Review
Chemistry, Multidisciplinary
Risto Savela, Carolina Mendez-Galvez
Summary: Isoindolinone structure is an important privileged scaffold found in a large variety of naturally occurring as well as synthetic, biologically and pharmaceutically active compounds. Synthetic methodologies for accessing this heterocyclic skeleton have received significant attention during the past decade, with two main categories of strategies identified.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Organic
Xiao-Qiang Hu, Zi-Kui Liu, Ye-Xing Hou, Ji-Hang Xu, Yang Gao
Summary: The study reports the first merger of strain-release of 1,2-oxazetidines with carboxylic acid directed C-H activation in catalytic synthesis of isoindolinones, providing a new sustainable pathway for preparing diverse isoindolinone skeletons and demonstrating great synthetic potential in drug discovery. Mechanistic studies revealed a plausible C-H activation/beta-carbon elimination/intra-molecular cyclization cascade pathway.
Article
Chemistry, Multidisciplinary
Yong Wu, Li Zeng, Haoran Li, Yue Cao, Jingcheng Hu, Minghao Xu, Renyi Shi, Hong Yi, Aiwen Lei
Summary: The paper presents an electrochemical palladium-catalyzed method for oxidative carbonylation, avoiding the hazardous mixing of CO with oxygen. This approach provides a diverse array of ynones and can serve as an alternative to the carbonylative Sonogashira reaction.
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2021)
Article
Chemistry, Multidisciplinary
Janos T. Csenki, Balazs L. Toth, Ferenc Beke, Balint Varga, Peter P. Feher, Andras Stirling, Zsuzsanna Czegeny, Attila Benyei, Zoltan Novak
Summary: This study reports a novel dyotropic rearrangement process involving the migration of iodine atoms in alkyl fragments, demonstrated through experimental and DFT studies. A new fluoroalkyl iodonium reagent was designed and synthesized using the dyotropic rearrangement, showing excellent fluoroalkylation activity towards various amines and nitrogen heterocycles.
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
(2022)
Article
Chemistry, Organic
Jiaqi Yan, Yongzheng Ding, Hanmin Huang
Summary: A palladium-catalyzed carbonylative cyclization reaction of ortho-bromoarylimines is reported, allowing for the chemodivergent synthesis of functionalized biisoindolinones and spirocyclic isoindolinones. By switching the reaction temperatures and ligands, either product could be selectively obtained, and the biisoindolinone products could be easily achieved with catalyst loadings as low as 0.05 mol%. Further transformation of the biisoindolinone product is also described, providing a novel and concise approach to the biisoindoline diamine ligand.
JOURNAL OF ORGANIC CHEMISTRY
(2023)
Article
Chemistry, Organic
Lona Dutta, Anwita Chattopadhyay, Nisha Yadav, S. S. V. Ramasastry
Summary: This study presents a metal-free strategy for the synthesis of various alpha-arylidene cyclopenta[b]indoles by phosphine-catalysed (3 + 2) annulation of alpha,beta-ynones and 3-nitroindoles. The rearomatisation of the indole nucleus was observed for the first time during this annulative transformation. The method was also applied to the synthesis of an antimalarial natural product, bruceolline E.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2023)
Article
Chemistry, Multidisciplinary
Rui Fu, Yu Liu, Tao Wu, Xinyu Zhang, Yang Zhu, Jiangbin Luo, Zhengyu Zhang, Yaojia Jiang
Summary: This study presents a cascade method for the synthesis of beta-aminoketones through the reductive hydroamination of alkynes under mild metal-free conditions. The method offers a rapid and diverse approach for the synthesis of drug molecules with the beta-aminoketone skeleton.
CHEMICAL COMMUNICATIONS
(2022)
Article
Chemistry, Organic
Subin Yoon, Sungbin Lee, Seung Hyun Nam, Hyejeong Lee, Yunmi Lee
Summary: This study presents an efficient and mild method for the synthesis of cyclic beta-amino ketones containing N-substituted quaternary carbon centers through the aza-Michael addition reaction of pyrazoles to beta-substituted cyclic alpha,beta-enones catalyzed by KOt-Bu. A wide range of new and versatile beta-pyrazolyl ketones were obtained in good yields. Additionally, the KOt-Bu-catalyzed one-pot diamination of a cyclic dienone with pyrazoles via aza-1,6-conjugate addition followed by aza-1,4-conjugate addition was explored.
