- Electrosynthesis of cyclopropane derivatives by a Perkin-type reaction
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Electrolysis of active methylene compounds at a Pt cathode in MeCN in the presence of vicinal dihaloalkanes leads to cyclopropane derivatives in yields up to 90percent.In the cases of CH-acids with low pKa it is expedient to apply more active dihaloalkanes, while for CH-acids with higher pKa the desired product yields may be raised using electrogenerated bases. - Key words: CH-acids; 1,2-dihaloalkanes; cyclopropanes; electrosynthesis; electroreduction; electronegative bases; azobenzene.
- Petrosyan, V. A.,Vasil'ev, A. A.,Tatarinova, V. I.
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Read Online
- Anionic ring-opening polymerization of alkyl 1- cyanocyclopropanecarboxylates
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Poly(alkyl 1-cyanotrimethylene-1-carboxylate)s (CH2CH 2C(CN)(COOR))n are the next higher chain homologues of poly(α-cyanoacrylate)s. They were synthesized via the anionic ring-opening polymerization of the corresponding alkyl 1-cyanocyclopropanecarboxylate monomers initiated with thiophenolate salts (PhSM, with M = Li, Na, K, and NBu4) and at temperatures above 50°C. Precipitation of the growing polymer chains at an early stage during the polymerization did not prevent further propagation, probably via polymerization in the solid or at the solid surface. The propagating cyanoacetate carbanion is very stable in a normal air atmosphere, surviving for long periods of time in the absence of strong acids. Although monodisperse polymers were obtained in most experiments (M w/Mn + and NBu 4+ counterions were used. Nonquantitative initiations characterized polymerizations initiated by PhSLi and PhSNa. Attempted polymerizations of ethyl 1-cyanocyclobutanecarboxylate failed under similar or slightly more energetic experimental conditions, with the thiophenolate initiator attacking the pendant ester rather than the cyclic methylene group.
- Kagumba, Lawino C.,Penelle, Jacques
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Read Online
- Synthesis, bioactivity, theoretical and molecular docking study of 1-cyano-N-substituted-cyclopropanecarboxamide as ketol-acid reductoisomerase inhibitor
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Ketol-acid reductoisomerase (KARI; EC 1.1.1.86) catalyzes the second common step in branched-chain amino acid biosynthesis. The catalyzed process consists of two stages, the first of which is an alkyl migration from one carbon atom to its neighbouring ato
- Liu, Xing-Hai,Chen, Pei-Quan,Wang, Bao-Lei,Li, Yong-Hong,Wang, Su-Hua,Li, Zheng-Ming
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- CATHODIC SYNTHESIS OF CYCLOPROPANE DERIVATIVES BY THE ELECTROLYSIS OF COMPOUNDS WITH AN ACTIVATED METHYLENE GROUP IN 1,2-DICHLOROETHANE
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The cathodic electrolysis of compounds with an activated methylene group in 1,2-dichloroethane leads to 1,1-disubstituted cyclopropanes.The current yield of these cyclopropane derivatives depends on the CH-acidity of the starting compounds and has a maximum at pKa ca.13.
- Vasil'ev, A. A.,Tatarinova, V. I.,Petrosyan, V. A.
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Read Online
- A new synthesis of bicyclic N,O- and N,S-enaminals by the anionic cyclization of alk-4-ynals with amino alcohols and amino thiols
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A reaction of alk-4-ynals with aliphatic amino alcohols or 2-aminoethanethiol in the system DMSO - KOH gives bicyclic N,O- and N,S-enaminals: 6-methylidenehexahydro-2H-pyrrolo[2,1-b][1,3]oxazines, 5-methylidenehexahydropyrrolo[2,1-b]oxazoles, or 5-methyl-
- Gvozdev,Shavrin,Nefedov
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Read Online
- MACROCYCLIC COMPOUNDS AS STING AGONISTS AND METHODS AND USES THEREOF
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Disclosed are macrocyclic compounds having the general Formula (I) or (II) and their tautomeric forms, stereoisomers, pharmaceutically acceptable salts, hydrates, solvates and prodrugs thereof, and their combination with suitable medicament, corresponding processes for the synthesis and pharmaceutical compositions and uses of compounds disclosed herein.
