4720-29-0Relevant academic research and scientific papers
Synthesis of N-(2-guanidinoethyl)-tetrahydrothieno[3,2-c]azepine, N-(2- guanidinoethyl)-tetrahydro-2-benzazepine and N-(2-guanidinoethyl)-tetrahydro- 1-benzazepine as analogous to antihypertensive agent guanetidine
Ravina,Ramos,Masaguer,Mera
, p. 321 - 332 (1994)
N-(2-guanidinoethyl)-tetrahydrothieno[3,2-c]azepine 10a, N-(2- guanidinoethyl)-tetrahydro-2-benzazepine 10b and N-(2-guanidinoethyl)- tetrahydro-1-benzazepine 10c analogous of the antihypertensive agent Guanetidine were prepared by cyanomethylation of the corresponding azepines, reduction and subsequent guanilation of the resulting aminoethyl derivatives. These compounds were evaluated for antihypertensive activity in SHR rats but no significant activity was observed.
Continuous reductive amination of biomass-derived molecules over carbonized filter paper-supported FeNi alloy
Chieffi, Gianpaolo,Braun, Max,Esposito, Davide
, p. 3590 - 3594 (2015)
This paper reports the continuous reductive amination of different molecules, including biomass-related compounds, over carbon-supported FeNi nanoparticles obtained on the basis of inexpensive and abundant metal precursors and cellulose. A biorefinery case study for the preparation of pyrrolidones via acid-catalyzed hydrolysis of glucose followed by reductive amination of the obtained levulinic acid is described. Burn in the fire of filters: Continuous reductive amination of biomass-derivable molecules is achieved using a carbonized filter paper-supported FeNi catalyst in combination with EtOH, MeOH, and 2-methyl THF as green solvents. A biorefinery case study for the preparation of pyrrolidones using crude levulinic acid feeds is also investigated.
Two stepwise synthetic routes toward a hetero[4]rotaxane
Luo, Qian-Fu,Zhu, Lan,Rao, Si-Jia,Li, Hong,Miao, Qi,Qu, Da-Hui
, p. 4704 - 4709 (2015)
Heterorotaxanes have been emerging as an important class of mechanically interlocked molecules and have attracted much attention in recent years. Driven by the distinguishable host-guest interactions between crown ether macrocycles and ammonium with different sizes, a novel hetero[4]rotaxane was successfully prepared by employing the combination of copper-catalyzed "click" reaction and P(n-Bu)3-catalyzed esterification reaction as stoppering reactions. The hetero[4]rotaxane contains an interlocked species in which a dibenzo[24]crown-8 ring threaded by a dibenzylammonium-containing component with two benzo[21]crown-7 macrocycles at both ends to act as stoppers, and each of the two benzo[21]crown-7 rings is also threaded with a benzylalkylammonium unit to form the second interlocked species. The hetero[4]rotaxane was prepared through two different stepwise synthetic routes, and the complicated chemical structure of the hetero[4]rotaxane was well-characterized by 1H NMR spectroscopy and high-resolution electrospray ionization (HR-ESI) mass spectrometry. The investigation shows that the construction of complicated topological heterorotaxane can be achieved via distinct approaches with high efficiencies, which may provide a foundation for the construction of more sophisticated heterorotaxane systems or functional supermolecules.
NOVEL HISTONE METHYLTRANSFERASE INHIBITORS
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Page/Page column 30; 91-92, (2021/04/01)
The present invention relates to novel compounds of formula (I) as defined herein. The compounds are inhibitors of histone methyltransferases of the seven-beta-strand family, in particular of KMT9.
An Alternative Approach to the Hydrated Imidazoline Ring Expansion (HIRE) of Diarene-Fused [1.4]Oxazepines
Grintsevich, Sergey,Sapegin, Alexander,Reutskaya, Elena,Peintner, Stefan,Erdélyi, Máté,Krasavin, Mikhail
, p. 5664 - 5676 (2020/07/21)
A four-step approach to the “hydrated imidazoline ring expansion” (HIRE) is presented. In most cases, the ring expansion was the sole process. However, for the first time, an alternative course of the hydrated imidazoline evolution was discovered which gave N-aminoethyl derivatives. These can, in principle, be converted into the target HIRE products under sufficiently forcing conditions. The approach offers improved flexibility with respect to the peripheral substituents and is also applicable to the synthesis of eleven-membered lactams. We observed that the latter can exist in two stable isomeric forms due to lactam–amide bond isomerization. The latter finding further demonstrates the value of medium-sized rings as multiple-conformer probes for biological target interrogation.
