyl cyclopropanes with N-tosylhydrazones in the presence of palladium(0) and triphenylphosphine yields N-tosylhydrazone butenylmalonate compounds. Aromatic aldehyde-derived N-tosylhydrazones produce both terminal and internal N-allylated products, with the terminal products being the major ones. On the other hand, ketone-derived tosylhydrazones only yield terminal addition products. The transformation relationship between the terminal and internal N-allylated products is also observed. A reasonable mechanism based on preliminary experimental results is proposed.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Xiaokang Kang, Helin Wang, Qingle Zeng
Summary: A new method for N-sulfenylation of sulfoximines using thiosulfonates under mild conditions is disclosed in this study. A series of aliphatic and aromatic N-sulfenyl sulfoximines were synthesized with good to excellent yields without the use of transition metals. The applicability of this method was demonstrated through gram-scale experiments.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
Review
Biochemistry & Molecular Biology
Bingren Wang, Xiayu Liang, Qingle Zeng
Summary: Sulfoximines, a widely distributed structural motif in bioactive molecules and functional materials, have attracted significant attention from organic chemistry, pharmaceutical industries, and materials science. They have proven to be an effective directing group for C-H functionalization, particularly in the synthesis of cyclic sulfoximines. This review focuses on recent advances in the synthesis of cyclic sulfoximines via C-H activation strategy, categorized according to substrate types.
Article
Chemistry, Organic
Xianlie Chen, Ping Zhao, Qingle Zeng
Summary: A white light/NIS-promoted three component reaction was developed for the synthesis of organylselenylethyl sulfonylhydrazones using alkenes, N-sulfonylhydrazones, and diorganyl diselenides. The reaction was carried out under mild conditions and showed good tolerance towards common functional groups. Heteroaryl and aliphatic diselenides were also suitable substrates, and the reaction could be performed on a gram scale. The reaction exhibited a wide substrate scope, providing moderate to high yields and excellent regioselectivities. UV-visible absorption spectra confirmed the formation of photoactive intermediates, which matched the wavelength of the applied white LED. A plausible mechanism was proposed based on UV-visible light experiments and control experiments.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Qingle Zeng, Xianjie Yin, Yiding Wang
Summary: Allylic compounds are widely used in various industries, and vinylcyclopropanes have rapidly developed in organic synthesis. Activated vinylcyclopropanes are important raw materials for the synthesis of functionalized heterocyclic compounds or allyl derivatives. Transition metal-catalyzed allylation of vinyl cyclopropanes can form new bonds with nucleophiles containing different centers. This article reviews the progress on this reaction.
TETRAHEDRON LETTERS
(2023)
Article
Chemistry, Applied
Xianjie Yin, Helin Wang, Lei Shen, Qingle Zeng
Summary: A copper chloride-catalyzed three-component reaction of olefins, indoles, and diaryl diselenides under irradiation of blue LED light is presented. Various diaryl diselenides, including diheteroaryl diselenides, are suitable for this bifunctionalization of olefins. The reaction provides 26 examples of β-(hetero)arylselenyl indoles in 60%-87% yields, and the proposed mechanism involves the activation of diaryl diselenides, electrophilic addition of arylselenium cations to styrenes, and Friedel-Crafts-type alkylation at the 3-position of NH-indoles.
APPLIED ORGANOMETALLIC CHEMISTRY
(2023)
Review
Chemistry, Multidisciplinary
Lu Yang, Xiayu Liang, Yuyang Ding, Xinran Li, Xuefeng Li, Qingle Zeng
Summary: This review presents recent transition metal catalyzed transformations for the synthesis of chiral five- and six-membered benzo oxygen heterocycles and discusses in detail the reaction mechanisms and processes for chirality transfer or control.
Review
Chemistry, Multidisciplinary
Ping Zhao, Qingle Zeng
Summary: In recent years, there has been a significant increase in the prominence of enantioenriched sulfur(VI) compounds in the chemical science, particularly in the realm of bioactive molecules. However, the synthesis of these compounds has presented significant challenges, leading to the exploration of diverse synthetic methods. Therefore, this review provides an in-depth analysis of the latest advancements in the synthesis of sulfoximines, sulfonimidate esters, sulfonimidamides, and sulfonimidoyl halides since 1971.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Biochemical Research Methods
Qinqin Tang, Ping Zhao, Qingle Zeng
Summary: This paper describes the enantioseparation of 12 chiral sulfoximines on polysaccharide-based chiral stationary phases (CSPs). The investigation of chiral column, high-performance liquid chromatography parameters, such as mobile phase composition and column temperature, reveals that Chiralcel OJ-H column can resolve all of the 12 compounds, while Chiralpak AD-H column and Chiralpak AS-H column can separate eight and nine molecules, respectively. The sulfoximines are effectively resolved with Chiralcel OJ-H column using a mixture of n-hexane/2-propanol (80:20) as the mobile phase.
JOURNAL OF CHROMATOGRAPHIC SCIENCE
(2023)
Article
Chemistry, Organic
Ping Zhao, Qingle Zeng
Summary: We have developed a method for the synthesis of diverse 1-sulfonylquinazoline-2,4(1H,3H)-diones and 2-sulfonamidobenzonitriles. The method utilizes substrate control and chemoselectivity through condensation reactions. The reactions are carried out at room temperature within half an hour using easily accessible starting materials and yield moderate to excellent product yields.
JOURNAL OF HETEROCYCLIC CHEMISTRY
(2023)
Review
Chemistry, Multidisciplinary
Helin Wang, Alex Adonis Nkingwa, Fawad Islam, Chao Xu, Qingle Zeng
Summary: Organochalcogen molecules have extensive applications in various fields. The difunctionalization of olefins is a successful technique for introducing two functional moieties in a single-step reaction. The combination of olefins with diorganyl dichalcogenides effectively increases molecular complexity.
CHEMISTRY-AN ASIAN JOURNAL
(2023)
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)