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Paragraph 0306-0307
(2021/01/29)
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- A class of chiral beta-hydroxyamide compounds, preparation method and applications thereof,
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The invention discloses a chiral beta-hydroxyamide compound and a preparation method thereof, wherein the compound is represented by a formula I. According to the invention, the raw material for preparing a non-natural chiral amino acid compound is obtained by carrying out catalytic hydrolysis on a prochiral diamide compound II with different substituents by using a Rhodococcus erythropolis AJ270microbial system, wherein the use amount of the Rhodococcus erythropolis can be adjusted according to the use amount of a substrate, the reaction solvent is a common buffer solution with the pH valueof 6.0-8.0, the temperature is 20-37 DEG C, the reaction time is 3-120 h, and the Rhodococcus erythropolis microbial catalytic system can be cultured through fermentation and conveniently stored; andwith the application of the biotransformation to prepare chiral monoamide carboxylic acid and dicarboxylic acid, the characteristics of simplicity and convenience in operation, high reaction efficiency, mild reaction conditions, high enantioselectivity, easiness in product separation and high product purity are achieved, and the application prospect is god.
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Paragraph 0167; 0178
(2020/03/12)
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- Quinazolinone Compound and Application Thereof
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The present invention relates to a series of quinazolinone compounds and applications thereof as PI3Kα inhibitors. In particular, the present invention relates to a compound shown in formula (I) and a tautomer or pharmaceutically acceptable salt thereof.
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Paragraph 0760-0762
(2020/11/27)
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- PARTIALLY SATURATED NITROGEN-CONTAINING HETEROCYCLIC COMPOUND
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There are provided compounds having a superior PHD2 inhibitory effect that are represented by general formula (I'): (in the above-mentioned general formula (I'), W, Y, R2, R3, R4, and Y4 are as described hereinabove), or pharmaceutically acceptable salts thereof.
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Paragraph 0289; 0290
(2015/06/17)
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- NOVEL COMPOUNDS
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Disclosed are novel retinoid-related orphan receptor gamma (RORγ) modulators and their use in the treatment of diseases mediated by RORγ.
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Page/Page column 66
(2015/12/17)
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- Benzamides
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The present invention is directed to benzamide containing compounds which inhibit the P2X7 receptor
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Paragraph 0100
(2014/05/07)
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- LYSOPHOSPHATIDIC ACID RECEPTOR ANTAGONISTS
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Compounds, methods of making such compounds, pharmaceutical compositions and medicaments comprising such compounds, and methods of using such compounds to treat, prevent or diagnose diseases, disorders, or conditions associated with one or more of the lysophosphatidic acid receptors are provided.
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Paragraph 0793
(2013/03/26)
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- Synthesis, crystal structure and biological activity of 1-Cyano-N-(4-bromophenyl)cyclopropanecarboxamide
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A cyclopropane derivative, 1-cyano-N-(4-bromophenyl)cyclopropanecarboxamide (C11H9N2OBr) was synthesized and its structure was studied by X-ray diffraction, FTIR, 1H NMR spectrum and MS. The crystal is triclinic, space group P-1 with α = 8.902(4), β = 10.
