- Production of Piperidine and δ-Lactam Chemicals from Biomass-Derived Triacetic Acid Lactone
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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
- Chen, Bingfeng,Xie, Zhenbing,Peng, Fangfang,Li, Shaopeng,Yang, Junjuan,Wu, Tianbin,Fan, Honglei,Zhang, Zhaofu,Hou, Minqiang,Li, Shumu,Liu, Huizhen,Han, Buxing
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supporting information
p. 14405 - 14409
(2021/05/21)
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- Interrupted Pyridine Hydrogenation: Asymmetric Synthesis of δ-Lactams
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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.
- Wagener, Tobias,Lückemeier, Lukas,Daniliuc, Constantin G.,Glorius, Frank
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supporting information
p. 6425 - 6429
(2021/02/22)
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- Method for synthesizing lactam derivative without catalyst
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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%.
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Paragraph 0038-0041
(2019/07/10)
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- A Facile Direct Route to N-(Un)substituted Lactams by Cycloamination of Oxocarboxylic Acids without External Hydrogen
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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.
- Li, Hu,Wu, Hongguo,Zhang, Heng,Su, Yaqiong,Yang, Song,Hensen, Emiel J. M.
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p. 3778 - 3784
(2019/08/07)
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- Benzimidazole derivatives, preparation methods and uses theirof
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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.
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- An Efficient Two-Step Preparation of α-, β-, γ- or δ-Amino Acids from 2-Pyrazinones, 2-Hydroxypyrimidines or 2-Pyridones Respectively
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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.
- Zacharie, Boulos,Abbott, Shaun D.,Baigent, Christopher B.,Doyle, Christopher,Yalagala, Ravi Shekar
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p. 6486 - 6493
(2018/11/23)
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- Synthesis and Antimicrobial Evaluation of Fire Ant Venom Alkaloid Based 2-Methyl-6-alkyl-Δ1,6-piperideines
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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.
- Yan, Yujie,An, Yu,Wang, Xiaozhong,Chen, Yingqi,Jacob, Melissa R.,Tekwani, Babu L.,Dai, Liyan,Li, Xing-Cong
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p. 2795 - 2798
(2017/11/06)
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- Asymmetric Homogeneous Hydrogenation of 2-Pyridones
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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.
- Wysocki, Jedrzej,Schlepphorst, Christoph,Glorius, Frank
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supporting information
p. 1557 - 1562
(2015/06/30)
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- ORTHO-SUBSTITUTED HALOALKYLSULFONANILIDE DERIVATIVE AND HERBICIDE
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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.
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Page/Page column 125
(2011/07/06)
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- Process for producing lactam
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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.
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- Diels-Alder reactions of 6-substituted 1-(p-nitrobenzoyl)-5,6-dihydro-2-pyridinones
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The first examples of Diels-Alder cycloaddition reactions of 6-substituted 1-(p-nitrobenzoyl)-5,6-dihydro-2-pyridinones are described. This reaction benefits from the fact that the diene adopts an endo orientation trans to the axial substituent at C-6 due to A1,3 allylic type strain with the N-PNB protecting group.
- Dias,Fernandes,Zukerman-Schpector
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p. 100 - 104
(2007/10/03)
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- Two intermediates in the synthesis of decahydroisoquinolines with NMDA and AMPA receptor antagonist activity
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In 6-methyl-N-(4-nitrobenzoyl)-5,6-dihydropyridin-2(1H)-one, C13H12N2O4, (I), the piperidone ring is in a distorted half-chair conformation. In 8-methoxy-3-methyl-N-(4-nitrobenzoyl)-1,2,3,4,5,6,7,8 -octahydroisoquinoline-1,6-dione, C18H20N2O6, (II), the heterocyclic ring is in a slightly distorted half-boat conformation, while the other six-membered ring is in a distorted chair conformation. Compound (II) presents a strong intramolecular C - H···O hydrogen bond. In both (I) and (II), the molecules interact through C - H···O interactions.
- Zukerman-Schpector,Vega,Caracelli,Dias,Fernandes
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p. 1089 - 1091
(2007/10/03)
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- Stereoselective alkylation of N-Boc-2-pyrrolidinones and N-Boc-2- piperidinones. Synthesis and characterization of disubstituted lactams
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Alkylation of enolates of monosubstituted N-Boc lactams 4-6 afforded trans-disubstituted lactams as the major isomer. In the pyrrolidinone series, 1,3-induction seems to be ruled by steric interactions and the diastereoselection is low for the alkylation of enolates with small substituents at C-5 (e.g., Me) and methyl iodide. The trans selectivity improves with bulkier substituents at C-2 and/or bulkier electrophiles. The formation of 3,6-trans-disubstituted piperidinones benefits from the axial orientation of the substituent at C-2 due to the A strain with the N-Boc group and excellent trans preference is observed even in the alkylation of the lithium enolate of N-Boc-6-methyl piperidinone with methyl iodide.
