170697-87-7Relevant academic research and scientific papers
CAN-catalyzed vinylogous povarov reactions: The first three-component synthesis of 2-functionalized tetrahydroquinolines from anilines, cinnamaldehyde and vinyl ethers
Sridharan, Vellaisamy,Avenda?o, Carmen,Menéndez, J. Carlos
, p. 1079 - 1082 (2007)
The CAN-catalyzed reaction between anilines, cinnamaldehyde and vinyl ethers affords 2-styryl-1,2,3,4-tetrahydroquinolines. In the case of noncyclic vinyl ethers, these reactions are completely stereoselective and furnish exclusively the diastereomer with
Discovery of fused heterocyclic carboxamide derivatives as novel α7-nAChR agonists: Synthesis, preliminary SAR and biological evaluation
Xue, Yu,He, Xiaomeng,Yang, Taoyi,Wang, Yuxi,Liu, Zhenming,Zhang, Guisen,Wang, Yanxing,Wang, Kewei,Zhang, Liangren,Zhang, Lihe
, (2019/08/20)
The α7 nicotinic acetylcholine receptor (α7 nAChR) has emerged as a promising therapeutic target for schizophrenia. In our previous work, a novel series of α7-nAChR agonists bearing scaffold of indolizine were discovered. To explore the effect of aromaticity on the activity and find more active agents, herein, fused heterocyclic carboxamide derivatives were designed and synthesized in this study. Based on the evaluation by two-electrode voltage clamp in Xenopus oocytes, 27 of the synthesized compounds showed obvious agonism of α7 nAChR. Particularly, compounds 10a and 10e showed significantly higher Emax than EVP-6124. The result illustrated the importance of aromaticity to the activity of agonism. Compound 10a, which showed EC50 of 1.88 μM and Emax of 72.4%, was further characterized comprehensively, including co-application with type II positive allosteric modulator PNU-120596, selectivity with other closely related ligand-gated ion channel, etc. The results showed that 10a showed moderate selectivity over other subtypes such as α4β2 and α3β4 nAChR. 10a evoked α7-like currents that were inhibited by MLA and enhanced in the presence of the α7 PAM PNU-120596. The analysis of binding mode and understanding of structure-activity relationship provided insights to develop more potent novel α7-nAChR agonists.
High throughput one pot synthesis of 2-methylquinolines
Chandrashekarappa, Kiran Kumar H.,Mahadevan, Kittappa M.,Manjappa, Kiran B.
supporting information, p. 1368 - 1370 (2013/04/23)
Various 2-methylquinolines have been successfully synthesized by using anilines and ethyl vinyl ether in 1:3 mole ratios in the presence of acetic acid. Stirring at rt for 3-4 h followed by reflux for 3.5-4 h resulted in the corresponding 2-methylquinolines in good yield. Copyright
Convenient, two-step synthesis of 2-styrylquinolines: an application of the CAN-catalyzed vinylogous type-II Povarov reaction
Sridharan, Vellaisamy,Avenda?o, Carmen,Carlos Menéndez
experimental part, p. 2087 - 2096 (2009/07/18)
A new, experimentally simple, synthesis of 2-styrylquinolines was developed using a two-step sequence based on a CAN-catalyzed three-component type-II vinylogous Povarov reaction from arylamines, cinnamaldehydes, and electron-rich cyclic and noncyclic vin
CAN-catalyzed three-component reaction between anilines and alkyl vinyl ethers: stereoselective synthesis of 2-methyl-1,2,3,4-tetrahydroquinolines and studies on their aromatization
Sridharan, Vellaisamy,Avenda?o, Carmen,Menéndez, J. Carlos
, p. 673 - 681 (2007/10/03)
The CAN-catalyzed reaction between anilines and vinyl ethers at room temperature provides a convenient and efficient access to?4-alkoxy-2-methyl-1,2,3,4-tetrahydroquinolines. This reaction is stereoselective, favouring a cis arrangement for the alkoxy and methyl groups, and involves a three-component process that leaves a molecule of alcohol as the only side product. 2-Methylquinoline derivatives were efficiently prepared from 4-alkoxy-2-methyl-1,2,3,4-tetrahydroquinolines by Pd-C-promoted dehydrogenation.
Uncatalysed Domino Reaction in Hexafluoroisopropanol: A Simple Protocol for the Synthesis of Tetrahydroquinoline Derivatives
Di Salvo, Andrea,Spanedda, Maria Vittoria,Ourevitch, Michele,Crousse, Benoit,Bonnet-Delpon, Daniele
, p. 2231 - 2235 (2007/10/03)
A range of tetrahydroquinolines were synthesised in excellent yields through a domino reaction performed in hexafluoropropanol, starting from anilines and enol ethers and in the absence of Lewis acid catalysis. This solvent was shown to promote the nucleophilic addition of anilines to enol ethers as well as the aza-Diels-Alder reaction.
One Step Synthesis of 4-Ethoxy-1,2,3,4-Tetrahydroquinoline from Nitroarene and Ethanol: A TiO2 Mediated Photocatalytic Reaction
Park, Koon Ha,Joo, Hyun Sang,Ahn, Kyung Il,Jun, Kun
, p. 5943 - 5946 (2007/10/02)
4-Ethoxy-1,2,3,4-tetrahydroquinoline is formed in a one pot reaction from a heterogeneous solution of nitroarene, ethanol, and TiO2 by UV light (λ=350 nm).
