- Ring-Expansion Reactions Catalyzed by Hydrophobic Vitamin B12 in Synthetic Bilayer Membrane
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Heptapropyl cobyrinate perchlorate catalyzed the ring-expansion reactions, which convert 2-methyl-1,3-cyclopentanedion and 3-methyl-2-pyrrolidinone into 1,4-cyclohexanedione and 2-piperidinone, respectively, in single-compartment bilayer vesicles.
- Murakami, Yukito,Hisaeda, Yoshio,Ohno, Teruhisa,Matsuda, Yoshihisa
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Read Online
- Efficient palladium catalysis for the upgrading of itaconic and levulinic acid to 2-pyrrolidones followed by their vinylation into value-added monomers
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The production of monomers from bio-based platform chemicals shows great potential to reduce the chemical industry's demand for fossil resources. We herein present a two-step approach, which yields N-vinyl-2-pyrrolidone monomers from bio-based carboxylic acids, such as itaconic and levulinic acid. A highly active, heterogeneous palladium catalyst facilitating the reductive amidation of itaconic acid (TOF = 950 molPyr·molPd-surface-1 h-1) as well as the reductive amination of levulinic acid (TOF = 4000 molPyr·molPd-surface-1 h-1) was designed. Especially the reductive amidation of itaconic acid to 3- and 4-methyl-2-pyrrolidone was found to be structure sensitive. A clear trend between Pd particle size and catalyst activity could be shown by the synthesis of Pd/C catalysts with varying Pd particle sizes. The vinylation of the synthesized methyl-2-pyrrolidones with acetylene was tested using common industrial conditions (10-18 bar acetylene, 150 °C, KOH catalyst, no solvent). Similar to the industrial vinylation of 2-pyrrolidone, good yields of up to 80% N-vinyl-methyl-2-pyrrolidone were received. Therefore, and due to the excellent maximum yield of methyl-2-pyrrolidones in reductive amidation (95 mol%), the envisioned process can be a promising drop-in technology, directly replacing fossil resources in the production of an established monomer class. This journal is
- Haus, Moritz O.,Hofmann, Jan P.,Konrad, Marc,Louven, Yannik,Palkovits, Regina
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p. 4532 - 4540
(2020/11/02)
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- N-(AZAARYL)CYCLOLACTAM-1-CARBOXAMIDE DERIVATIVE, PREPARATION METHOD THEREFOR, AND USE THEREOF
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An N-(azaaryl)cyclolactam-1-carboxamide derivative having a structure of formula (I), a preparation method therefor, and a use thereof are disclosed in the application. Each substituent are defined in the specification and claims. The series of compounds of the application can be widely applied in the preparation of drugs for treating cancer, tumor, autoimmune disease, metabolic disease or metastatic disease, particularly for treating ovarian cancer, pancreatic cancer, prostate cancer, breast cancer, cervical cancer, glioblastoma, multiple myeloma, metabolic disease, neurodegenerative disease, primary tumor site metastasis or osseous metastasis cancer, and are expected to be developed into a new generation of CSF-1R inhibitor drugs.
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Paragraph 0143; 0289; 0290
(2020/03/23)
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- Extending the chemical product tree: A novel value chain for the production of: N -vinyl-2-pyrrolidones from biogenic acids
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The sustainable production of polymers from biogenic platform chemicals shows great promise to reduce the chemical industry's dependence on fossil resources. In this context, we propose a new two-step process leading from dicarboxylic acids, such as succinic and itaconic acid, to N-vinyl-2-pyrrolidone monomers. Firstly, the biogenic acid is reacted with ethanolamine and hydrogen using small amounts of water as solvent together with solid catalysts. For effective conversion, the optimal catalyst (carbon supported ruthenium) has to hold the ability of activating H2 as well as (imide) CO bonds. The obtained products, N-(2-hydroxyethyl)-2-pyrrolidones, are subsequently converted in a continuous gas phase dehydration over simple sodium-doped silica, with excellent selectivity of above 96 mol% and water as the sole by-product. With a final product yield of ≥72 mol% over two process steps and very little waste due to the use of heterogeneous catalysis, the proposed route appears promising-commercially as well as in terms of Green Chemistry.
- Haus, Moritz Otto,Louven, Yannik,Palkovits, Regina
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supporting information
p. 6268 - 6276
(2019/12/03)
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- Carbazole-containing amides and ureas: Discovery of cryptochrome modulators as antihyperglycemic agents
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A series of novel carbazole-containing amides and ureas were synthesized. A structure–activity relationship study of these compounds led to the identification of potent cryptochrome modulators. Based on the desired pharmacokinetic/pharmacodynamic parameters and the results of efficacy studies in db/db mice, compound 50 was selected for further profiling.
