Article
Chemistry, Multidisciplinary
Xunming Su, Zhong-Pan Hu, Jingfeng Han, Yingxu Wei, Zhongmin Liu
Summary: In this study, ferrous gluconate is developed as an efficient metal precursor for incorporating Fe atoms into the MFI siliceous zeolite framework. The soluble and stable properties of ferrous gluconate under alkaline conditions allow it to participate in the whole crystallization process. The selectively incorporated tetrahedrally coordinated Fe atoms in the Fe-MFI zeolite demonstrate high catalytic activity, propylene selectivity, and durability in propane dehydrogenation.
CRYSTAL GROWTH & DESIGN
(2023)
Article
Chemistry, Organic
Nai-Chen Hsueh, Shin-Mei Chen, Chun-Yi Lin, Meng-Yang Chang
Summary: This paper describes a concise method for the synthesis of 1-arylisoquinolines via intermolecular cyclocondensation of oxygenated arylacetic acids with arylaldehydes in the presence of NH2OH and alcoholic solvents under mild conditions. A plausible mechanism is discussed, with only water generated as a byproduct. The protocol provides an effective ring closure through the formation of a C-C bond, two C-N bonds, and a C-O bond.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Organic
Subrata Sahoo, Shantanu Pal
Summary: A novel and efficient method for synthesizing quinazolinones via copper-catalyzed one-pot synthesis has been developed using urea, hydrazine hydrate, and atmospheric oxygen as reagents, showing good adaptability and a wide range of substrates.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Ravuri Srinath, Arindam Manna, Subhankar Shee, Vijay Babu Pathi, Saswati Ghosh, Krishnendu Khamaru, Nakul Chandra Maiti, Biswadip Banerji
Summary: A one-pot protocol for synthesizing tetracyclic triazole-piperazine-quinazolinone-fused N-heterocyclic scaffolds is reported, utilizing tandem click and cross-dehydrogentive coupling reactions with high atom economy. The method is highly functional group tolerable and has a broad substrate scope, with some derivatives showing strong white solid-state fluorescence.
Article
Chemistry, Organic
Bin Wu, Qixin Duan, Fengyuan Chen, Yingying Xu, Qi Zhang, Xiuzhi Xu, Jin Lin
Summary: An operationally simple electrochemical approach using low-cost and environmentally friendly FeCl3 as electrocatalysts has been developed for the synthesis of quinazolinones. By using readily available o-aminobenzamides and alcohols, the Fe/acid electrocatalytic system can produce quinazolinones in moderate to good yields through an indirect anodic oxidation/cyclization/dehydrogenation cascade under mild conditions. This method provides a practical and environmentally benign route for the preparation of quinazolinone derivatives.
Article
Chemistry, Organic
Amol V. Sapkal, Jaysing M. Dinore, Ajeet A. Yelwande, Manoj P. Palve, Balaji R. Madje
Summary: The N-methyl pyridinium tosylate (NMPyTs) ionic liquid serves as an efficient and recyclable catalyst for the synthesis of tetrahydropyridine derivatives through a one-pot multi-component condensation reaction. This protocol demonstrates simplicity, short reaction times, mild conditions, and high yields, with the catalyst retaining its activity for up to three recycle runs.
POLYCYCLIC AROMATIC COMPOUNDS
(2023)
Article
Chemistry, Organic
Rong Feng, Lang Huang, Da-Bin Qin, Fang Zhou, Zhi-Bing Dong
Summary: An effective method for the one-pot synthesis of N-acylated urea derivatives was explored using substituted isothiocyanatobenzenes, primary amines, and PIDA. This method offers mild reaction conditions, short reaction time, high efficiency, and readily accessible materials, making it a suitable and alternative approach for the preparation of various biologically or pharmaceutically active compounds.
TETRAHEDRON LETTERS
(2023)
Article
Chemistry, Organic
Chatrasal S. Rajput, Shweta Srivastava, Ashish Kumar, Arunendra Pathak
Summary: A new method has been developed for the preparation of dihydroquinazolin-4(1H)-ones from anthranilamide and aromatic aldehydes using the Mukaiyama reagent. The reactions proceed smoothly with high yields, low environmental impact, and high atom economy. The metal-free condition and ease of product isolation are highlighted advantages in addressing trace metal contamination in synthesized pharmaceuticals.
