24668-03-9Relevant academic research and scientific papers
Organocatalyzed aerobic oxidative Robinson-type annulation of 2-isocyanochalcones: expedient synthesis of phenanthridines
Hu, Zhongyan,Dong, Jinhuan,Men, Yang,Li, Yifei,Xu, Xianxiu
, p. 1739 - 1742 (2017)
A DBU-catalyzed aerobic oxidative Robinson annulation of 2-isocyanochalcones with active methylene ketones was developed for the expedient synthesis of phenanthridines in high to excellent yields. This unprecedented multistep domino reaction represents a
Tandem synthesis of tetrahydroquinolines and identification of the reaction network byoperandoNMR
Chen, Jingwen,Qi, Long,Zhang, Biying,Chen, Minda,Kobayashi, Takeshi,Bao, Zongbi,Yang, Qiwei,Ren, Qilong,Huang, Wenyu,Zhang, Zhiguo
, p. 4332 - 4341 (2021/07/12)
The study of the reaction mechanism and complex network for heterogeneously catalyzed tandem reactions is challenging but can guide reaction design and optimization. Here, we describe a case study using bifunctional metal-organic framework supported Pd nanoparticles (Pd/UiO-66(HCl)) for the one-pot tandem synthesis of substituted tetrahydroquinolinesviathe Claisen-Schmidt condensation and reductive intramolecular cyclization. The directly observed evolution of intermediates and products, including reactive species containing hydroxylamine group and unstable intermediate 2-phenyl-3,4-dihydroquinoline, was enabled byoperandomagic angle spinning nuclear magnetic resonance studies under 50 bar H2. The reaction network of the tandem reaction is deduced based on reaction kinetic information obtained from theoperandostudy. The optimized procedure was applied to various acetophenone and nitrobenzaldehyde derivatives carrying different functional groups, and eight valuable substituted tetrahydroquinolines were obtained in moderate to good yields. This work provides a molecular-level understanding of the catalytic system and brings up new opportunities for efficient and sustainable synthesis of medicinally relevant building blocks.
Visible-Light Induction/Br?nsted Acid Catalysis in Relay for the Enantioselective Synthesis of Tetrahydroquinolines
Xiong, Wenhui,Li, Shan,Fu, Bo,Wang, Jinping,Wang, Qiu-An,Yang, Wen
supporting information, p. 4173 - 4176 (2019/06/07)
An efficient method merging Br?nsted acid catalysis with visible-light induction for the highly enantioselective synthesis of tetrahydroquinolines has been developed. This mild process directly transforms 2-aminoenones into 2-substituted tetrahydroquinolines with excellent enantioselectivities through a relay visible-light-induced cyclization/chiral phosphoric acid-catalyzed transfer hydrogenation reaction.
Redox-Neutral Access to Sultams from 2-Nitrochalcones and Sulfur with Complete Atom Economy
Nguyen, Thanh Binh,Retailleau, Pascal
supporting information, p. 3879 - 3882 (2017/07/26)
A catalyst-free, redox-neutral, and completely atom-economical synthesis of sultams by simply heating 2-nitrochalcones with elemental sulfur in 3-picoline or N-methylmorpholine is described. The S-N, C-S, and S=O bonds of the sulfonamide are efficiently f
Effect of ring A and ring B substitution on the cytotoxic potential of pyrazole tethered chalcones
Nepali, Kunal,Kadian, Kanika,Ojha, Ritu,Dhiman, Rajni,Garg, Atul,Singh, Gagandip,Buddhiraja, Abhishek,Bedi, Preet Mohinder Singh,Dhar, Kanaya Lal
, p. 2990 - 2997 (2012/10/29)
Chalcone is an aromatic ketone that forms the central core for a variety of important biological compounds, which are collectively known as chalcones. The cytotoxic potential of chalcones which consists of C6-C 3-C6 units gets enhanced by the incorporation of pyrazole ring as proved by our earlier studies. Thus in the present work, pyrazoles of chalcones with ring A substituted by furan, naphthalene and variety of substituted phenyl rings has been prepared and evaluated for in vitro cytotoxic activity against PC-3, OVCAR, IMR-32, HEP-2 human cancer cell lines. Springer Science+Business Media, LLC 2011.
Selective reduction of nitroarenes by a Hantzsch 1,4-dihydropyridine: A facile and efficient approach to substituted quinolines
Xing, Rui-Guang,Li, Ya-Nan,Liu, Qiang,Han, Yi-Feng,Wei, Xia,Li, Jing,Zhou, Bo
experimental part, p. 2066 - 2072 (2011/08/05)
An efficient reductive cyclization of o-nitrocinnamoyl compounds was achieved by employing a Hantzsch 1,4-dihydropyridine ester as a biomimetic reducing agent in the presence of catalytic palladium on carbon. This approach was successfully applied to the synthesis of substituted quinolines. Georg Thieme Verlag Stuttgart ? New York.
