67848-71-9Relevant academic research and scientific papers
Process method for synthesizing N-substituted piperidine-4-boric acid
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Paragraph 0024, (2020/06/17)
The invention relates to an organic compound synthesis method, and relates to a process method for synthesizing N-substituted piperidine-4-boric acid, which comprises the following steps of: reactingN-substituted piperidine-4-alcohol used as a raw material with thionyl chloride and organic alkali in a solvent to generate N-substituted piperidine-4-chlorine, reacting the N-substituted piperidine-4-chlorine used as a raw material with lithium metal and bis (N, N-dimethylamino) borane halide in a solvent, quenching and acidifying to obtain N-substituted piperidine-4-boric acid. The process method has the advantages of originality, low cost, safety and mild reaction conditions, avoids the dangerous reaction that other patented methods adopt expensive palladium hydroxide hydrogenation, has potential cost advantage and safety advantage, and is suitable for industrial scale-up production.
A 5 + 1 Protic Acid Assisted Aza-Pummerer Approach for Synthesis of 4-Chloropiperidines from Homoallylic Amines
Ebule, Rene,Mudshinge, Sagar,Nantz, Michael H.,Mashuta, Mark S.,Hammond, Gerald B.,Xu, Bo
, p. 3249 - 3259 (2019/03/20)
We report that HCl·DMPU induces the formation of (thiomethyl)methyl carbenium ion from DMSO under mild conditions. Homoallylic amines react with this electrophile to generate 4-chloropiperidines in good yields. The method applies to both aromatic and aliphatic amines. The use of HCl·DMPU as both non-nucleophilic base and chloride source constitutes an environmentally benign alternative for piperidine formation. The reaction has a broad substrate scope, and the conditions offer good chemical yields with high functional group tolerance and scalability.
Frustrated Lewis Pair Catalyzed Hydrogenation of Amides: Halides as Active Lewis Base in the Metal-Free Hydrogen Activation
Sitte, Nikolai A.,Bursch, Markus,Grimme, Stefan,Paradies, Jan
, p. 159 - 162 (2019/01/04)
A method for the metal-free reduction of carboxylic amides using oxalyl chloride as an activating agent and hydrogen as the final reductant is introduced. The reaction proceeds via the hydrogen splitting by B(2,6-F2-C6H3)3 in combination with chloride as the Lewis base. Density functional theory calculations support the unprecedented role of halides as active Lewis base components in the frustrated Lewis pair mediated hydrogen activation. The reaction displays broad substrate scope for tertiary benzoic acid amides and α-branched carboxamides.
The effect of the structure of derivatives of nitrogen-containing heterocycles on their anti-influenza activity
Gridina, Tatyana L.,Fedchuk, Alla S.,Basok, Stephan S.,Artemenko, Anatoliy G.,Ognichenko, Liudmila N.,Shitikova, Larisa I.,Lutsyuk, Anatolii F.,Gruzevskii, Aleksandr A.,Kuz’min, Victor E.
, p. 455 - 462 (2019/06/20)
[Figure not available: see fulltext.] An adequate QSAR model based on the simplex representation of the molecular structure was built in order to optimize the search for new anti-influenza agents. Structural interpretation of the model allowed us to identify molecular fragments that determine the activity of compounds against human influenza viruses. Further virtual screening and targeted synthesis allowed us to select a group of potentially effective compounds, three of which, derivatives of piperidine and isoindoline, turned out to be the most promising.
A cascade Aza-Cope/Aza-prins cyclization leading to piperidine derivatives
Nallasivam, Jothi L.,Fernandes, Rodney A.
, p. 2012 - 2022 (2015/03/18)
The cascade aza-Cope/aza-Prins cyclization of homoallylamines to give substituted piperidines has been explored. The use of glyoxalic acid as the carbonyl component afforded bicyclic structures as a result of the internal carboxylate anion trapping the intermediate cation. The unimolecular bis-, tris-, and tetrakis(homoallylamine)s efficiently delivered the appended bis-, tris- and tetrakis(piperidine-4-ol)s (tripod and crucifix shape, respectively) as new entities. The latter compound served as an excellent ligand in the Suzuki-Miyaura cross-coupling reaction to synthesize incrustoporin. The cascade aza-Cope/aza-Prins cyclization of homoallylamines to give substituted piperidines is described. A unimolecular tetrapiperidine derivative, which resulted from this strategy, was employed as a ligand in the Suzuki-Miyaura cross-coupling reaction of an α-iodobutenolide with an arylboronic acid in an efficient synthesis of incrustoporin and its analogues.
Convenient preparation of aryl ether derivatives using a sequence of functionalized polymers
Lizarzaburu, Mike E.,Shuttleworth, Stephen J.
, p. 4873 - 4876 (2007/10/03)
A four-step synthesis to aryl ether derivatives, three of which utilize polymer-supported reagents, has been developed. Supported triphenylphosphine was successfully utilized in two distinct synthetic processes in the first step, whilst supported base and ionic and covalent scavengers were employed to complete the synthesis and purification of the target compounds.
Synthesis of Substituted Piperidines from N,N-Bis [(benzotriazol-1 -yl)methyl]amines
Katritzky, Alan R.,Luo, Zhushou,Cui, Xi-Lin
, p. 3328 - 3331 (2007/10/03)
N,N-Bis[(benzotriazol-1-yl)methyl]benzylamines and N,N-bis[(benzotriazol-1-yl)methyl](p-N′,N′-dimethylphenyl)amine on reaction with allyltrimethylsilanes yielded substituted piperidines. Other N,N-bis[(benzotriazol-1-yl)methyl]anilines (unsubstituted and p-CH3, OCH3, Cl) gave julolidines (2,3,6,7-tetrahydro-1H,5H-pyrido[3,2,1-ij] quinoline).
TiCL4 INDUCED IMINIUM ION CYCLIZATIONS OF α-CYANOAMINES
Yang, Teng-Kuei,Hung, Shun-Ming,Lee, Dong-Sheng,Hong, An-Way,Cheng, Chan-Chun
, p. 4973 - 4976 (2007/10/02)
Tertiary α-cyanoamines served as the precursors of iminium ions in the presence of titanium tetrachloride.Various intramolecular nucleophiles, olefinic and acetylenic, were found to produce cyclized products.The influences of ring sizes and substitutions on the double bonds were also investigated.
