Article
Chemistry, Organic
Kailas V. Preeti, Kailas V. Kallurkar, Prathama S. Mainkar, Raju Adepu, Srivari Chandrasekhar
Summary: A concise route for the synthesis of dihydrobenzo-[j]-phenanthridinones has been developed using an aryne annulation strategy under metal-free reaction conditions. The reaction involves multiple C-C and C-N bond cleavages/formations through Diels-Alder reaction, aromatization-driven C-N bond cleavage, and amide formation.
Article
Chemistry, Organic
Kentaro Okuma, Shiho Inomata, Yuxuan Qu, Noriyoshi Nagahora
Summary: Reaction between quinoline and benzyne from benzenediazonium-2-carboxylate and chloroform yields 1-phenyl-2-trichloromethyl-1,2-dihydroquinoline in 79% yield. Basic hydrolysis of dihydroquinoline by KOH leads to the formation of 2-quinolinone in 85% yield.
Article
Integrative & Complementary Medicine
Liu Yu, You Yun-Xia, Rao Li, He Qian, Su Yu, Fan Yue, Li Yi-Zhou, Xu You-Kai, Zhang Chuan-Rui
Summary: Fourteen new geranyl phenyl ethers and three known compounds were isolated from Illicium micranthum, with some of them showing anti-HBV activity.
CHINESE JOURNAL OF NATURAL MEDICINES
(2022)
Article
Chemistry, Organic
Jonali Das, Sajal Kumar Das
Summary: This study reports that trifluoroethanol-mediated ring-opening cyclization can efficiently generate pyrano[2,3-e]indol-3-ols with high yields. The regioselective cyclization at the indole C-5 position is influenced by the presence of a pi-activating aryl substituent on the reacting epoxide carbon atom.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2021)
Article
Chemistry, Multidisciplinary
Tamiris R. C. Silva, Vinicius V. Souza, Cristiano Raminelli
Summary: In this study, we investigated the reaction of several substituted oxazoles with o-(trimethylsilyl)aryl triflates promoted by potassium fluoride and 18-crown-6-ether. We obtained functionalized isoquinoline compounds in moderate to good yields at room temperature through a [4+2] cycloaddition-ring-opening reaction pathway, followed by acidic workup. Alternatively, bicyclic ethers were produced in reasonable yields at 60 degrees C through a sequence of [4+2] cycloaddition, retro-Diels-Alder, and [4+2] cycloaddition reactions.
Article
Chemistry, Physical
Jieran Yi, Zilong Wang, Zhi Li
Summary: Enantioconvergent conversions of rac-styrene oxides to (R)-mandelic acids were achieved using an enzymatic cascade, resulting in high yields. The concept was proven using a mixture of enzymes or coupled E. coli strains.
Article
Chemistry, Organic
Xin Geng, Andrey Shatskiy, Gregory R. Alvey, Jian-Quan Liu, Markus D. Karkas, Xiang-Shan Wang
Summary: This study presents a protocol for a tandem Pd/Cu-catalyzed intermolecular cross-coupling cascade, providing a conceptually novel and controlled approach to synthesize N-fused (benzo)imidazophenanthridine scaffolds with high efficiency, broad substrate scope, and excellent functional group compatibility.
Article
Chemistry, Organic
Renate Schwiedernoch, Xiaofeng Niu, Haosheng Shu, Stephan N. N. Steinmann, Mengjia Wu, Negar Naghavi
Summary: This paper describes the development of a one-step, room temperature electrocatalytic method for the formation of stable β-lactone from CO2 and dienes, based on the in situ electrochemical formation of metal-based nanoclusters. By regulating the applied potential and current density, this one-step electrosynthesis method results in the formation of a new class of β-lactone with high selectivity (up to 100%) and activity (up to 80% yields with respect to the reacted diene). This work paves the way for more sustainable and environmentally friendly reaction pathways based on the in situ formation of nanoclusters as organic electrosynthesis catalysts.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Jixiang Ni, Matteo Lanzi, Arjan W. Kleij
Summary: An unanticipated exo-cyclic nucleophilic attack of thiol reagents on vinyl cyclic carbonates is described, leading to the synthesis of allylic thioethers. This reaction pathway adds to the reactivity modes available for these heterocycles, complementing the previously reported endo-cyclic nucleophilic attack.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Zhen Zhang, Xiangshan Fang, Ayimnisa Aili, Shilong Wang, Junhong Tang, Wanjun Lin, Lei Xie, Jinchun Chen, Kai Sun
Summary: A novel radical cascade trifluoromethylthiolation/cyclization method was developed, allowing simple and efficient synthesis of medium-sized rings (7/8/9-membered heterocycles) containing SCF3 groups through the reaction of AgSCF3 with N-alkyl-2-(1-phenylvinyl)aniline derivatives. Preliminary mechanistic studies suggest that the reaction proceeds through a silver-assisted radical cascade cyclization process. The large-scale experiment and product modification demonstrate the promising utility of this protocol.
