Article
Chemistry, Organic
Tong-Yang Cao, Lin Qi, Li-Jing Wang
Summary: We describe a facile switchable regioselective 7-endo or 6-exo iodocyclization of O-homoallyl benzimidates, which provides a controllable synthesis of various iodo-substituted 1,3-oxazines and tetrahydro-1,3-oxazepines. These products can undergo further substitution reactions to yield a series of functionalized heterocyclic compounds. The developed protocol offers mild conditions, simplicity in operation, and excellent compatibility with functional groups.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Applied
Tales A. C. Goulart, Ana M. S. Recchi, Davi F. Back, Gilson Zeni
Summary: The Lewis acid-promoted cyclization reaction of benzomidazole thiols with propargyl alcohols for the selective synthesis of benzoimidazolo thiazines and benzothiazolo imidazoles is described. The reaction is regioselective and controlled by the choice of solvent. The best reaction conditions were determined through systematic study, resulting in the formation of six-membered benzoimidazolo thiazines using boron trifluoride etherate and dichloromethane as the solvent, and five-membered benzothiazolo imidazoles using the same starting material and reagents with dimethylformamide as the solvent. The proposed mechanism of the cyclization reaction is based on experimental results and control experiments.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Organic
Zhenwei Lv, Yan Li, Erik V. Van der Eycken, Lingchao Cai, Liangliang Song
Summary: In this study, a metal-free cascade cyclization method was developed for the construction of structurally novel polyheterocycles. The approach involves the use of a hypervalent iodine(iii) reagent and generates diverse N-O fused spiro polyheterocycles in high yields. The synthesized compounds exhibit good antifungal activity against crop and forest pathogenic fungi, with one compound showing superior performance compared to the positive control.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Zhenwei Lv, Yan Li, Erik V. Van der Eycken, Lingchao Cai, Liangliang Song
Summary: Here, we report a metal-free cascade cyclization reaction that constructs structurally novel polyheterocycles by utilizing a hypervalent iodine(III) reagent. Under ambient conditions, alkyne-tethered N-alkoxybenzamides undergo a 6-exo-dig cyclization/dearomatization process to generate diverse N-O fused spiro polyheterocycles in good to high yields. This method features short reaction times, broad substrate scope, easy handling, and shows promising antifungal activity against crop and forest pathogenic fungi.
ORGANIC CHEMISTRY FRONTIERS
(2023)
Article
Chemistry, Organic
Behrouz Nayebzadeh, Kamran Amiri, Hormoz Khosravi, Saber Mirzaei, Frank Rominger, Dmitry Dar'in, Mikhail Krasavin, Hamid Reza Bijanzadeh, Saeed Balalaie
Summary: A transition-metal-free postmodification of the Groebke-Blackburn-Bienayme (GBB) reaction was discovered for the synthesis of Spiro [chromene-imidazo[1,2-a]pyridin]-3'-imine. This unique transformation involves activation and reaction of the imidazole carbon atom, with KOt-Bu serving as a base in the nucleophilic reaction mechanism confirmed by DFT calculations.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Hetao Xu, Mingxing Ye, Kai Yang, Qiuling Song
Summary: This study presents a transition-metal-free cross-coupling reaction of isatogens with boronic acids through a 1,4-metalate shift of a boron ate complex. The coupling reaction provides a feasible method to deliver valuable 2,2-disubstituted indolin-3-one derivatives with excellent regioselectivity, operational simplicity, good functional group tolerance, and a broad substrate scope.
Article
Chemistry, Multidisciplinary
Lihua Xie, Yi Li, Shunxi Dong, Xiaoming Feng, Xiaohua Liu
Summary: The study demonstrates that the chiral amide-guanidine-catalyzed reaction can achieve the synthesis of chiral indolin-3-one derivatives with two contiguous tetrasubstituted stereocenters, yielding moderate to good results with high diastereoselectivities and enantioselectivities. A possible working mode was proposed to explain the chiral control of the process.
