Article
Chemistry, Organic
Alla I. Vaskevych, Nataliia O. Savinchuk, Ruslan I. Vaskevych, Svitlana V. Shishkina, Mykhailo V. Vovk
Summary: 2-butenylquinazolin-4(3H)-ones can undergo intramolecular aza-Wacker cyclization to form methylene-substituted pyrrolo(pyrido)[2,1-b]quinazolinones when treated with the catalytic system Pd(OAc)(2)/PPh3/Cs2CO3/benzoquinone in dioxane or Pd(PPh3)(2)Cl-2/t-BuONa/Cs2CO3/benzoquinone in toluene. The latter catalytic system also reacts with pentenyl(hexenyl)quinazolin-4(3H)-ones, but leads to the formation of vinyl-substituted pyrrolo(pyrido)[2,1-b]quinazolinones via competition between aminopalladation of C-H multiple bonds and allylic C(sp(3))-H bond activation.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Xinchang Li, Huiru Yang, Zheyao Hu, Xin Jin, Wenyi Zhang, Xunxiang Guo
Summary: An environmentally benign protocol of visible-light-induced reaction has been developed for the effective synthesis of 4(3H)-quinazolinones from 2-benzylaminobenzamides. The reaction proceeds well under metal-free, photocatalyst-free and mediator-free conditions, providing the corresponding quinazolinones in good to high yields. Mechanism studies suggest that a radical pathway might be involved in the reaction.
CHINESE JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Marcia Perez-Fehrmann, Victor Kesternich, Arturo Puelles, Victor Quezada, Fernanda Salazar, Philippe Christen, Jonathan Castillo, Juan Guillermo Carcamo, Alejandro Castro-Alvarez, Ronald Nelson
Summary: A novel series of 6-iodo-2-methylquinazolin-4-(3H)-one derivatives were synthesized and evaluated for their cytotoxic activity. Several compounds exhibited remarkable cytotoxic activity against various cancer cell lines. Molecular docking and 3D-QSAR analysis correlated the activity with the interaction between the compounds and dihydrofolate reductase (DHFR).
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
Quentin Dherbassy, Srimanta Manna, Chunling Shi, Watcharapon Prasitwatcharakorn, Giacomo E. M. Crisenza, Gregory J. P. Perry, David J. Procter
Summary: In this study, an enantioselective copper-catalyzed borylative cyclization was reported for the assembly of privileged pyrroloquinazolinone motifs. The reaction demonstrated high enantio- and diastereocontrol, yielding products with quaternary stereocenters. The utility of the products was further demonstrated through additional manipulations.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2021)
Article
Chemistry, Organic
Zhi Jiang, Dan-Dan Zhao, Yu-Tao Hu, Yong Rao, Shi-Yao Guo, Yao-Hao Xu, Qingjiang Li, Zhi-Shu Huang
Summary: A palladium-mediated amination method was developed for the direct modification of indolyl-4(3H)-quinazolinones, allowing the synthesis of derivatives with amino groups at all positions with good functional group tolerance. The antitumor activity of these products was also evaluated.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Review
Chemistry, Medicinal
Fabiana Plescia, Benedetta Maggio, Giuseppe Daidone, Demetrio Raffa
Summary: The quinazolinone nucleus is an important scaffold for obtaining biologically active molecules. Fused heterocycles from natural or synthetic sources are associated with a wide range of biological activities. This review focuses on 4-(3H)-quinazolinones N-3 substituted with a five-membered heterocycle containing nitrogen, sulfur, and oxygen atoms in various combinations.