Article
Chemistry, Organic
Shahnawaz Khan, Monish Arbaz Ansari, Maya Shankar Singh
Summary: This study presents a chemo- and regioselective cascade annulation between fi-ketothioamides and diazo-substituted hypervalent iodine reagents under transition-metal-free and base-free conditions at room temperature. A divergent construction of fused-heterocyclic scaffold thiazolothiadiazoles has been achieved with the advantages of operational simplicity, scalability, broad substrate compatibility, and mild reaction conditions. This one-pot strategy not only avoids potential toxicity but also broadens the arsenal of synthetic methods to obtain fused N,S-heterocyclic frameworks.
Article
Chemistry, Multidisciplinary
Kevin Dollberg, Selina Schneider, Roman-Malte Richter, Tobias Dunaj, Carsten von Haenisch
Summary: This article presents a synthesis route for alkali metal antimonides and investigates their stability. It demonstrates that the use of appropriate crown-ethers allows for the isolation and characterization of these compounds at room temperature. Additionally, the synthesis of the first primary silylstibane and its characterization are discussed, as well as the formation and crystal structure of (Dipp(2)NacNac)GaH(SbHSi(SiMe3)(3)).
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Physics, Multidisciplinary
Wenbin Zhao, Weiyao Ke, Wei Chen, Tan Luo, Xin-Nian Wang
Summary: The study demonstrates that the long-standing puzzle of hadron suppression factor R-AA and v(2) in high-energy heavy-ion collisions can be solved by including quark coalescence and final state hadron cascade in a coupled linear Boltzmann transport-hydro model. This approach also leads to a splitting of v(2) for pions, kaons, and protons in the intermediate p(T) region. The experimental data on R-AA, v(2), and their hadron flavor dependence can be understood within this coupled framework for low to intermediate and high pT in high-energy heavy-ion collisions.
PHYSICAL REVIEW LETTERS
(2022)
Article
Chemistry, Multidisciplinary
Kai-Qiang Tian, Tongbo Zhang, Shi-Jiao Zhang, Jun Zhao, Leilei Mao, Guiyun Duan, Hong-Shuang Li
Summary: This study developed a method for the synthesis of pyrido[1,4]oxazocines from 4-Cl- and 2-Cl-substituted 3-(oxiran-2-yl)pyridines and ethanolamines under additive-free conditions. The method exhibits regioselectivity and efficiency.