CHEMICAL COMMUNICATIONS
(2021)
Article
Chemistry, Physical
Abdulkader Baroudi, Khaled Jaradat, Amir Karton
Summary: The cyclization reactions of hex-5-yn-1-yl radical systems with different linkers were investigated, and it was found that B, Si, P, S, Ge, As, and Se linkers prefer 6-endo-dig cyclization. This research provides fundamental insights into the rational synthetic design of cyclic compounds and a new tool for cyclization preference prediction.
Article
Chemistry, Multidisciplinary
Rayees Ahmad Naikoo, Rupesh Kumar, Rashmi Sharma, Dinesh Mahajan, Gaurav Bhargava
Summary: The manuscript describes a highly regioselective 6-exo-dig iodo/bromo cyclization of functionalized N-propagyl-amino-pyrimidinones under ambient conditions, resulting in the synthesis of functionalized pteridines with excellent yields. The optimized procedures are mild, operationally simple, and effective with different substrates. The synthesis of functionalized pteridines is of great significance due to their potential pharmacological profile.
Article
Chemistry, Organic
Dakoju Ravi Kishore, Gedu Satyanarayana
Summary: This study presents an efficient and straightforward strategy for the synthesis of 2,3-disubstituted benzo[b]furans. The synthetic process involves a series of reactions, including a domino intermolecular coupling and intramolecular cyclization, resulting in a wide variety of compounds with good functional group tolerance.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Organic
Huanhuan Cui, Changhao Niu, Chun Zhang
Summary: A practical method for constructing sulfenylated indole-fused isoquinolin-6(5H)-one derivatives has been developed, utilizing eco-friendly ethanol as the solvent and air as the oxidant, making it compatible with sensitive molecular frameworks. The utility of the product was illustrated through further transformations, and the reaction mechanism was investigated through control experiments.
JOURNAL OF ORGANIC CHEMISTRY
(2021)
Article
Chemistry, Organic
Amin Rezaeifard, Mohammad Bakherad, Latifeh Navidpour
Summary: A new eco-friendly one-pot synthesis of 6-iodo-4H-pyrano[2,3-d]pyrimidin-4-ones has been reported using pyrimidine-4,6-diol, aldehydes, phenylacetylene, and iodine in water at 60 degrees C. The optimized conditions resulted in high yields of 6-iodo-5,7-disubstituted-3H-pyrano[2,3-d]pyrimidin-4(5H)-one derivatives using formaldehyde and various aromatic aldehydes. This transformation involves a domino reaction of Knoevenagel condensation and iodocyclization without the need for metal or acidic/basic catalysts.
POLYCYCLIC AROMATIC COMPOUNDS
(2022)
Article
Biochemistry & Molecular Biology
Abdelkarim El Qami, Badr Jismy, Mohamed Akssira, Johan Jacquemin, Abdellatif Tikad, Mohamed Abarbri
Summary: A small library of 1H-benzo[4,5]imidazo[1,2-c][1,3]oxazin-1-one derivatives was synthesized in good to excellent yields via a Ag2CO3/TFA-catalyzed intramolecular oxacyclization of N-Boc-2-alkynylbenzimidazole substrates. The regioselectivity of this process was high, as only 6-endo-dig cyclization was observed. The silver catalyzed 6-endo-dig cyclization of N-Boc-2-alkynylbenzimidazoles as substrates showed effectiveness and compatibility, providing a practical regioselective access to diverse 1H-benzo[4,5]imidazo[1,2-c][1,3]oxazin-1-ones in good yields.
Article
Materials Science, Multidisciplinary
Enyang Liu, Pu Gong, Liyuan Wang, Xiaojian Bi, Xiaoli Yin, Sirong Yu, Bingying Wang, Xizhen Yang
Summary: One-dimensional TiO2 nanotube array (1D-TNTs) was prepared on the surface of pure titanium mesh, and 2H phase MoS2 (2H-MoS2) was deposited on the surface of 1D-TNTs. The carrier separation efficiency of the composite material was significantly increased by constructing a Z-scheme transfer mechanism of electron-hole pairs, resulting in improved degradation of rhodamine B under simulated visible light. The stability of the composite material was tested and the main active species in the catalytic process were determined to be OH and center dot O-2(-).