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY
(2021)
Article
Chemistry, Organic
Yuxin Ding, Jinqiang Kuang, Xuqiong Xiao, Lei Wang, Yongmin Ma
Summary: An efficient iron-catalyzed cross-dehydrogenative coupling [4 + 2] annulation of secondary/tertiary anilines with quinazolinones to generate quinoline-spiroquinzolinones was reported. The reaction proceeds smoothly with a relatively broad variety of functional groups, a cheap transition metal catalyst (FeCl3), and environmentally friendly oxidant (H2O2/O2) under mild reaction conditions. Additionally, N-methylanilines were creatively employed for the first time as both methyl and methylene sources attached to the N atom of tetrahydroquinolines.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Nitwaree Palavong, Piyaporn Arunkirirote, Jumreang Tummatorn, Charnsak Thongsornkleeb, Somsak Ruchirawat
Summary: This work presents a novel approach for synthesizing quinazolino[3,2-a]quinazolinone derivatives through C-H functionalization catalyzed by ligand-free copper. The reaction offers a convenient protocol that can be applied to a wide range of substrates, yielding excellent product yields. Furthermore, this method has the advantages of generating minimal waste, short reaction times, and readily available starting materials.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Li Pang, Shu-Jun Fang, Pei-Sen Zou, Wang Wang, Jun-Cheng Su, Xiao-Qing Liu, Cheng-Xue Pan, Dong-Liang Mo, Gui-Fa Su
Summary: We report a transition-metal free [4 + 4] cycloaddition reaction between 2-alkynyl quinazolines and aza-ortho-quinone methides (ao-QMs) generated from 2-(bromomethyl)anilines, leading to the synthesis of various [1,5]diazocino[2,1-b]quinazolinones in good to excellent yields under mild reaction conditions and short reaction time. Furthermore, a [1,5]diazocino[2,1-b]quinazolinone derived from estrone was easily prepared in 30% total yield over five steps, and showed significant inhibition of nitric oxide generation in LPS-stimulated RAW264.7 cells. This method offers advantages such as broad substrate scope, gram-scale preparation, and simple purification operation without flash column chromatography.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Bin Sun, Panyi Huang, Zhiyang Yan, Xiayue Shi, Xiaoli Tang, Jin Yang, Can Jin
Summary: A novel visible-light-induced radical tandem tri-fluoromethylation/cyclization reaction of unactivated alkenes with sodium perfluoroalkanesulfinates has been developed, leading to perfluoroalkyl-substituted quinazoline alkaloids. Remarkably, this transformation can be carried out without the use of any metal catalyst, strong oxidant, or external photosensitizer.
Article
Chemistry, Organic
Parveen Kumar, Vijesh Tomar, Raj Kumar Joshi, Meena Nemiwal
Summary: This study reports the synthesis of CuO nanoparticles coated with an ionic liquid as a novel nanocatalyst, and its activity in the synthesis of N-arylnucleobase and N-aryl heterocyclic derivatives through C-N cross-coupling reaction. The nanocatalyst exhibits strong catalytic activity, ease of recovery, and recyclability.
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2022)
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, Physical
Kuruva Balanna, Soumen Barik, Shilpa Barik, Sayan Shee, Niket Manoj, Rajesh G. Gonnade, Akkattu T. Biju
Summary: While the selective synthesis of biaryls with axially chiral C-C bonds is well-known, the synthesis of compounds containing axially chiral C-N bonds is less explored, and the construction of axially chiral N-N bonds has received little attention. This study demonstrates the selective amidation reaction catalyzed by N-heterocyclic carbenes (NHCs), leading to the atroposelective synthesis of N-N axially chiral 3-amino quinazolinones. The NHC-catalyzed reaction of quinazolinones with a free N-H group and α,β-unsaturated aldehydes under oxidative conditions provides the atropisomeric quinazolinone derivatives under mild conditions and with a broad scope. Preliminary studies on experimental and density functional theory-based determination of N-N rotational barrier are also presented.
Article
Chemistry, Organic
Guanyu Zhou, Zhibin Huang, Xu Xu, Zhang Fang, Pengcheng Huang, Zefeng Deng, Bao Li, Yingsheng Zhao
Summary: A practical method using rhodium as the catalyst to synthesize quinoxalinones via intra/intermolecular amination has been developed, with a wide variety of products obtained in moderate to excellent yields. Gram-scale reactions were also achieved, highlighting the synthetic importance of this new transformation.
SYNTHESIS-STUTTGART
(2022)
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
Breanna Clarke, Khashayar Ghandi
Summary: This review provides an overview of the structure and properties of ZnO nanostructures and discusses their applications in various industries. It examines previous research on ZnO nanorod growth using UV-visible spectroscopy and scanning electron microscopy, and highlights the importance of synthesis processes in determining nanostructure properties and applications. The review also unveils the mechanism of ZnO nanostructure growth and suggests future directions for research.
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, Multidisciplinary
Amirhossein Alaghmandfard, Khashayar Ghandi
Summary: This review discusses the preparation, characteristics, and applications of g-C3N4-metal oxide-based heterojunctions. The introduction of metal oxides enhances the properties of g-C3N4, improves photocatalytic efficiency and photochemical stability, and has potential applications in water splitting, organic pollutant degradation, sensors, bacterial disinfection, and supercapacitors.
