3169-58-2Relevant academic research and scientific papers
Synthesis of 1-Amino-2,2,2-trifluoroalkylphosphonates from Alkene-Tethered Trifluoroacetimidoyl Chlorides
Rodríguez, José F.,Zhang, Anji,Arora, Ramon,Lautens, Mark
, p. 7540 - 7544 (2021/10/12)
The reaction of alkene-tethered trifluoroacetimidoyl chlorides with trialkyl phosphites furnishes 1-amino-2,2,2-trifluoroalkylphosphonates. The products were generated in moderate to good yields, and the scalability of this process was showcased. Partial hydrolysis of the phosphonate moiety was achieved. The cyclization is proposed to occur via formation of an imidoyl phosphonate intermediate that becomes susceptible to nucleophilic attack at nitrogen through the strong electron-withdrawing groups at the imidoyl carbon.
A heterogeneous catalytic and solvent-free approach to 1,2-dihydroquinoline derivatives from aromatic amines and alkynes by tandem hydroarylation-hydroamination
Amrutham, Vasu,Agliullin, Marat Radikovich,Mameda, Naresh,Gajula, Krishna Sai,Grigor'eva, Nellya Gennadievna,Kutepov, Boris Ivanovich,Akula, Venugopal,Nama, Narender
, (2019/11/13)
This study describes a mesoporous aluminosilicate (ASM) catalyst-induced one-step synthesis of substituted dihydroquinolines through a hydroarylation/hydroamination cascade reaction under solvent-free conditions. A sol-gel method was utilized to prepare t
Enantioselective Copper-Catalyzed Borylative Cyclization with Cyclic Imides
Whyte, Andrew,Torelli, Alexa,Mirabi, Bijan,Lautens, Mark
supporting information, p. 8373 - 8377 (2019/10/14)
An enantioselective borylative cyclization cascade utilizing cyclic imides has been developed. We employ a highly enantioselective borylcupration process that includes a 1,2-addition to a cyclic imide. The products contain a valuable hemiaminal and boronate handle for further elaborations within a congested framework. This work demonstrates the utility of cyclic imides as simple precursors to unlock access to sought-after polycyclic indolines. Futhermore, this report highlights the capability to harness reactive catalytic intermediates to exploit otherwise unreactive functional groups.
Base-catalyzed thio-lactamization of 2-(1-arylvinyl)anilines with CS2 for the synthesis of quinoline-2-thiones
Wang, Tong-Lin,Liu, Xiao-Jun,Huo, Cong-De,Wang, Xi-Cun,Quan, Zheng-Jun
supporting information, p. 499 - 502 (2018/01/19)
Here we show that the base-catalyzed thio-lactamization of 2-(1-arylvinyl)anilines with CS2 is a powerful methodology to synthesize quinoline-2-thiones. This thio-lactamization uses inexpensive and versatile 2-(1-arylvinyl)anilines, which are easily available from the reaction of amines and alkynes. Compared to the known strategy in the literature, this method features the advantages like a short synthesis step and easily available starting materials.
Base-controlled chemoselectivity reaction of vinylanilines with isothiocyanates for synthesis of quinolino-2-thione and 2-aminoquinoline derivatives
Zhang, Xi,Wang, Tong-Lin,Huo, Cong-De,Wang, Xi-Cun,Quan, Zheng-Jun
supporting information, p. 3114 - 3117 (2018/03/28)
Here, we report a base-controlled chemo-selective reaction of vinylanilines with alkyl/aryl isothiocyanates to afford quinolino-2-thione and 2-aminoquinoline derivatives. The quinolino-2-thiones could be obtained in high yields in the presence of Et3N. Particularly interesting is that the reaction could produce the 2-aminoquinolines in the presence of K3PO4 with high selectivity.