TETRAHEDRON LETTERS
(2021)
Article
Chemistry, Organic
Nagaraju Sakkani, Dhiraj Kumar Jha, Nouraan Sadiq, John C. -G. Zhao
Summary: A one-pot alkylation-aminoxidation reaction of styrene derivatives was achieved by in situ-generated alkyl and N-oxyl radicals. The corresponding O-alkylated hydroxylamine derivatives were obtained in moderate to good yields. The reaction involves the use of phenyliodine(iii) dicarboxylates for the generation of alkyl radicals and oxidants for N-oxyl radicals, along with the first generation of beta-enaminyl radicals through a HAT process and their use as single-electron donors.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Organic
Yi Lin, Shu-Fan He, Hui Geng, Yu-Chen Xiao, Kan-Lei Ji, Jian-Feng Zheng, Pei-Qiang Huang
Summary: A facile method for the preparation of 2,3-dialkylsubstituted quinazolinones from readily available N-arylamides and commercial isocyanates was developed, which involves the activation of the secondary amide with Tf2O/2-Br-Pyr, sequential addition of isocyanate, and cyclization. The mild reaction is general for a wide range of substrates and can be run on a gram scale.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Pushpendra Yadav, Sourabh Yadav, Annapurna Awasthi, Mandalparthi Phanindrudu, Suman Bhowmick, Dharmendra Kumar Tiwari
Summary: A new method for the synthesis of N-alkylated quinazolinones has been developed using readily available starting materials and an oxidizing agent. This efficient and metal-free approach utilizes DMSO as a solvent and a dual carbon synthon, leading to environmentally benign synthesis of medicinally prevalent compounds.
NEW JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Rajib Sarkar, Binoyargha Dam, Lenida Kyndiah, Fillip Kumar Sarkar, Sushmita Gajurel, Amarta Kumar Pal
Summary: Graphite oxide (GO) was developed from cheap and readily available graphite powder and used as a green heterogeneous carbocatalyst towards the synthesis of spirodibenzo[1,4]diazepine derivatives via a one-pot three-component strategy. The reaction conditions were mild and performed in aqueous ethanol medium, leading to diversely functionalized target products. The catalyst showed high catalytic activity and could be reused up to eight consecutive cycles without significant loss. The use of GO as a metal-free catalyst avoids metal impurities in the final products.
Article
Chemistry, Multidisciplinary
Chang Liu, Lu Ren, Wenbin Xu, Wenyu Li, Yulu Zhang, Dawei Zhang
Summary: An efficient one-pot synthesis of 1,2-disubstituted benzimidazoles via cyclocondensation using vitamin B-1 as catalyst under ultrasound-assisted reaction was developed. N-Ts-substituted 1,2-disubstituted benzimidazoles were obtained by adding p-toluenesulfonic acid. The method is environmentally friendly, requires no metal, has simple operation, wide substrate scope, high yield, and recyclable catalyst.
RESEARCH ON CHEMICAL INTERMEDIATES
(2023)
Article
Chemistry, Organic
Taiping Chen, Huan Yang, Shuangjun Li, Jiangping Xie, Lingyu Wei, Li Yang
Summary: This study reports a method for synthesizing biologically significant molecules using biocompatible catalysts in aqueous environments, which efficiently produces various quinazolinones using solar energy. The advantages of this method include low cost, low toxicity, and wide substrate scope.
TETRAHEDRON LETTERS
(2023)
Review
Chemistry, Organic
M. Mujahid Alam, Hari Babu Bollikolla, Mohammed Amanullah, Mohamed Hussein, Ravi Varala
Summary: In this mini-review, the widely utilized hypervalent iodine, phenyliodine(III) diacetate (PIDA), also known as (DAIB), is highlighted for its applications in organic synthesis involving rearrangement/migration reactions, along with interesting mechanistic aspects from the summer of 2015 to the present.
CURRENT ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Dongke Zhang, Jingran Zhang, Xiaoxian Li, Zhenyang Yu, Yadong Li, Fengxia Sun, Yunfei Du
Summary: Reactive organosulfenyl chlorides (ArSCl) or selenenyl chlorides (ArSeCl), generated in situ from the reaction of PhICl2 with diorganyl disulfides or diselenides, enable the intramolecular oxidative cyclization/chalcogenylation of beta,gamma-unsaturated oximes, leading to the formation of a series of chalcogenylated isooxazolines in good to excellent yield.
