Article
Biochemistry & Molecular Biology
Yasushi Yoshida, Hidetoshi Ida, Takashi Mino, Masami Sakamoto
Summary: 1,2,4-Triazole and 1,2,4-triazoline are important components in bioactive molecules and catalysts for organic synthesis. Efficient synthesis of these components has been extensively studied, but their structural diversity remains underexplored. In this study, we demonstrate a formal [3 + 2] cycloaddition reaction between α-imino esters and azo compounds under Bronsted base catalysis, yielding 1,2,4-triazolines in high yields. This reaction allows the general preparation of 3-aryl pentasubstituted 1,2,4-triazolines for the first time, regardless of the steric and electronic properties of the substrates and reactants. Mechanistic studies suggest that the reaction proceeds without isomerization into the aldimine form.
Article
Chemistry, Multidisciplinary
Shiqun Xiang, Weibin Fan, Wei Zhang, Yinghua Li, Shiwei Guo, Deguang Huang
Summary: A simple and green method for the synthesis of fused pyridines was developed using the [2 + 2 + 1 + 1] cycloaddition of ketones with an ammonium cation under a CO2 atmosphere. Monoethanolamine (MEA) was used as an additive to increase the solubility of CO2 in an aqueous solution. The products, exhibiting photosensitivity, show potential applications as organic optoelectronic materials, with a proposed reaction mechanism based on experimental studies.
Article
Chemistry, Applied
Xiaolan Li, Xiuqi Zhang, Fukuan Zhang, Xuzhong Luo, Haiqing Luo
Summary: In this study, a Mn(OAc)(2)-promoted formal dehydrative dehydroaromatizing [4 + 2] cycloaddition of enamides with maleimides was developed to construct pyridine rings and access diverse synthetically valuable pyrrolo [3,4-c]-pyridine derivatives. This method enables the formation of two C-C bonds for assembling pyridine derivatives from readily available enamides and inexpensive maleimides, demonstrating broad substrate scope and good functional group compatibility.
ADVANCED SYNTHESIS & CATALYSIS
(2022)
Article
Chemistry, Inorganic & Nuclear
Xusheng Guo, Chao Li, Weibo Wang, Yuanjun Hou, Baowen Zhang, Xuesong Wang, Qianxiong Zhou
Summary: The steric hindrance effect plays an important role in the activity improvement of water reduction catalysts. The replacement of a pyridine group in the TPA ligand by quinoline and isoquinoline can significantly enhance the H-2 evolution efficiency of polypyridyl Co complexes.
DALTON TRANSACTIONS
(2021)
Article
Chemistry, Multidisciplinary
Shuai Zhu, Jian-Hui Mao, Jun Kee Cheng, Shao-Hua Xiang, Bin Tan
Summary: Studies of axial chirality are an important part of modern chemistry research, and this paper describes a method for exploiting chiral molecules. Through two efficient synthetic strategies, structurally diverse analogs can be synthesized with excellent stereocontrol. These findings expand the current library of axially chiral compounds and provide new directions for exploring other axially chiral molecules with different skeletal frameworks.
Article
Chemistry, Organic
Hao-Jin Xu, Cui-Ting Li, Can-Ming Chen, Jie Chen, Xin-Qi Zhu, Bo Zhou, Long-Wu Ye
Summary: An efficient copper-catalyzed formal [4 + 1] annulation reaction of N-propargyl ynamides with diketones is described, enabling practical and atom-economic synthesis of valuable pyrrole-substituted dioxoles in generally moderate to excellent yields under mild reaction conditions. Thus, two new five-membered heterocycles can be constructed in one step through this vinyl cation chemistry.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Chun-Bao Miao, Hai-Tao Yang, Hong-Rong Guan, YiHan Tang, Kun Wang, Wen-Long Ren, Xinyu Lyu, ChangSheng Yao
Summary: A novel copper-catalyzed bisannulation reaction was developed for the concise synthesis of structurally novel dihydroindolizine-fused pyrrolidinones and their analogues, showing excellent regioselectivity and stereoselectivity. The generated products can be easily functionalized through various reactions.