- Xue, Yong-Lai,Zhang, Yong-Gang,Liu, Xing-Hai
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experimental part
p. 3016 - 3018
(2012/08/29)
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- Synthesis, crystal structure and biological activity of 1-cyano-N-phenylcyclopropanecarboxamide
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A cyclopropane derivative, 1-cyano-N-phenylcyclopropanecarboxamide (C 11H10N2O) was synthesized and its structure was studied by X-ray diffraction, FTIR, 1H NMR spectrum and MS. The crystals are monoclinic, space group Pbc
- Xue, Yong-Lai,Liu, Xing-Hai,Zhang, Yong-Gang
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experimental part
p. 1571 - 1574
(2012/09/07)
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- Synthesis, crystal structure and biological activity of 1-Cyano-N-(2,4-dichlorophenyl)cyclopropanecarboxamide
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A cyclopropane derivative, 1-cyano-N-(2,4-dichlorophenyl) cyclopropanecarboxamide (C11H8N2OCl2) was synthesized and its structure was studied by X-ray diffraction, FTIR, 1H NMR, MS and elemental analysis. The crystals are monoclinic, space group C2 with a
- Xue, Yong-Lai,Zhang, Yong-Gang,Liu, Xing-Hai
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experimental part
p. 5087 - 5089
(2012/10/08)
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- BICYCLIC ARYL SPHINGOSINE 1-PHOSPHATE ANALOGS
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Compounds that have agonist activity at one or more of the SlP receptors are provided. The compounds are sphingosine analogs that, after phosphorylation, can behave as agonists at SlP receptors.
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Page/Page column 64
(2011/02/24)
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- Synthesis of a novel analogue of DPP-4 inhibitor Alogliptin: Introduction of a spirocyclic moiety on the piperidine ring
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We report the synthesis of a novel analogue of Alogliptin via condensation of two key intermediates one of which is an aminopiperidine derivative bearing a spirocyclic ring on the piperidine moiety. Preparation of the aminopiperidine intermediate was carried out by constructing the cyclopropyl ring prior to assembling the piperidine ring.
- Kodimuthali, Arumugam,Pal, Manojit,Prasunamba, Padala Lakshmi
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supporting information; experimental part
(2010/11/21)
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- AMIDE SUBSTITUTED IMIDAZOPYRIDINES, IMIDAZOQUINOLINES, AND IMIDAZONAPHTHYRIDINES
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Imidazopyridine, imidazoquinoline, and imidazonaphthyridine compounds having an amide substituent at the 1-position, pharmaceutical compositions containing the compounds, intermediates, and methods of making and methods of use of these compounds as immunomodulators, for modulating cytokine biosynthesis in animals and in the treatment of diseases including viral and neoplastic diseases are disclosed.
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Page/Page column 73
(2010/11/28)
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- SUBSTITUTED IMIDAZOQUINOLINES, IMIDAZOPYRIDINES, AND IMIDAZONAPHTHYRIDINES
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Imidazo-quinoline, -pyridine, and -naphthyridine ring systems (particularly quinolines, tetrahydroquinolines, pyridines, [1,5]naphthyridines, [1,5]tetrahydronaphthyridines) substituted at the 1-position with a cyclic substituent, pharmaceutical compositions containing the compounds, methods of making these compounds, and methods of use of these compounds as immunomodulators, for inducing cytokine biosynthesis in animals and in the treatment of diseases including viral and neoplastic diseases are disclosed.
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Page/Page column 162
(2010/10/20)
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- Imidazolium salts as phase transfer catalysts for the dialkylation and cycloalkylation of active methylene compounds
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The efficient synthesis of 1,1-disubstituted derivatives and the construction of cyclopropane and cyclopentane ring systems via dialkylation and cycloalkylation reactions of active methylene compounds using imidazolium salts as phase transfer catalyst is described. The dialkylation and cycloalkylation reactions of active methylene compounds in the presence of readily available imidazolium salts (ionic liquids) as phase transfer catalysts were performed to afford the respective dialkylated or cycloalkylated products. This method is very efficient for the synthesis of 1,1-disubstituted derivatives and cyclopropane and cyclopentane ring systems in a facile manner.
- Muthusamy, Sengodagounder,Gnanaprakasam, Boopathy
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p. 635 - 638
(2007/10/03)
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- Microwave assisted phase transfer catalysis: An efficient solvent free method for the synthesis of cyclopropane derivatives
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Microwave assisted solvent free synthesis of cyclopropane derivatives 2a-e starting from active methylene compounds 1a-e and 1,2-dibromoethane under phase transfer conditions is described.
