4783-65-7Relevant academic research and scientific papers
Synthesis and lateral root-inducing activity of novel N-substituted-2-piperidones with a 1,4-benzodioxan ring
Tsukada, Hidetaka,Yamada, Naotaka,Taniguchi, Eiji,Kuwano, Eiichi
, p. 2229 - 2231 (2000)
Novel N-substituted-2-piperidones with a 1,4-benzodioxan ring were prepared and evaluated for their activity to induce lateral roots in lettuce seedlings. Compounds were obtained by aldol condensation of the lithium enolate of N-substituted-2-piperidones
η6-Arene CH?O Interaction Directed Dynamic Kinetic Resolution – Asymmetric Transfer Hydrogenation (DKR-ATH) of α-Keto/enol-Lactams
Chen, Yong,Lin, Yicao,Luo, Zhonghua,Sun, Guodong,Wang, Zhongqing,Wu, Shuming,Zhang, Lei
supporting information, p. 3030 - 3034 (2021/06/01)
A dynamic kinetic resolution – asymmetric transfer hydrogenation (DKR-ATH) methodology of α-keto/enol-lactams was developed. We also propose a possible catalytic mechanism evolving a transition state stabilized by η6-arene CH?O interaction. The efficient approach can be applied to a wide range of substrates including non-aryl ones which would be difficult to prepare by other asymmetric reduction methods. (Figure presented.).
Synthesis of Lactams by Reductive Amination of Carbonyl Derivatives with ω-Amino Fatty Acids under Hydrosilylation Conditions
Tongdee, Satawat,Wei, Duo,Wu, Jiajun,Netkaew, Chakkrit,Darcel, Christophe
supporting information, p. 5536 - 5539 (2021/08/07)
An efficient method for the preparation of lactams from ω-amino fatty acids under hydrosilylation is described. A variety of lactams such as pyrrolidinones, piperidinones and 2-azepanones were selectively synthesised in moderate to excellent yields (29 examples, up to 95 % isolated yields) with a good functional group tolerance. Notably, no metallic based catalyst was required to perform this transformation.
Transition-Metal-Free Reductive Functionalization of Tertiary Carboxamides and Lactams for α-Branched Amine Synthesis
Chiba, Shunsuke,Dixon, Darren J.,Fan, Dongyang,Ong, Derek Yiren
supporting information, p. 11903 - 11907 (2020/05/22)
A new method for the synthesis of α-branched amines by reductive functionalization of tertiary carboxamides and lactams is described. The process relies on the efficient and controlled reduction of tertiary amides by a sodium hydride/sodium iodide composite, in situ treatment of the resulting anionic hemiaminal with trimethylsilyl chloride and subsequent coupling with nucleophilic reagents including Grignard reagents and tetrabutylammonium cyanide. The new method exhibits broad functional-group compatibility, operates under transition-metal-free reaction conditions, and is suitable for various synthetic applications on both sub-millimole and on multigram scales.
Solvent-free iron(III) chloride-catalyzed direct amidation of esters
Mkhonazi, Blessing D.,Shandu, Malibongwe,Tshinavhe, Ronewa,Simelane, Sandile B.,Moshapo, Paseka T.
supporting information, (2020/03/17)
Amide functional groups are prominent in a broad range of organic compounds with diverse beneficial applications. In this work, we report the synthesis of these functional groups via an iron(iii) chloride-catalyzed direct amidation of esters. The reactions are conducted under solvent-free conditions and found to be compatible with a range of amine and ester substrates generating the desired amides in short reaction times and good to excellent yields at a catalyst loading of 15 mol%.
A Unified Strategy for the Synthesis of Difluoromethyl- And Vinylfluoride-Containing Scaffolds
Duchemin, Nicolas,Buccafusca, Roberto,Daumas, Marc,Ferey, Vincent,Arseniyadis, Stellios
supporting information, p. 8205 - 8210 (2019/10/16)
Here, we report a general method for the synthesis of quaternary and tertiary difluoromethylated compounds and their vinylfluoride analogues. The strategy, which relies on a two-step sequence featuring a C-selective electrophilic difluoromethylation and either a palladium-catalyzed decarboxylative protonation or a Krapcho decarboxylation, is practical, scalable, and high yielding. Considering the generality of the method and the attractive properties offered by the difluoromethyl group, this approach provides a valuable tool for late-stage functionalization and drug development.
Iron-Catalysed Reductive Amination of Carbonyl Derivatives with Ω-Amino Fatty Acids to Access Cyclic Amines
Wei, Duo,Netkaew, Chakkrit,Carré, Victor,Darcel, Christophe
, p. 3008 - 3012 (2019/05/15)
An efficient method for the reductive amination of carbonyl derivatives with ω-amino fatty acids catalysed by an iron complex Fe(CO)4(IMes) [IMes=1,3-bis(2,4,6-trimethylphenyl)imidazol-2-ylidene] by means of hydrosilylation was developed. A variety of pyrrolidines, piperidines and azepanes were selectively synthesised in moderate-to-excellent yields (36 examples, 47–97 % isolated yield) with a good functional group tolerance.
Palladium-Catalyzed Hydrocarbonylative C-N Coupling of Alkenes with Amides
Zhou, Xibing,Zhang, Guoying,Gao, Bao,Huang, Hanmin
supporting information, p. 2208 - 2212 (2018/04/30)
An efficient palladium-catalyzed hydrocarbonylative C-N coupling of alkenes with amides has been developed. The reaction was performed via hydrocarbonylation of alkenes, followed by acyl metathesis with amides. Both intermolecular and intramolecular react
C(sp3)-H dehydrogenation and C(sp2)-H alkoxy carbonylation of inactivated cyclic amines towards functionalized N-heterocycles
He, Yan,Wang, Fang,Zhang, Xinying,Fan, Xuesen
supporting information, p. 4002 - 4005 (2017/04/11)
A novel and efficient synthesis of tetrahydropyridine (THP)-, dihydropyrrole (DHP)-, or tetrahydroazepine (THA)-3-carboxylates via cascade reactions of inactivated cyclic amines with CO and alcohols is presented. To our knowledge, this should be the first
Transition-Metal-Free Amine Oxidation: A Chemoselective Strategy for the Late-Stage Formation of Lactams
Griffiths, Robert J.,Burley, Glenn A.,Talbot, Eric P. A.
supporting information, p. 870 - 873 (2017/02/26)
A metal-free strategy for the formation of lactams via selective oxidation of cyclic secondary and tertiary amines is described. Molecular iodine facilitates both chemoselective and regioselective oxidation of C-H bonds directly adjacent to a cyclic amine. The mild conditions, functional group tolerance, and substrate scope are demonstrated using a suite of diverse small molecule cyclic amines, including clinically approved drug scaffolds.