APPLIED PHYSICS A-MATERIALS SCIENCE & PROCESSING
(2022)
Article
Chemistry, Organic
Yucai Tang, Yiting Yang, Qian Zhou, Jinglin Duan, Biyu Yang, Changyuan Du, Yupeng He
Summary: An efficient metal- and additive-free nitro radical-triggered addition/cyclization reaction has been developed for the synthesis of nitro-substituted indolo[2,1-alpha]isoquinoline and benzimidazo[2,1-a]isoquinolin-6(5H)-one derivatives using 2-aryl-N-acryloyl indoles/2-arylbenzimidazoles. The nitro reagent, t-BuONO, which is commercially available and low-cost, was used. The reaction exhibited mild conditions and could tolerate various functional groups, resulting in moderate to good yields. Additionally, the nitro group could be easily converted into the amino group, enabling potential applications in synthetic and medicinal chemistry.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Analytical
Muhammad Zulfajri, Ganesh Kumar Dhandabani, Hui-Fen Chen, Jeh-Jeng Wang, Genin Gary Huang
Summary: The DBPhen scaffold was proposed as a colorimetric Cu2+ sensor with great sensitivity and selectivity. The addition of Cu2+ induced a color change and a new peak in the visible range. The detection limit of Cu2+ was calculated to be as low as 0.14 µM, and the color change of the DBPhen/Cu2+ complex was reversibly restored by adding CN-.
Article
Chemistry, Medicinal
C. Y. Chen, J. J. Wang, C. L. Kao, H. C. Yeh, P. L. Song, S. L. Liu, H. M. Wu, H. T. Li, W. J. Li
Summary: A new flavanone, 5-hydroxy-7,2 ',3 ',4 ',5 ',6 '-hexamethoxyflavanone (1), was isolated from the unripe fruit peels of Citrus reticulata (Rutaceae), along with two known polymethoxyflavones. The structure of compound 1 was characterized and identified by spectral analysis.
CHEMISTRY OF NATURAL COMPOUNDS
(2021)
Article
Chemistry, Organic
Vishal Suresh Kudale, Sheng Zheng, Sheng-Hua Huang, Yu-Lun Chang, Jeh-Jeng Wang
Summary: A metal-free approach for synthesizing methylene-bridged bis-1,3-dicarbonyl compounds via cross-dehydrogenative coupling of 1,3-dicarbonyl compounds with 2-methoxyethanol is reported. This methodology has also been extended to one-step synthesis of tetra-substituted pyridine derivatives using 1,3-dicarbonyl, 2-methoxyethanol, and NH4OAc. The key advantages include the wide range of compatible substrates, the use of O-2 as the only oxidant, and the ability to synthesize biologically active compounds such as 1,4-dihydropyridine and pyrazole.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Mohana Reddy Mutra, Jing Li, Yu-Ting Chen, Jeh-Jeng Wang
Summary: In this study, time-atom economic regio- and chemoselective sulfonyl radical triggered 5-exo-dig cyclization of unactivated 1,6-enynes with sulfonyl halides was developed under metal, additive-free reaction conditions to obtain highly substituted five-membered heterocyclic compounds. This transformation involves the formation of three new bonds, including C-SO2, C-C, and active C-I/Br bonds. Importantly, the one-pot protocols allow for direct synthesis of desired products from sodium sulfinates and have additional advantages such as reducing chemical waste, saving time, and simplifying practical aspects compared to existing protocols.
CHEMISTRY-A EUROPEAN JOURNAL
(2022)
Article
Biochemistry & Molecular Biology
Bo-Kai Fang, Chia-Yen Dai, Scott Severance, Chi-Ching Hwang, Chien-Hui Huang, Sin-Yu Hou, Bao-Lin Yeh, Ming-Mao Gong, Yun-Hao Chou, Jeh-Jeng Wang, Tzu-Pin Wang
Summary: This study reports the synthesis of two fluorescence chemical probes capable of quantifying PON1 lactonase activity. One of the probes showed outstanding reactivity and specificity based on reaction analysis and spectroscopic studies. The assay based on this probe was successfully used to determine PON1 activity in human sera.