Article
Chemistry, Organic
Anirban Bera, Sk Abulkalam Azad, Prasanta Patra, Nayim Sepay, Rathin Jana, Tapas Das, Amit Saha, Shubhankar Samanta
Summary: Here, a weak acid-promoted tandem aza-Michael-aldol strategy has been presented for the synthesis of diversely fused pyrrolo[1,2-a]quinoline. The protocol allows for the construction of both pyrrole and quinoline ring in one pot, forming two C-N bonds and one C-C bond under transition-metal-free conditions. A ketorolac drug analogue and a tricyclic pyrrolo[1,2-a]quinoline fluorophore were successfully synthesized, with the latter being used to detect picric acid via fluorescence quenching.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Inorganic & Nuclear
Yuji Mikata, Mizuho Uchida, Hinata Koike, Sunao Shoji, Yutaka Ohsedo, Yasushi Kawai, Takashi Matsuo
Summary: Eighteen mononuclear copper(II) complexes with oxygen-containing N4O1 pentadentate ligands were synthesized and the effects of substitution of (iso)quinoline heteroaromatics at different positions on the properties of copper(II) complexes were investigated. The results indicate that the steric hindrance caused by the peri hydrogen atom in quinoline at the Ar-3 position enhances the coordination ability of quinoline nitrogen and ether oxygen atoms to the metal center. The quinoline substitution at the Ar-3 site exhibits an opposite effect compared with those at the Ar-1 and Ar-2 sites in the absorption spectra.
DALTON TRANSACTIONS
(2023)
Article
Chemistry, Organic
Fang Hu, Yunpeng Chu, Zhengqiang Cao, Yucheng Li, Xin-Ping Hui
Summary: An efficient method utilizing the in situ generation of C-nucleophiles by an iridium catalyst in an asymmetric formal [5+1] annulation reaction has been developed for the synthesis of tetrahydropyridine derivatives. This methodology allows for the direct synthesis of a wide range of chiral tetrahydropyridine derivatives with moderate to good yields and excellent enantioselectivity.
Review
Chemistry, Multidisciplinary
Priyankar Pradhan, Ipsita Das, Saradindu Debnath, Syaleena Parveen, Tapas Das
Summary: Tropones are commercially available and valuable non-benzenoid aromatic compounds that are widely used in synthetic organic chemistry and other mechanistic studies. They exhibit versatile behavior as cycloaddition partners and are important in the synthesis of bioactive molecules. Tropones are significant scaffolds in pharmaceutical chemistry.
Review
Chemistry, Organic
Hengrui Huo, Yuefa Gong
Summary: Heterocyclic rings are fundamental building blocks in biological systems and have wide applications in synthetic chemistry and medicinal science. The development of novel synthetic methodologies for constructing heterocyclic skeletons from various starting materials has made significant progress in recent decades. Additionally, highly strained cyclopropenes as reactive reagents have attracted much attention in organic transformations.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Organic
Jian Yang, Siliang Ming, Gang Yao, Haifeng Yu, Yu Du, Jun Gong
Summary: An efficient asymmetric [4 + 2] cyclization reaction has been developed using a chiral-at-metal rhodium complex as the catalyst. Enantioenriched chroman derivatives with multiple stereocenters were obtained in high yields and good stereoselectivities. This reaction represents the first catalytic asymmetric [4 + 2] cyclization using chiral Lewis acids as catalysts and provides a useful method for constructing chiral chroman skeletons.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Editorial Material
Chemistry, Organic
Suman K. Saha, Anshul Jain, Akanksha Kumari, Tshering Sangmo Bhutia, Chanchal Agrawat, Nirmal K. Rana
Summary: A simple, mild, and metal-free cascade reaction has been developed for the construction of highly functionalized olefins. The method has a broad substrate scope and allows for substrate recycling.
Review
Chemistry, Multidisciplinary
Calum McLaughlin, Andrew D. Smith
Summary: Ammonium enolates are powerful synthetic intermediates generated catalytically using isothiourea Lewis base organocatalysts, and have been applied in selective alpha-functionalisation reactions with various precursors. Their utility in intra- and intermolecular C-C and C-X bond forming processes with electrophiles is showcased using different catalyst turnover approaches.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Review
Chemistry, Multidisciplinary
Dan He, Yawen Li, Fuwen Zhao, Yuze Lin
Summary: High trap density in organic solar cells leads to localized charge carriers and reduced carrier lifetime, limiting device efficiency. This feature article summarizes the recent advances of trap suppression by material design and device engineering.