ORGANIC & BIOMOLECULAR CHEMISTRY
(2022)
Article
Chemistry, Organic
Guang-Xin Ru, Meng Zhang, Ting-Ting Zhang, Xiao-Lei Jiang, Guang-Qin Gao, Xiu-Hong Zhu, Shun Wang, Cai-Ling Fan, Xiao Li, Wen-Bo Shen
Summary: This study presents a novel copper-catalyzed reaction for the efficient synthesis of diverse spiroindoles with various functional groups. It also demonstrates the successful construction of challenging carbon-carbon bonds and alkenes.
ORGANIC CHEMISTRY FRONTIERS
(2022)
Article
Chemistry, Organic
Bin Sun, Pei-Xuan Li, Yu Jiang, Lu-Lu Yang, Pan-Yi Huang, Run-Pu Shen, Mao-Jie Chen, Jia-Yang Wang, Can Jin
Summary: A visible-light-driven desaturative beta-alkoxyoxalyation reaction has been reported. The reaction proceeds under mild conditions and does not require a photocatalyst or transition metal. The C-Br bond undergoes homolysis to produce a difluoroalkyl radical, which then undergoes defluorinated beta-alkoxyoxalylation cascades to yield a wide range of beta-ketoester/ketoamide substituted enamines. The oxygen source for the carbonyl unit is confirmed to be H2O through O-18 labeling experiments.
Article
Chemistry, Multidisciplinary
Ana Koperniku, Laurel L. Schafer
Summary: The zirconium catalyzed hydroaminoalkylation of alkenes with N-aryl- and sterically demanding N-alkyl-alpha-arylated secondary amines using commercially available Zr(NMe2)(4) is reported. The catalyst is compatible with challenging alpha-heteroarylated amines and functionalized alkene substrates, providing a new disconnection strategy for selectively substituted saturated alpha-arylated heterocycles.
CHEMISTRY-A EUROPEAN JOURNAL
(2021)
Article
Chemistry, Organic
Chungang Li, Mingli Zhong, Zheng Zeng, Yiqiu Deng, Lanyu Li
Summary: An iridium-catalyzed hydrogen transfer strategy allows for the straightforward synthesis of tetrahydropyridine derivatives, offering high efficiency and environmental friendliness.
JOURNAL OF ORGANIC CHEMISTRY
(2022)
Article
Chemistry, Multidisciplinary
Jokin Diaz de Sarralde, Elene Astobieta, Ania Sevilla, Yuliet Rincon, Maria Teresa Herrero, Garazi Urgoitia, Raul SanMartin
Summary: With the scarcity of chemical resources, catalysis by first-row transition metals has gained increasing interest. Iron, due to its abundance, low toxicity, and unique electronic features, holds promise. In this study, quinazoline alkaloids were synthesized from alkynoic acids and functionalized amines using iron dibromide and pyridine as catalysts in toluene or a solventless reaction system. The study focused on iron sources, reaction media, and the effect of additives. Results showed high yields and regioselective preparation of nitrogen- and oxygen-containing scaffolds. This is the first example of a cascade process involving alkynoic acids catalyzed by iron. Compared to previously reported gold, copper, and ruthenium catalysts for similar transformations, iron is more abundant, cheaper, and less toxic.
ENVIRONMENTAL CHEMISTRY LETTERS
(2022)
Article
Chemistry, Multidisciplinary
Changqu Lin, Hao Yang, Xin Gao, Yue Zhuang, Caojian Feng, Hongli Wu, Haifeng Gan, Fei Cao, Ping Wei, Pingkai Ouyang
Summary: In this study, a process for the selective conversion of N-acetyl-D-glucosamine (NAG) into unsubstituted 3-acetamidofuran (3AF) is developed. The yield of 3AF from NAG catalyzed by a ternary Ba-(OH)(2)-H3BO3-NaCl catalytic system in N-methylpyrrolidone at 180 degrees C for 20 min can reach 73.9%. Mechanistic studies reveal that the pathway to 3AF starts with a base-promoted retro-aldol condensation of the ring-opened NAG, affording the key intermediate N-acetylerythrosamine.