Article
Multidisciplinary Sciences
Mohana Reddy Mutra, Jeh-Jeng Wang
Summary: This paper presents a method for the cleavage, migration, and functionalization of C(sp)-N bonds in ynamides under blue LED light without the use of metals or additives. This method has important implications in the synthesis of specific compounds.
NATURE COMMUNICATIONS
(2022)
Article
Chemistry, Applied
Mohana Reddy Mutra, Yu-Ting Chen, Jeh-Jeng Wang
Summary: We have developed a photoinduced sulfonyl radical-triggered cyclization of 1,6-dynes without metals, oxidants, or additives. The reaction forms three new bonds (-SO2-C, C-C, and C-I/C-Se-) under mild conditions with excellent selectivity. The conversion is economically and atomically efficient, and can be easily scaled up. Mechanistic studies reveal that the reaction proceeds through a radical pathway. Subsequent synthetic transformations of the products result in various substituted compounds. Notably, a selective C-C single bond cleavage with boronic acid insertion was observed under Suzuki reaction conditions.
ADVANCED SYNTHESIS & CATALYSIS
(2023)
Article
Chemistry, Multidisciplinary
Babasaheb Sopan Gore, Jeh-Jeng Wang
Summary: Here, we report a photoinduced energy-transfer catalysis reaction of tethered conjugated dienes, enabling the synthesis of bridged cyclopropanes. This single-step reaction efficiently generates complex tricyclic compounds with multiple stereocenters from readily accessible starting materials. The reaction demonstrates a broad substrate scope, atom-economy, excellent selectivity, and satisfactory yield, including facile scale-up synthesis and synthetic transformation. An in-depth mechanistic study reveals that the reaction proceeds via an energy-transfer pathway.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Mohana Reddy Mutra, Jing Li, Jeh-Jeng Wang
Summary: We efficiently synthesized tetrasubstituted olefins in a highly selective and stereoselective manner using sulfonyl iodides from ynamides and internal alkynes under blue LED irradiation in just a few minutes. This metal-free, user-friendly, and environmentally friendly approach showed broad applicability, as demonstrated by the successful gram-scale experiment and subsequent transformation of the sulfonyl-iodinated products into diverse compounds.
CHEMICAL COMMUNICATIONS
(2023)
Article
Chemistry, Multidisciplinary
Babasaheb Sopan Gore, Lin-Wei Pan, Jun-Hao Lin, Yi-Chi Luo, Jeh-Jeng Wang
Summary: Here, we report a visible light-promoted intramolecular radical cascade reaction for the construction of fluorenol and naphthalene-fused cyclopropyl carbaldehyde derivatives. This method offers mild reaction conditions, a broad substrate scope, excellent step efficiency, and scalability, without the need for external chemical oxidants. The novelty of this protocol was demonstrated by synthesizing chrysene analogs and performing late-stage functionalizations.
Correction
Chemistry, Multidisciplinary
Babasaheb Sopan Gore, Chiao-Ying Kuo, Jeh-Jeng Wang
CHEMICAL COMMUNICATIONS
(2022)
Article
Medical Laboratory Technology
Chien -Hui Huang, Yi-Ting Chang, Scott Severance, Jui-Ying Feng, Sin-Yu Hou, Ming-Mao Gong, Chi -Ching Hwang, Chia -Yen Dai, Jeh-Jeng Wang, Tzu-Pin Wang
Summary: This study demonstrates that serum samples stored at -80℃ can accurately determine BChE activity within 90 days, but BChE activity noticeably decreases after 90 days.
PRACTICAL LABORATORY MEDICINE
(2022)
Article
Chemistry, Multidisciplinary
Vishal Suresh Kudale, Ching-Piao Chu, Jeh-Jeng Wang
Summary: This study developed a novel method for the selective nitrosation of imidazo[1,2-a]pyridine derivatives using AgNO3 as a NO source. The protocol showed low toxicity, mild reaction conditions, and broad functional group tolerance, making it significant for synthetic transformations and gram-scale experiments.