SYNTHESIS-STUTTGART
(2022)
Article
Chemistry, Organic
Beibei Zhang, Xiaoxian Li, Zhenkang Ai, Bingyue Zhao, Zhenyang Yu, Yunfei Du
Summary: A metal-free sulfenylation/spirocyclization of indolyl-ynones was achieved using organosulfenyl chloride, generated in situ from the reaction of disulfides and PhICl2. This cascade one-pot process allows for the selective synthesis of diverse sulfenylated spiroindolenines based on the substituent pattern at the two-position of indolyl-ynones.
Article
Chemistry, Organic
Xiaoxian Li, Beibei Zhang, Zhenyang Yu, Dongke Zhang, Haofeng Shi, Lingzhi Xu, Yunfei Du
Summary: The reaction of N-arylpropynamides with (dichloroiodo)benzene and diselenides/disulfides led to the synthesis of chalcogenylated quinolinones and spiro[4.5]trienes via intramolecular electrophilic cyclization and chalcogenylation. It was found that the substituent type on the aniline ring in N-arylpropynamide substrates determined the divergent cyclization pathways. Substrates with fluoro, methoxy or trifluoromethoxy groups at the para-position of the aniline underwent an alternative spiralization pathway to form 3-chalcogenylated spiro[4,5]trienones.
SYNTHESIS-STUTTGART
(2022)
Article
Multidisciplinary Sciences
Xuemin Li, Guangchen Li, Yifu Cheng, Yunfei Du
Summary: The application of in situ-generated hypervalent iodine species in organic transformations is a useful and powerful tool, allowing for the construction of a range of bond formats via oxidative coupling in a cyclic reaction process.
PHYSICAL SCIENCES REVIEWS
(2022)
Article
Chemistry, Applied
Xiaoxian Li, Beibei Zhang, Bingyue Zhao, Xiaofan Wang, Lingzhi Xu, Yunfei Du
Summary: In this study, the selective synthesis of 3-halogenated quinolin-2-ones was achieved through an umpolung process, resulting in high selectivity compared to previous electrophilic cyclization/halogenation reactions.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Haofeng Shi, Xingzong Wang, Xiaoxian Li, Beibei Zhang, Xuemin Li, Jingran Zhang, Jingyue Yang, Yunfei Du
Summary: In this study, the combined use of BnS(O)CF3/BnSe(O)CF3 with Tf2O was employed to achieve the efficient synthesis of 4-(trifluoromethylthio/ trifluoromethylseleno)isocoumarins from 2-alkynylbenzoates, which is of significance in biological research. The mechanistic pathway was proposed to involve interrupted Pummerer reactions followed by a concerted trifluoromethylthiolation/selenolation and lactonization process.
Article
Chemistry, Organic
Kommuru Goutham, Jingran Zhang, Yaxin Ouyang, Yunfei Du, Kang Zhao
Summary: A metal-free intramolecular oxychalcogenation approach has been developed for the divergent synthesis of isobenzofuran-1(3H)-one and 3,4-dihydroisochroman-1-one derivatives. The reaction of o-alkenyl benzoic acids/amides with PhICl2 and diphenyl disulfides/diselenides selectively affords the desired products based on the substitution type of the starting materials.
Article
Chemistry, Multidisciplinary
Shanqing Tao, Aiwen Huo, Yan Gao, Xiangyang Zhang, Jingyue Yang, Yunfei Du
Summary: The synthesis of biologically active isocoumarins containing S/SeCN was successfully achieved through the application of PhICl2/NH4SCN and PhICl2/KSeCN reagent systems, involving thio/selenocyanation and intramolecular lactonization reactions. The gram-scale synthesis, further derivatization to obtain C4 thio/selenocyanated Xyridin A, and the anti-tumor activities of the obtained products demonstrate the potential utility of this method.