NEW JOURNAL OF CHEMISTRY
(2023)
Article
Chemistry, Organic
Thikhamporn Uppalabat, Nattawoot Hassa, Natthapat Sawektreeratana, Pawaret Leowanawat, Pattarapapa Janthakit, Phattananawee Nalaoh, Vinich Promarak, Darunee Soorukram, Vichai Reutrakul, Chutima Kuhakarn
Summary: This study investigates the persulfate-promoted radical cascade trifluoromethylthiolation and cyclization of 3-alkyl-1-(2-(alkynyl)phenyl)indoles with AgSCF3. The protocol offers a new route to CF3S-substituted indolo[1,2-a]quinoline-7-carbaldehydes and CF3S-substituted indolo[1,2-a]quinoline-7-methanone derivatives through the formation of C-SCF3 and C-C bonds, as well as benzylic carbon oxidation in a single step. The reaction is compatible with a wide range of functional groups. The chemical structure of the product is confirmed by single-crystal X-ray diffraction data.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Kentaro Okuma, Yukiko Tanabe, Noriyoshi Nagahora, Kosei Shioji
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN
(2015)
Article
Chemistry, Multidisciplinary
Noriyoshi Nagahora, Tamaki Ogawa, Maki Honda, Motomi Fujii, Hiroshi Tokumaru, Takahiro Sasamori, Kosei Shioji, Kentaro Okuma
Article
Chemistry, Organic
Kentaro Okuma, Kenta Horigami, Noriyoshi Nagahora, Kosei Shioji
SYNTHESIS-STUTTGART
(2015)
Article
Chemistry, Organic
Kentaro Okuma, Hiroaki Kinoshita, Noriyoshi Nagahora, Kosei Shioji
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2016)
Article
Chemistry, Organic
Noriyoshi Nagahora, Ikue Takemoto, Motomi Fujii, Kosei Shioji, Kentaro Okuma
Article
Chemistry, Organic
Noriyoshi Nagahora, Shuhei Yahata, Shoko Goto, Kosei Shioji, Kentaro Okuma
JOURNAL OF ORGANIC CHEMISTRY
(2018)
Article
Chemistry, Organic
Noriyoshi Nagahora, Shoko Goto, Takahiro Inatomi, Hiroshi Tokumaru, Kouki Matsubara, Kosei Shioji, Kentaro Okuma
JOURNAL OF ORGANIC CHEMISTRY
(2018)
Article
Chemistry, Organic
Noriyoshi Nagahora, Hiroshi Tokumaru, Shinpei Ikaga, Takuya Hanada, Kosei Shioji, Kentaro Okuma
Article
Chemistry, Organic
Kentaro Okuma, Kazunori Munakata, Hiroyuki Matsui, Noriyoshi Nagahora, Kosei Shioji
Article
Chemistry, Inorganic & Nuclear
Noriyoshi Nagahora, Tomoko Kushida, Kosei Shioji, Kentaro Okuma
Article
Chemistry, Organic
Noriyoshi Nagahora, Kana Kitahara, Yoshiyuki Mizuhata, Norihiro Tokitoh, Kosei Shioji, Kentaro Okuma
JOURNAL OF ORGANIC CHEMISTRY
(2020)
Article
Chemistry, Organic
Noriyoshi Nagahora, Rina Tanaka, Tomoyo Tada, Akira Yasuda, Yuji Yamada, Kosei Shioji, Kentaro Okuma
Article
Chemistry, Physical
Yuji Yamada, Kohei Nishizono, Mai Kano, Satomi Koreki, Noriyoshi Nagahora, Yoshinori Nibu
Summary: In this study, conformer-selected electronic and vibrational spectra of benzylmethyl ether and its terminal methyl group-substituted derivative were measured using UV-UV hole burning and fluorescence-detected infrared spectroscopy to investigate the conformational stability of flexible molecules. Multiple conformers with different CCOC dihedral angles and side-chain orientations relative to the benzene ring plane were found using quantum chemical calculations and experimental observations. Dynamics simulations and vibrational analysis confirmed the presence of one gauche conformer and two trans conformers, and it was observed that the gauche conformer exhibited higher-frequency CH(2) modes. This phenomenon was attributed to electron delocalization from non-bonding and C-O orbitals associated with the neighboring oxygen atom, which influenced the strength of the methylene C-H bond depending on the conformer.
JOURNAL OF PHYSICAL CHEMISTRY A
(2023)
Article
Chemistry, Organic
Koki Hirano, Akira Yasuda, Takahiro Sasamori, Kosei Shioji, Kentaro Okuma, Noriyoshi Nagahora
Summary: A new series of thioxanthylium trifluoromethanesulfonates has been synthesized through a trifluoromethanesulfonic-acid-induced cyclization of thioether precursors. The electronic structure of these thioxanthylium salts was determined using UV-vis absorption spectroscopy and theoretically investigated through density functional theory calculations.
Article
Biochemistry & Molecular Biology
Hidefumi Iwashita, Satoru Torii, Noriyoshi Nagahora, Munetaka Ishiyama, Kosei Shioji, Kazumi Sasamoto, Shigeomi Shimizu, Kentaro Okuma
ACS CHEMICAL BIOLOGY
(2017)