NEW JOURNAL OF CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Babasaheb Sopan Gore, Chiao-Ying Kuo, Jeh-Jeng Wang
Summary: An atom-economic, efficient, and highly convenient method for constructing spiro[furan-3,1'-indene] skeletons from isocyanides and 1,5-enynes via synergistic nickel- and iridium-photocatalysis is reported. The spirocyclization reaction is conducted under practical and mild conditions, with excellent functional group tolerance, gram-scale synthesis and broad substrate scope for representative synthetic transformations.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Vishal Suresh Kudale, Mohana Reddy Mutra, Ching-Piao Chu, Jeh-Jeng Wang
Summary: The study outlines a process in which PEG-400 is converted into acetyl radicals through aerobic oxidative tandem conversion, followed by silver-catalyzed addition to the C-3 position of quinoxalin-2(1H)-one. This environmentally-friendly protocol utilizes PEG-400 as the acetyl source and solvent, allowing for a broad range of electron-deficient quinoxalin-2(1H)-one compounds to be coupled with in situ generated acetyl radicals in a menisci-type reaction.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Organic
Faiza Diaba, Gisela Trenchs
Summary: The first violet light-mediated synthesis of gamma- and delta-lactams from N-alkenyl trichloroacetamides is reported in this paper. The reactions are conducted in tetrahydrofuran or 2-methyltetrahydrofuran as the sole solvent without catalysts or additives, under non-anhydrous conditions in an air atmosphere where the solvent serves as the radical initiator.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Feroze Hussain, Sajjad Ahmed, Ashiq Hussain Padder, Qazi Naveed Ahmed
Summary: This study reports a novel and efficient one-pot synthesis method for mixed phosphorotrithioates, which does not require supplementary additives and shows broad applicability.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Hyunjin Oh, Ikyon Kim
Summary: A new 1,2,4-triazole-pyrrolo[1,2-a]pyrazine hybrid system, 6-acylpyrrolo[1,2-a][1,2,4]triazolo[5,1-c]pyrazine, was synthesized using a catalyst-free method. This method involved sequential exposure of pyrrole-2-carbonitrile-derived substrates to DMF-DMA and acyl hydrazide, resulting in the formation of acylated pyrazine and 1,2,4-triazole rings, enabling the installation of various substituents at specific positions on the core skeleton.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Ming Yan, Si-fan Wang, Yong-po Zhang, Jin-zhong Zhao, Zhuo Tang, Guang-xun Li
Summary: Here we developed an efficient photocatalytic approach for the convenient preparation of sulfinamides. The reaction allows for the gram-scale preparation of sulfinamides and the one-pot synthesis of various sulfonyl amides.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Farzaneh Bandehali-Naeini, Zahra Tanbakouchian, Noushin Farajinia-Lehi, Nicolas Mayer, Morteza Shiri, Martin Breugst
Summary: Two tandem catalytic systems were developed for the synthesis of novel 3,4-disubstituted maleimides using the same Ugi adducts. Different maleimide structures can be synthesized using either Pd or Cu catalysis.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Article
Chemistry, Organic
Tanya Raghava, Anjan Chattopadhyay, Subhadeep Banerjee, Nivedita Sarkar
Summary: Amine substitution of two ortho fluorine atoms of tetrafluoroterephthalonitrile through SNAr chemistry is easily achievable. But further fluorine substitution is only possible under forcing conditions, yielding valuable fluorophores for bioimaging.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
Review
Chemistry, Organic
Anju Chadha, Santosh Kumar Padhi, Selvaraj Stella, Sowmyalakshmi Venkataraman, Thangavelu Saravanan
Summary: Alcohol dehydrogenases are enzymes that use cofactors for oxidation or reduction reactions of alcohols or carbonyl compounds. They are utilized in green chemistry and have applications in the production of pharmaceuticals. Recombinant enzymes have solved the challenge of producing purified enzymes in large quantities. Engineered alcohol dehydrogenases have been used in asymmetric synthesis in industry. Various methods have been established for regenerating expensive cofactors to make the enzymatic process more efficient and economically viable.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2024)