- Humphries, Paul S.,Bersot, Ross,Kincaid, John,Mabery, Eric,McCluskie, Kerryn,Park, Timothy,Renner, Travis,Riegler, Erin,Steinfeld, Tod,Turtle, Eric D.,Wei, Zhi-Liang,Willis, Erik
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supporting information
p. 293 - 297
(2018/01/04)
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- CARBAZOLE-CONTAINING AMIDES, CARBAMATES, AND UREAS AS CRYPTOCHROME MODULATORS
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The subject matter herein is directed to carbazole-containing amide, carbamate, and urea derivatives and pharmaceutically acceptable salts or hydrates thereof of structural formula I wherein the variable R1, R2, R3, R4, R5, R6, R7, A, D, E, G, J, L, M, Q, a, and b are accordingly described. Also provided are pharmaceutical compositions containing the compounds of formula I to treat a Cry-mediated disease or disorder, such as diabetes, complications associated with diabetes, Cushing's syndrome, NASH, NAFLD, asthma, and COPD.
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Paragraph 0299
(2015/10/28)
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- MIXTURES OF ITACONIC ACID OR ITACONIC ACID DERIVATIVES AND PRIMARY AMINES FOR PRODUCING 1,3- AND 1,4-ALKYL METHYL PYRROLIDONES
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The present invention relates to a mixture comprising itaconic acid or an itaconic acid derivative and a primary amine of the formula (I) [in-line-formulae]R—NH2??(I)[/in-line-formulae] where the molar ratio of primary amine to itaconic acid or the itaconic acid derivative is in the range from 0.5:1 to 20:1, wherein the mixture comprises 50 mole percent or less of 4-carboxypyrrolidones of the formula (II), derivatives of the 4-carboxypyrrolidones of the formula (II) and 4-carbamidopyrrolidones of the formula (III) based on the itaconic acid used or the itaconic acid derivative used and in which R is a linear or branched saturated aliphatic radical having 1 to 24 carbon atoms or a saturated cycloaliphatic radical having 3 to 24 carbon atoms. The invention further provides for the use of the inventive mixtures for preparing 1,3-alkylmethylpyrrolidones and/or 1,4-alkylmethylpyrrolidones, and also a process for preparing 1,3-alkylmethylpyrrolidones and/or 1,4-alkylmethylpyrrolidones. In addition, the present invention relates to mixtures comprising 1,3-alkylmethylpyrrolidones and/or 1,4-alkylmethylpyrrolidones and 1,3-alkylmethylpyrrolidines, where the proportion of 1,3-alkylmethylpyrrolidines is in the range from 10 to 10 000 ppm, and to mixtures comprising 1,3-alkylmethylpyrrolidone and 1,4-alkylmethylpyrrolidone, wherein the molar ratio of 1,3-alkylmethylpyrrolidone to 1,4-alkylmethylpyrrolidone is in the range from 1:1 to 10:1.
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Page/Page column 12
(2011/10/19)
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- COMPOUNDS FOR TREATING DISORDERS MEDIATED BY METABOTROPIC GLUTAMATE RECEPTOR 5, AND METHODS OF USE THEREOF
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Provided herein are compounds and methods of synthesis thereof. The compounds set forth herein are useful for the treatment, prevention, and/or management of various disorders, such as neurological disorders, neurodegenerative disorders, neuropsychiatric disorders, disorders of cognition, learning or memory, gastrointestinal disorders, lower urinary tract disorder, and cancer. Compounds set forth herein modulate the activity of metabotropic glutamate receptor 5 (mGluR5) in the central nervous system or the periphery. Pharmaceutical formulations containing the compounds and their methods of use are also provided herein.
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Page/Page column 140-141
(2011/07/07)
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- PROCESS FOR STRAIGHTENING KERATIN FIBRES WITH A HEATING MEANS AND DENATURING AGENTS
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The invention relates to a process for straightening keratin fibres, comprising: (i) a step in which a straightening composition containing at least two denaturing agents is applied to the keratin fibres, (ii) a step in which the temperature of the keratin fibres is raised, using a heating means, to a temperature of between 110 and 250° C.
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- Evaluation of pyrrolidin-2-imines and 1,3-thiazolidin-2-imines as inhibitors of nitric oxide synthase
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Syntheses and evaluation of pyrrolidin-2-imines and 1,3-thiazolidin-2- imines as inhibitors of nitric oxide synthase (NOS) are discussed. An extensive SAR was established for pyrrolidin-2-imines class of compounds. The amidines came out as the most potent inhibitors in addition to displaying selectivity.