- Maldaner, Adriano O.,Pilli, Ronaldo A.
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p. 13321 - 13332
(2007/10/03)
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- Asymmetric synthesis with chiral hydrogenolysable amines, ω-imino esters reduction: A diastereoselective route to ω-alkyl lactams
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Chiral methylbenzylamine is used to prepare ω-amino esters which are then transformed into ω-alkyl lactams with good diastereoselectivity.
- Marx,El Bouz,Celerier,Lhommet
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p. 4307 - 4310
(2007/10/02)
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- The stereochemistry of organometallic compounds XXXVI. Rhodium-catalysed reactions of unsaturated amines with hydrogen and carbon monoxide. A new synthesis of 2-piperidinones
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Rhodium-catalysed reactions of 5-aminopent-1-enes with carbon monoxide and hydrogen give 2-piperidinone derivatives in high yields under mild conditions.Reaction of allylamine under similar conditions gave exclusively 2-pyrrolidone in high yield and reactions of 4-aminobut-1-enes gave mixtures of 2-piperidinones and 2-pyrrolidinones.The role of the hydrogen in these reactions is discussed.
- Anastasiou, Despina,Jackson, W. Roy
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p. 399 - 410
(2007/10/02)
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- Stereoselective Synthesis and Stereochemical Determination of 2,5-Dialkylpyrrolidines and 2,6-Dialkylpiperidines
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ω-Alkyllactams 3 can be transformed into ω-alkyl cyclic β-enaminoesters 7 which are good precursors of insects venom alkaloids.A stereoselective synthesis of dialkylpyrrolidines and Solenopsine A is described followed by and easy stereochemical determination by 13C nmr.
- Bacos, D.,Celerier, J. P.,Marx, E.,Rosset, S.,Lhommet, G.
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p. 1387 - 1392
(2007/10/02)
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- STEREOSELECTIVE FORMAL SYNTHESIS OF (+/-)-MONOMORINE I FROM 6-METHYL-2-PIPERIDINONE
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The stereoselective formal synthesis of (+/-)-monomorine I from 6-methyl-2-piperidinone was achieved.A general method for the synthesis of ω-alkylated lactams is also described.
- Nagasaka, Tatsuo,Kato, Hiroki,Hayashi, Hideki,Shioda, Masako,Hikasa, Hiromi,Hamaguchi, Fumiko
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p. 561 - 566
(2007/10/02)
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- Process for the preparation of a lactam
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Disclosed is a process for preparing a lactam which consists essentially in the reductive amination in the gas phase of an oxoalkane carboxylic acid having the formula STR1 or an alkyl ester thereof, wherein R is an alkyl group having from 1 to 4 carbon atoms and n varies from 2 to 3, and wherein the reaction is carried out: A. in an atmosphere of hydrogen, and B. in the presence of a gas phase reactant selected from the group consisting of gaseous ammonia and a vaporized primary amine, and C. in the presence of a hydrogenation catalyst promoted with an alkali metal. The alkali metal particularly preferred as a promoter is sodium.
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- Anticonvulsive compositions and method of treating convulsive disorders
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An orally administered pharmaceutical formulation comprising a solid dosage form containing an aliphatic amino acid compound in which the carboxylic acid and primary amine are separated by three or four units. Administered in an acid pH range, the formulation is useful in the treatment of convulsive disorders and also has anxiolytic and sedative properties.
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- Anticonvulsive compositions and method of treating convulsive disorders
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A pharmaceutical formulation comprising aliphatic amino acid compounds in which the carboxylic acid and primary amine are separated by three or four units. The compositions are useful in the treatment of convulsive disorders and also have anxiolytic and sedative properties.
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- Vapor phase Beckmann rearrangement of the cyclohexanone oxime catalyzed by AlPO4-γAl2O3 systems
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Beckmann rearrangement of cyclohexanone oxime has been carried out in vapor phase by means of a pulse reactor unit directly coupled to a gas chromatograph.The catalysts chosen gave good yields of ε-caprolactam.Apparent rate constants and activation energies were calculated in terms of the kinetic model of Bassett and Habgood.Selectivity studies, using pulse experiments interpreted by OPE curves, led to the conclusion that ε-caprolactam and 5-cyanopent-1-ene were competitive products.A reaction pathway is proposed which is in agreement with both the observed rates and selectivities.
- Costa, A.,Deya, P.M.,Sinisterra, J.V.,Marinas, J.M.
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p. 1266 - 1270
(2007/10/02)
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