4775-98-8Relevant academic research and scientific papers
Production of Piperidine and δ-Lactam Chemicals from Biomass-Derived Triacetic Acid Lactone
Chen, Bingfeng,Xie, Zhenbing,Peng, Fangfang,Li, Shaopeng,Yang, Junjuan,Wu, Tianbin,Fan, Honglei,Zhang, Zhaofu,Hou, Minqiang,Li, Shumu,Liu, Huizhen,Han, Buxing
supporting information, p. 14405 - 14409 (2021/05/21)
Piperidine and δ-Lactam chemicals have wide application, which are currently produced from fossil resource in industry. Production of this kind of chemicals from lignocellulosic biomass is of great importance, but is challenging and the reported routes gi
Interrupted Pyridine Hydrogenation: Asymmetric Synthesis of δ-Lactams
Wagener, Tobias,Lückemeier, Lukas,Daniliuc, Constantin G.,Glorius, Frank
supporting information, p. 6425 - 6429 (2021/02/22)
Metal-catalyzed hydrogenation is an effective method to transform readily available arenes into saturated motifs, however, current hydrogenation strategies are limited to the formation of C?H and N?H bonds. The stepwise addition of hydrogen yields reactive unsaturated intermediates that are rapidly reduced. In contrast, the interruption of complete hydrogenation by further functionalization of unsaturated intermediates offers great potential for increasing chemical complexity in a single reaction step. Overcoming the tenet of full reduction in arene hydrogenation has been seldom demonstrated. In this work we report the synthesis of sought-after, enantioenriched δ-lactams from oxazolidinone-substituted pyridines and water by an interrupted hydrogenation mechanism.
Method for synthesizing lactam derivative without catalyst
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Paragraph 0038-0041, (2019/07/10)
The invention discloses a simple synthesis method for a lactam derivative. The method comprises the step that with formamide as an amine source and a hydrogen donor (hydrolyzed to produce formic acid)and keto acid as raw materials, the lactam derivative is easily synthesized through a cycloamination reaction without a solvent or a catalyst. Compared with previous reports, the time required for the reaction is greatly shortened, the selectivity is remarkably improved, the conversion rate of the keto acid derivative is 99%, and the yield of the lactam derivative can reach 70-94%.
A Facile Direct Route to N-(Un)substituted Lactams by Cycloamination of Oxocarboxylic Acids without External Hydrogen
Li, Hu,Wu, Hongguo,Zhang, Heng,Su, Yaqiong,Yang, Song,Hensen, Emiel J. M.
, p. 3778 - 3784 (2019/08/07)
Lactams are privileged in bioactive natural products and pharmaceutical agents and widely featured in functional materials. This study presents a novel versatile approach to the direct synthesis of lactams from oxocarboxylic acids without catalyst or external hydrogen. The method involves the in situ release of formic acid from formamides induced by water to facilitate efficient cycloamination. Water also suppresses the formation of byproducts. This unconventional pathway is elucidated by a combination of model experiments and density functional theory calculations, whereby cyclic imines (5-methyl-3,4-dihydro-2-pyrrolone and its tautomeric structures) are found to be favorable intermediates toward lactam formation, in contrast to the conventional approach encompassing cascade reductive amination and cyclization. This sustainable and simple protocol is broadly applicable for the efficient production of various N-unsubstituted and N-substituted lactams.
Benzimidazole derivatives, preparation methods and uses theirof
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, (2018/12/01)
The present invention relates to benzimidazole compounds useful in treating for protein kinase-associated disorders. There is also a need for compounds useful in the treatment or prevention of one or more symptoms of cancer, transplant rejections. Furthermore, there is a need for methods for modulating the activity of protein kinases, such as CDK4 and/or CDK6, using the compounds provided herein.
An Efficient Two-Step Preparation of α-, β-, γ- or δ-Amino Acids from 2-Pyrazinones, 2-Hydroxypyrimidines or 2-Pyridones Respectively
Zacharie, Boulos,Abbott, Shaun D.,Baigent, Christopher B.,Doyle, Christopher,Yalagala, Ravi Shekar
, p. 6486 - 6493 (2018/11/23)
A practical and efficient two-step procedure is reported for the preparation of a variety of α-, β-, γ- and δ-amino acids from 2-pyridone, 2-pyrazinone or 2-hydroxypyrimidine and derivatives. The procedure is amenable to scale-up and in most cases no chromatographic purification of the product is required. This approach is useful, especially in the synthesis of amino acids or deuterated amino acids that are not obtained by other methods.
Synthesis and Antimicrobial Evaluation of Fire Ant Venom Alkaloid Based 2-Methyl-6-alkyl-Δ1,6-piperideines
Yan, Yujie,An, Yu,Wang, Xiaozhong,Chen, Yingqi,Jacob, Melissa R.,Tekwani, Babu L.,Dai, Liyan,Li, Xing-Cong
, p. 2795 - 2798 (2017/11/06)
The first synthesis of 2-methyl-6-pentadecyl-Δ1,6-piperideine (1), a major alkaloid of the piperideine chemotype in fire ant venoms, and its analogues, 2-methyl-6-tetradecyl-Δ1,6-piperideine (2) and 2-methyl-6-hexadecyl-Δ1,6-piperideine (3), was achieved by a facile synthetic method starting with glutaric acid (4) and urea (5). Compound 1 showed in vitro antifungal activity against Cryptococcus neoformans and Candida albicans with IC50 values of 6.6 and 12.4 μg/mL, respectively, and antibacterial activity against vancomycin-resistant Enterococcus faecium with an IC50 value of 19.4 μg/mL, while compounds 2 and 3 were less active against these pathogens. All three compounds strongly inhibited the parasites Leishmania donovani promastigotes and Trypanosoma brucei with IC50 values in the range of 5.0-6.7 and 2.7-4.0 μg/mL, respectively.
Asymmetric Homogeneous Hydrogenation of 2-Pyridones
Wysocki, Jedrzej,Schlepphorst, Christoph,Glorius, Frank
supporting information, p. 1557 - 1562 (2015/06/30)
An asymmetric homogeneous hydrogenation of 2(1H)-pyridones has been developed, using a ruthenium complex bearing two chiral N-heterocyclic carbene (NHC) ligands. To the best of our knowledge, the presented reaction is the first example of a homogeneous asymmetric conversion of 2-pyridones into the corresponding enantioenriched 2-piperidones.
ORTHO-SUBSTITUTED HALOALKYLSULFONANILIDE DERIVATIVE AND HERBICIDE
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Page/Page column 125, (2011/07/06)
Novel herbicides are provided. A haloalkylsulfonanilide derivative represented by the formula (1) or an agrochemically acceptable salt thereof: the formula (1): wherein A is -C(R7)(R8)- or -N(R9)-, W is an oxygen atom or a sulfur atom, n is an integer of from 1 to 4, R1 is halo C1 -C6 alkyl, R2 is a hydrogen atom, C1 - C6 alkyl or the like, each of R3 and R4 is independently a hydrogen atom, C1 - C6 alkyl or the like, each of R5, R6, R7 and R8 is independently a hydrogen atom, a halogen, C1 - C6 alkyl or the like, R9 is a hydrogen atom, C1 - C6 alkyl or the like, and X is halogen, C1 - C6 alkyl or the like.
Process for producing lactam
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Page 14, (2010/02/09)
A method for producing a lactam, which comprises subjecting an alicyclic primary amine to an oxidation reaction in the presence of a catalyst comprising a silicon oxide, to thereby obtain a lactam. A catalyst comprising a silicon oxide which is for use in the above-mentioned method.