- Shankaran,Donnelly, Karla L.,Shah, Shrenik K.,Guthikonda, Ravindra N.,MacCoss, Malcolm,Humes, John L.,Pacholok, Stephen G.,Grant, Stephan K.,Kelly,Wong
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p. 4539 - 4544
(2007/10/03)
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- Optically active biphenyl derivative and process for optical resolution
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A biphenyl compound having the formula (I) is newly separated into its optical active compound and useful as an optically separating agent: STR1 wherein W, X and Y are each an atom or atomic group selected from among H, F, Cl, Br, I, CH3, CF3, OH, OCH3, NH2 and N(CH3)2 and Z is an atom or atomic group selected from among Cl, Br, I, CH3 and OCH3, R is an atomic group having 1 to 20 carbon atoms and containing a polar functional group selected from among STR2
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- Cobalt-Catalyzed Photochemical Carbonylation of Allylic Amines
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Allylic amines are carbonylated at room temperature in the presence of cobalt catalysts under UV irradiation.With allylamine, 2-pyrrolidone, N,N'-diallylurea, and N-allyl-3-butenamide were obtained.The photochemical cleavage of C-N bond of amines coordinated to cobalt metals was suggested.
- Mori, Sadayuki,Matsuyoshi, Hiroaki,Kudo, Kiyoshi,Sugita, Nobuyuki
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p. 1397 - 1400
(2007/10/02)
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- Optically Active 4,4',6,6'-Tetrachloro-2,2'-bis(hydroxydiphenylmethyl)biphenyl As a Host for Optical Resolution and Chiral Shift Reagent
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The title biphenyl derivative was found to be useful as a host for optical resolution and as a chiral shift reagent for the determination of the optical purity and the absolute configuration of a wide variety of chiral compounds.
- Toda, Fumio,Toyotaka, Ritsuji,Fukuda, Hideji
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p. 303 - 306
(2007/10/02)
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- Ti(O-i-Pr)4 MEDIATED LACTAMIZATIONS
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Ti(O-i-Pr)4 promotes the formation of 5- and 6-membered lactams from primary and secondary ω-amino acids, giving the lactams in good yield (75-93percent).
- Mader, Mary,Helquist, Paul
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p. 3049 - 3052
(2007/10/02)
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- The Stereochemistry of Organometallic Compounds. XXXII. Hydrocyanation of Derivatives of Amino Alkynes
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The hydrocyanation of a range of amino alkyne derivatives has been studied by using nickel-based catalyst systems.The phthalimido derivatives have been shown to give good yields of unsaturated cyano amine derivatives, and some of these have been converted into both saturated and unsaturated amino acids.
- Jackson, W. Roy,Perlmutter, Patrick,Smallridge, Andrew J.
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p. 1201 - 1208
(2007/10/02)
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- A MILD AND FACILE ROUTE TO ω-AMINO ESTERS
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Lactim ethers are conveniently prepared from the corresponding lactam.The salt prepared by protonation with HCl or HBF4 is hydrolyzed in neutral water at ambient temperatures to give good yields of the ω-amino ester.
- Menezes, Royce,Smith, Michael B.
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p. 1625 - 1636
(2007/10/02)
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- SYNTHESIS AND REACTIVITY OF METHYL γ-AZIDO BUTYRATES AND ETHYL δ-AZIDO VALERATES AND OF THE CORRESPONDING ACID CHLORIDES AS USEFUL REAGENTS FOR THE AMINOALKYLATION
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The azidoesters 13 and 14 and the corresponding acid chlorides 22 and 23 are shown to be interesting reagents for the nucleophilic and electrophilic aminoalkylation. α-substituted methyl γ-azidobutyrates 13 and ethyl δ-azido valerates 14 are easily accessible by alkylation of the lithium enolates of the parent compounds 13a and 14a respectively.Their chemoselective reduction leads to 3-substituted lactams 18 and 19.The acid chlorides 22 and 23 issued from 13 and 14 react with nucleophilic reagents, i.e. the carbanion of Meldrum acid, trimethylphosphite and n-butylmanganous iodide giving the the ω-azido,β-ketoesters 25 and 26, the ω-azido,α-acylphosphonates 29 and 30 and the ω-azido ketones 38 and 39 respectively in good yields.The treatment of 25 and 26 by Ph3P in anhydrous ether leads to the cyclic β-enaminoesters 27 and 28 whereas the α-acylphosphonates give the cyclic iminophosphonates 33 and 34a in good yields.These cyclizations occur via an intramolecular aza-Wittig reaction.
- Khoukhi, N.,Vaultier, M.,Carrie, R.
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p. 1811 - 1822
(2007/10/02)
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- New Reactions of Deoxyvasicinone. Part 4.
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Analogues of deoxyvasicinone (1) in which the pyrrolo ring is substituted, enlarged, or attached to the a face of the quinazolone system were prepared and several reactions of these analogues with electrophilic reagents have been investigated.
- Dunn, A. D.,Kinnear, K. I.
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- Ammonialytic cleavage of lactams to ω-aminonitriles
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Ammonialytic cleavage of lactams to ω-aminonitriles is effectively promoted by the use of catalysts selected from among molecular sieves and alkaine earth silicates. Molecular sieves additionally reduce the formation of undesired polymer.
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