Article
Chemistry, Organic
Bastian L. Springer, Kristina Holzschneider, Fabian Mohr, Stefan F. Kirsch
Summary: A new synthetic route for phenanthro[9,10-d]imidazoles is reported. The target compounds were synthesized through the aminolysis of readily accessible 10,10-diazidophenanthren-9(10H)-one with nucleophilic amines, followed by a self-condensation. X-ray single crystallography was used to determine the molecular structures, and the optical properties of the material were described.
SYNTHESIS-STUTTGART
(2023)
Article
Chemistry, Multidisciplinary
Ziping Cao, Hongbo Zhu, Xin Meng, Laijin Tian, Xuejun Sun, Guang Chen, Jinmao You
CHEMISTRY-A EUROPEAN JOURNAL
(2016)
Article
Chemistry, Organic
Ziping Cao, Hongbo Zhu, Xin Meng, Laijin Tian, Guang Chen, Xuejun Sun, Jinmao You
JOURNAL OF ORGANIC CHEMISTRY
(2016)
Article
Chemistry, Organic
Rumeng Zhang, Hongbo Zhu, Xin Meng, Ziping Cao, Guang Chen, Laijin Tian, Xuejun Sun, Jinmao You
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2017)
Article
Chemistry, Organic
Hongbo Zhu, Xin Meng, Yanhui Zhang, Guang Chen, Ziping Cao, Xuejun Sun, Jinmao You
JOURNAL OF ORGANIC CHEMISTRY
(2017)
Article
Chemistry, Organic
Xin Meng, Hongbo Zhu, Guang Chen, Laijin Tian, Xuejun Sun, Ziping Cao, Jinmao You
ASIAN JOURNAL OF ORGANIC CHEMISTRY
(2017)
Article
Chemistry, Organic
Yulei Zhao, Zheng Zhang, Xu Liu, Zongkang Wang, Ziping Cao, Laijin Tian, Mingbo Yue, Jinmao You
JOURNAL OF ORGANIC CHEMISTRY
(2019)
Article
Chemistry, Organic
Xin Meng, Minghui Guo, Jiekun Zhu, Hongbo Zhu, Xuejun Sun, Laijin Tian, Ziping Cao
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
(2019)
Article
Chemistry, Organic
Ziping Cao, Jiekun Zhu, Li Liu, Yuanling Pang, Laijin Tian, Xuejun Sun, Xin Meng
BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY
(2019)
Article
Chemistry, Multidisciplinary
Ziping Cao, Changyin Zhao, Jiekun Zhu, Shikun Yan, Laijin Tian, Xuejun Sun, Xin Meng
Article
Chemistry, Multidisciplinary
Hong Jiang, Wenqiang Zhang, Xing Kang, Ziping Cao, Xu Chen, Yan Liu, Yong Cui
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
(2020)
Article
Chemistry, Multidisciplinary
Jun Qu, Qing Zhang, Xiaoming Liao, Cunyu Song, Xin Meng, Yuanchun He, Zan Li, Xiaoxiang Zhang, Ziping Cao
Summary: In this study, two new organic molecules were designed and synthesized, which exhibit excellent fluorescence emissions with tunable dual emission bands in both solution and solid states. The water fraction in THF was found to have an effect on the tuning of emission bands. Additionally, the potential application of these molecules in anti-counterfeiting ink was explored.
CHEMISTRY-A EUROPEAN JOURNAL
(2023)
Article
Chemistry, Multidisciplinary
Minghui Guo, Xin Meng, Yang Zhao, Yuexia Dong, Xuejun Sun, Laijin Tian, Ziping Cao
Article
Chemistry, Analytical
Guang Chen, Qiang Fu, Fabiao Yu, Rui Ren, Yuxia Liu, Ziping Cao, Guoliang Li, Xianen Zhao, Lingxin Chen, Hua Wang, Jinmao You
ANALYTICAL CHEMISTRY
(2017)