144688-69-7Relevant articles and documents
Paired Electrochemical Reactions and the On-Site Generation of a Chemical Reagent
Wu, Tiandi,Nguyen, Bichlien H.,Daugherty, Michael C.,Moeller, Kevin D.
, p. 3562 - 3565 (2019)
While the majority of reported paired electrochemical reactions involve carefully matched cathodic and anodic reactions, the precise matching of half reactions in an electrolysis cell is not generally necessary. During a constant current electrolysis almost any oxidation and reduction reaction can be paired, and in the presented work we capitalize on this observation by examining the coupling of anodic oxidation reactions with the production of hydrogen gas for use as a reagent in remote, Pd-catalyzed hydrogenation and hydrogenolysis reactions. To this end, an alcohol oxidation, an oxidative condensation, intramolecular anodic olefin coupling reactions, an amide oxidation, and a mediated oxidation were all shown to be compatible with the generation and use of hydrogen gas at the cathode. This pairing of an electrolysis reaction with the production of a chemical reagent or substrate has the potential to greatly expand the use of more energy efficient paired electrochemical reactions.
Parallel electrosynthesis of N-acyliminium ion equivalents using silica gel-supported piperidine
Tajima, Toshiki,Nakajima, Atsushi
, p. 160 - 161 (2009)
Parallel anodic methoxylation of carbamates was successfully carried out to provide the corresponding α-methoxylated products as N-acyliminium ion equivalents in high to excellent yields using silica gel-supported piperidine (Si-piperidine). Copyright
Expedient preparation of nazlinine and a small library of indole alkaloids using flow electrochemistry as an enabling technology
Kabeshov, Mikhail A.,Musio, Biagia,Murray, Philip R.D.,Browne, Duncan L.,Ley, Steven V.
supporting information, p. 4618 - 4621 (2015/01/08)
An expedient synthesis of the indole alkaloid nazlinine is reported. Judicious choice of flow electrochemistry as an enabling technology has permitted the rapid generation of a small library of unnatural relatives of this biologically active molecule. Furthermore, by conducting the key electrochemical Shono oxidation in a flow cell, the loading of electrolyte can be significantly reduced to 20 mol % while maintaining a stable, broadly applicable process.
Design, synthesis, antiviral activity, and structure-activity relationships (SARs) of two types of structurally novel phenanthroindo/quinolizidine analogues
Su, Bo,Chen, Fazhong,Wang, Lizhong,Wang, Qingmin
, p. 1233 - 1239 (2014/03/21)
To investigate the influence of the variation of the original skeletons of natural phenanthroindo/quinolizidine alkaloids on antiviral activities, two types of structurally totally novel analogues 7a, 7b, 16a, and 16b were designed, synthesized, and evaluated against tobacco mosaic virus (TMV) for the first time. Bioassay results indicated that all four of the newly designed analogues showed good to excellent antiviral activities, among which analogue 16a dispalyed comparable activity with that of ningnanmycin, perhaps one of the most successful commercial antiviral agents, thus emerging as a potential inhibitor of plant virus and serving as a new lead for further optimization. Further structure-activity relationships are also discussed, demonstrating for the first time that the same changes of the original skeletons of phenanthroindolizidine and phenanthroquinolizidine exihibted totally different antiviral activities results, providing some original and useful information about the preferential conformation for maintaining high activities.
Reactions of iminium ions with Michael acceptors through a Morita-Baylis-Hillman-type reaction: Enantiocontrol and applications in synthesis
Myers, Eddie L.,De Vries, Johannes G.,Aggarwal, Varinder K.
, p. 1893 - 1896 (2008/03/12)
(Chemical Equation Presented) All adducts one way: Iminium ions, generated in situ from the corresponding N,O-acetals, can be used as electrophiles in a Morita-Baylis-Hillman-type reaction with a wide range of Michael acceptors (enones, enals, S- and O-acrylates). The reaction has been rendered asymmetric using sulfide 1 (see scheme; DBU = 1,8-diazabicyclo[5.4.0]undec-7-ene, TMSOTf=trimethylsilyl trifluoromethanesulfonate).
Development of a novel environmentally friendly electrolytic system by using recyclable solid-supported bases for in situ generation of a supporting electrolyte from methanol as a solvent: Application for Anodic methoxylation of organic compounds
Tajima, Toshiki,Fuchigami, Toshio
, p. 6192 - 6196 (2007/10/03)
We have successfully developed a novel environmentally friendly electrolytic system using recyclable solid-supported bases for in situ generation of a supporting electrolyte from methanol as a solvent. It was found that solid-supported bases are electrochemically inactive at an electrode surface. It was also found that solid-supported bases dissociate methanol into methoxide anions and protons. Therefore, in the presence of solid-supported bases, it was clarified that methanol serves as both a solvent and a supporting electrolyte generated in situ. Anodic methoxylation of various compounds with solid-supported bases was carried out to provide the corresponding methoxylated products in good to excellent yields with a few exceptions. The methoxylated products and the solid-supported bases were easily separated by only filtration, and the desired pure methoxylated products were readily isolated simply by concentration of the filtrates. The separated and recovered solid-supported bases were recyclable for several times.
Synthesis of new trialkylsilylmethyloxazinones via intramolecular trapping of β-silyl carbocations by an N-Boc group
Brocherieux-Lanoy, Sylvie,Dhimane, Hamid,Poupon, Jean-Christophe,Vanucci, Corinne,Lhommet, Gerard
, p. 2163 - 2165 (2007/10/03)
N-BoC amino ethers 1a-e when treated with allyltrialkylsilanes in the presence of TiCl4 afford the expected allylation compounds 2a-e and/or the unprecedented silylated oxazinones 3a-e or 4a-e.
Electroorganic chemistry 139. Electroreductive decyanation of nitriles and its application to synthesis of α-alkylamines
Shono, Tatsuya,Terauchi, Jun,Kitayama, Kenji,Takeshima, Yo-Ichiro,Masumura, Yoshihiro
, p. 8253 - 8262 (2007/10/02)
Electroreduction of nitriles gave the corresponding decyanated products when Zn was used as the material of cathode in aprotic solvent (DMF or MeCN) containing Et4NOTs as a supporting electrolyte. Alkylation of amines at the α-position was effectively achieved by cyanation of amines at the α-position, and α-alkylation of the resultant α-amino nitriles followed by the electroreductive decyanation.