FRONTIERS IN CHEMISTRY
(2022)
Review
Chemistry, Organic
Yifu Cheng, Guangchen Li, Luchen Jiang, Yunyi Dong, Xiangyu Zhan, Fengxia Sun, Yunfei Du
Summary: The chemistry of hypervalent iodine reagents has flourished in synthetic organic chemistry due to their mild oxidative properties, low toxicity, stability in air and moisture, and environmentally friendly features. They have been extensively used as non-metallic oxidants in oxidative coupling reactions, particularly in the construction of S-containing and Se-containing heterocycles or building blocks.
CURRENT ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Bingyue Zhao, Xiaoxian Li, Xiaofan Wang, Luchen Jiang, Zhe Li, Yunfei Du
Summary: The treatment of 2-alkenylanilines with PIDA and LiBr or KI in HFIP leads to the formation of 3-haloindoles via cascade oxidative cyclization/halogenation involving C-N/C-X (X = Br, I) bond formations. A proposed mechanism suggests the in situ formation of reactive AcO-X (X = Br, I) from the reaction of PIDA and LiBr/KI.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Xiaofan Wang, Bingyue Zhao, Lingzhi Xu, Xuemin Li, Haofeng Shi, Yunfei Du
Summary: In the presence of TBHP, the reaction of arylaldehydes and arylamines with NH4SCN results in a divergent Strecker synthesis, yielding aminonitriles and iminonitriles. The notable aspect of this modified Strecker reaction is the use of non-toxic NH4SCN as the cyanide source.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Applied
Zhifang Yang, Fengxia Sun, Jun Xu, Yadong Li, Kaiyue Yang, Yunfei Du
Summary: Treating 2-acetyl-1-chloro-1,2-dihydro-3H-1?(3)-benzo[d][1,2]iodazol-3-one 1 f with silver cyanate in dried chloroform gave hypervalent isocyanato-iodine(III) reagent 5 with high yield. When a mixture of chloroform and water was used as solvent, oxo-bridged 1,1'-oxybis(2-acetyl-1,2-dihydro-3H-1?(3)-benzo[d][1,2]iodazol-3-one) 6 was obtained. The structures of these two hypervalent iodine reagents were determined by X-ray crystallography, and their reactions with base, aniline, methanol, and cyclic ether were investigated. The structure of a previously reported 1-cyanato benziodoxole compound was revisited and revised.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Organic
Xuemin Li, Fengxia Sun, Haofeng Shi, Beibei Zhang, Jiaxin He, Jialiang Wu, Yunfei Du
Summary: The BnSRf (R-f = CF2H or CF3)/mCPBA/Tf2O system is an effective multicomponent reagent system for the one-pot synthesis of di/trifluoromethylthiolated heterocycles from alkynes. The reaction proceeds through a cascade sequence involving oxidation of BnSRf by mCPBA, activation of in situ-generated sulfoxide by Tf2O, and intramolecular cyclization/fluoromethylthiolation of the alkyne substrates enabled by the formed electrophilic sulfonium salt to give di/trifluoromethylthiolated heterocycles.
Article
Chemistry, Multidisciplinary
Jiaxin He, Feng-Huan Du, Chi Zhang, Yunfei Du
Summary: As an ambident nucleophile, controlling the reaction selectivities of nitrogen and oxygen atoms in amide moiety is a challenging issue in organic synthesis. Here, we present a chemodivergent cycloisomerization approach to construct isoquinolinone and iminoisocoumarin skeletons from o-alkenylbenzamide derivatives. The chemo-controllable strategy employed an exclusive 1,2-aryl migration/elimination cascade, enabled by different hypervalent iodine species generated in situ from the reaction of iodosobenzene (PhIO) with MeOH or 2,4,6-tris-isopropylbenzene sulfonic acid. DFT studies revealed that the nitrogen and oxygen atoms of the intermediates in the two reaction systems have different nucleophilicities and thus produce the selectivity of N or O-attack modes.
COMMUNICATIONS CHEMISTRY
(2023)
Article
Chemistry, Applied
Lingzhi Xu, Fengxia Sun, Hui Zhao, Haofeng Shi, Yihang Wu, Xiaoxian Li, Yunfei Du
Summary: In this study, a new method was developed to selectively synthesize quinolin-2-ones as the major products by reacting N-arylpropynamides with trifluoromethanesulfanamide. This alternative approach, differing from the traditional reaction route, has potential application in the field of biomedical research.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