- Gumaste,Khan, Asgar J.,Bhawal,Deshmukh
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p. 420 - 422
(2007/10/03)
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- Practical large scale preparation of activated cyclopropanes
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Simple and practical experimental conditions for the large scale preparation of activated cyclopropanes by K2CO3 promoted cycloalkylation of malonate precursors with 1,2-dibromoethane are described.
- Lavoisier, Tania,Rodriguez, Jean
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p. 525 - 530
(2007/10/03)
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- Latent inhibitors part 11. The synthesis of 5-spirocyclopropyl dihydroorotic acid
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Approaches to the synthesis of 5-spirocyclopropyldihydroorotic acid are described. Difficulties were encountered in the lack of reactivity of diethyl 2-oxobutandicarboxylate and its derivatives towards cyclopropanation. Potential intermediates were prepar
- Husbands, Stephen,Fraser, William,Suckling, Colin J.,Wood, Hamish C. S.
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p. 865 - 870
(2007/10/02)
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- Preparation and Cleavage of Some Cyclopropane Derivatives
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Alkylation of active methylene compounds with 1,2-dibromoethane using anhyd.K2CO3/DMF at room temperature gives cyclopropane derivatives which undergo selective transformation by simple methods.Cyclopropanes, obtained by the condensation of α-diazoacetophenones with olefins, are cleaved to trisubstituted olefins with Grignard reagent.Hydration of the products has also been studied.
- Podder, Ranjan Kumar,Sarkar, Ranjit Kumar,Ray, Suvas C.
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p. 530 - 536
(2007/10/02)
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- A Facile Synthesis of Dialkyl Cyclopropane-1,1-dicarboxylates and Alkyl 1-Cyanocyclopropanecarboxylates by Phase-Transfer Alkylation
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The efficient syntheses of dialkyl cyclopropane-1,1-dicarboxylates and alkyl 1-cyanocyclopropanecarboxylates by alkylation of dialkyl malonates and alkyl cyanoacetates with 1,2-dihaloethanes are described.The importance of a certain amount of water under the solid-liquid phase-transfer conditions is demonstrated in the reactions.
- Heiszman, Jozsef,Bitter, Istvan,Harsanyi, Kalman,Toeke,, Laszlo
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p. 738 - 739
(2007/10/02)
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- Stereochemical studies on the reactions catalyzed by the PLP-dependent enzyme 1-aminocyclopropane-1-carboxylate deaminase
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The stereochemical course of 1-aminocyclopropane-1-carboxylate deaminase which catalyzes the fragmentation of the cyclopropane substrate to alpha -ketobutyrate and ammonia has been unraveled with the help of substrates stereospecifically labeled with deuterium and/or tritium, and this has afforded important information about the process occurring at the active site during enzymatic conversion.
- Liu,Auchus,Walsh
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p. 5335 - 5348
(2007/10/07)
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- CYCLOALKYLATION BY THE α,ω-DIBROMIDES OF COMPOUNDS CONTAINING AN ACTIVATED METHYLENE GROUP AS A METHOD FOR THE SYNTHESIS OF 1,1-DISUBSTITUTED CYCLOALKENES
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A convenient preparative method was developed for the cycloalkylation of active methylene compounds, including β-diketones, by the dibromides BrCH2(CH2)nCH2Br (n = 0,1,2) in the presence of an excess of potassium carbonate in DMSO.The reaction gives high yields for the dibromides with n = 0 and 2, whereas the formation of cyclobutanes (n=1) is complicated by O,C-alkylation.The 1-substituted 1-acylcyclopropanes undergo thermal isomerization to the corresponding dihydrofuranes.
- Zefirov, N. S.,Kuznetsova, T. S.,Kozhushkov, S. I.,Surmina, L. S.,Rashchupkina, Z. A.
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p. 474 - 480
(2007/10/02)
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