Cyclic Sulfamidite as Simultaneous Protecting Group for Amino Alcohols: Development of a Mild Deprotection Protocol Using Thiophenol
Sakata, Juri,Akita, Kazunari,Sato, Manabu,Shimomura, Masashi,Tokuyama, Hidetoshi
, p. 996 - 1000 (2020/11/03)
This study describes the novel utility of cyclic sulfamidite as a simultaneous protecting group for 1,2- or 1,3-amino alcohols. An exceptionally mild and neutral condition for the removal of the cyclic sulfamidite was developed. The deprotection condition demonstrated a broad range of functional-group compatibility, including a substrate bearing a Z-enyne structure without any loss of double-bond stereochemistry.
Iron-Catalyzed Anti-Markovnikov Hydroamination and Hydroamidation of Allylic Alcohols
Ma, Wei,Zhang, Xiaohui,Fan, Juan,Liu, Yuxuan,Tang, Weijun,Xue, Dong,Li, Chaoqun,Xiao, Jianliang,Wang, Chao
supporting information, p. 13506 - 13515 (2019/09/09)
Hydroamination allows for the direct access to synthetically important amines. Controlling the selectivity of the reaction with efficient, widely applicable, and economic catalysts remains challenging, however. This paper reports an iron-catalyzed formal anti-Markovnikov hydroamination and hydroamidation of allylic alcohols, which yields γ-amino and γ-amido alcohols, respectively. Homoallylic alcohol is also feasible. The catalytic system, consisting of a pincer Fe-PNP complex (1-4 mol %), a weak base, and a nonpolar solvent, features exclusive anti-Markovnikov selectivity, broad substrate scope (>70 examples), and good functional group tolerance. The reaction could be performed at gram scale and applied to the synthesis of drug molecules and heterocyclic compounds. When chiral substrates are used, the stereochemistry and enantiomeric excess are retained. Further application of the chemistry is seen in the functionalization of amino acids, natural products, and existing drugs. Mechanistic studies suggest that the reaction proceeds via two cooperating catalytic cycles, with the iron complex catalyzing a dehydrogenation/hydrogenation process while the amine substrate acts as an organocatalyst for the Michael addition step.
[Co(TPP)]-Catalyzed Formation of Substituted Piperidines
Lankelma, Marianne,Olivares, Astrid M.,de Bruin, Bas
, p. 5658 - 5663 (2019/04/08)
Radical cyclization via cobalt(III)-carbene radical intermediates is a powerful method for the synthesis of (hetero)cyclic structures. Building on the recently reported synthesis of five-membered N-heterocyclic pyrrolidines catalyzed by CoII porphyrins, the [Co(TPP)]-catalyzed formation of useful six-membered N-heterocyclic piperidines directly from linear aldehydes is presented herein. The piperidines were obtained in overall high yields, with linear alkenes being formed as side products in small amounts. A DFT study was performed to gain a deeper mechanistic understanding of the cobalt(II)-porphyrin-catalyzed formation of pyrrolidines, piperidines, and linear alkenes. The calculations showed that the alkenes are unlikely to be formed through an expected 1,2-hydrogen-atom transfer to the carbene carbon. Instead, the calculations were consistent with a pathway involving benzyl-radical formation followed by radical-rebound ring closure to form the piperidines. Competitive 1,5-hydrogen-atom transfer from the β-position to the benzyl radical explained the formation of linear alkenes as side products.
Preparation method of 8-tert-butyl-1-ethyl-6,7-dihydro-5H-imidazo[1,5-a][1,4]diazepine-1,8(9H)-dicarboxylic acid ester
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, (2019/12/25)
The invention relates to a preparation method of 8-tert-butyl-1-ethyl-6,7-dihydro-5H-imidazo[1,5-a][1,4]diazepine-1,8(9H)-dicarboxylic acid ester. A purpose of the present invention is to mainly solvethe technical problem that no suitable industrial synthesis method exists at present. According to the present invention, the method comprises nine steps, the synthetic route is defined in the specification, and the obtained compound can be used as the useful intermediate or product for synthesizing a plurality of medicines.
Microwave-Assisted CuCl-Catalyzed Three-Component Reactions of Alkynes, Aldehydes, and Amino Alcohols
Chen, Ning,Li, Xiang,Xu, Jiaxi
supporting information, p. 3336 - 3344 (2019/08/28)
A microwave (MW)-assisted three-component coupling of amino alcohols, aldehydes, and alkynes is developed under catalysis by CuCl. Compared with thermal conditions, MW irradiation greatly increases the reaction efficiency. The reactions of various primary N -alkyl/arylamino alcohols, aliphatic/aromatic aldehydes, and alkynes are systematically investigated, affording the desired products in moderate to good yields. Notably, acetylene is also an effective reactant under the current MW-assisted conditions.