CHEMICAL COMMUNICATIONS
(2024)
Review
Chemistry, Multidisciplinary
Olivier Monfort, Arshitha Madhusudhan, Martin Motola
Summary: This article presents the advantages of coupling photocatalysis and Fenton-based processes for environmental remediation and discusses their synergy. It critically examines the simultaneous triggering of these two processes and provides insights into research approaches. The study aims to enhance understanding of this complex process and highlight the potential integration of new catalysts in current wastewater treatment technology.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Manideepa Dhar, Chittaranjan Mishra, Avijit Das, Uttam Manna
Summary: An approach of 'polymerization of monomers in its aggregated form' has been introduced to tailor the water wettability of fibrous and porous substrates, achieving hydrophobicity to superhydrophobicity transition, as well as patterned wettability. This facile chemical method provides a durable coating with adjustable and patterned wettability for various potential applications.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Saswat Ranjan Bhoi, Chhanda Debnath, Shikha Gandhi
Summary: In this article, a novel catalytic reaction using Pd(0) and Bronsted acid is reported for the synthesis of biologically important imidazolidinone-fused N-heterocycles through redox-neutral intramolecular N-allylation of indoles and pyrroles with alkynes. This atom-economical method is applicable to a wide range of substrates and eliminates the need for leaving groups or oxidizing agents commonly used in traditional allylation reactions.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Longkun Chen, Mingshuai Zhang, Meichen Liu, Zhuoyuan Liu, Yuetong Qiu, Zhilai Zhang, Fuchao Yu, Jiuzhong Huang
Summary: In this study, an efficient Rh(III)-catalyzed selective mono- and dual-C-H bond functionalization/cyclization with iodonium ylide as the sole coupling partner was demonstrated. Fused benzodiazepine skeletons were obtained in excellent yields, providing an improved approach to dual C-H unsymmetrical functionalization.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Alice Kennett, Sven Epple, Gabriella van der Valk, Irene Georgiou, Evelyne Gout, Romain R. Vives, Angela J. Russell
Summary: This study presents the design and synthesis of sulfated disaccharide inhibitors based on IdoA(2S)-GlcNS(6S), which showed potent inhibition of Sulf-2. The results suggest that IdoA(2S)-GlcNS(6S) is the shortest fragment size required for effective inhibition of Sulfs, and a trisulfated disaccharide is identified as the minimal fragment size of heparan sulfate for effective endosulfatase inhibition.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Mauro Garbini, Andrea Brunetti, Riccardo Pedrazzani, Magda Monari, Massimo Marcaccio, Giulio Bertuzzi, Marco Bandini
Summary: The self-adaptability of galvanostatic electrolysis was found to be helpful in a multistage chemo- and diastereoselective electrochemically promoted cyclodimerization of chalcones. Through a series of reductive events, densely functionalized cyclopentanes with five contiguous stereocenters were obtained (25 examples, yields up to 95%, dr values up to >20:1). Further experimental and electrochemical investigations indicated the crucial role of dynamic kinetic resolution of the aldol intermediate in the reaction mechanism.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Dhananjay S. Nipate, Neha Meena, Prakash N. Swami, Krishnan Rangan, Anil Kumar
Summary: In this study, the synthesis of functionalized benzo[a]phenazines and indazolo[2,3-a]quinolines was achieved through Rh(III)-catalyzed oxidative annulation of 2-arylquinoxalines and 2-aryl-2H-indazoles with allyl alcohols. The method showed a wide substrate scope, excellent functional group tolerance, good to high yields of annulated products, and the capability for scaled-up synthesis. A tentative mechanism of the annulation reaction was proposed based on a preliminary mechanistic investigation.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Ruonan Zhang, Abudukadi Tudi, Xia Yang, Xuping Wang, Zhihua Yang, Shujuan Han, Shilie Pan
Summary: A new lead tellurium borate material with a unique fundamental building block [B4O10] was synthesized and found to exhibit high birefringence. The structure-property relationship was discussed using first-principles calculations.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Amresh Kumar Singh, Baishali Thakurta, Anupam Giri, Monalisa Pal
Summary: This study introduces three key concepts for the quick synthesis of large-scale high-quality 2D materials films and their utilization in device fabrication.
CHEMICAL COMMUNICATIONS
(2024)
Article
Chemistry, Multidisciplinary
Reina Hagiwara, Shun Nishimura, Kosuke Okeyoshi
Summary: A copolymer-conjugated nanocatalytic system has been developed to improve electron transfer and enhance photoinduced H2 generation.
CHEMICAL COMMUNICATIONS
(2024)