- Synthesis method of phenylacetaldehyde derivative
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The present invention discloses a synthesis method of phenylacetaldehyde derivative, a benzaldehyde derivative is adopted as a raw material, an intermediate 2-methoxyvinylphenyl derivative is obtained through synthesis, then the phenylacetaldehyde derivative is obtained through synthesis, and the substituent group R of the benzaldehyde derivative includes but is not limited to m-methyl, m-ethyl, m-nitrile group, p-methyl, o-methyl, o-nitro and 2, 6-dimethyl. The synthesis process is simple, synthesis conditions are mild, post-treatment is relatively simple, and industrial production is easy; the universality is good, and substrates with different functional groups are compatible; the yield is considerable, part of compounds are almost quantitatively converted, and the requirement of atom economy is met.
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Paragraph 0041; 0046-0047; 0050
(2021/08/07)
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- Exploring the Potential of 2-(2-Nitrophenyl)ethyl-Caged N-Hydroxysulfonamides for the Photoactivated Release of Nitroxyl (HNO)
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The emergence of nitroxyl (HNO) as a biological signaling molecule is attracting increasing attention. HNO-based prodrugs show considerable potential in treating congestive heart failure, with HNO reacting rapidly with metal centers and protein-bound and free thiols. A new class of 2-(2-nitrophenyl)ethyl (2-NPE)-photocaged N-hydroxysulfonamides has been developed, and the mechanisms of photodecomposition have been investigated. Three photodecomposition pathways are observed: The desired concomitant C-O/N-S bond cleavage to generate HNO, sulfinate, and 2-nitrostyrene, C-O bond cleavage to give the parent sulfohydroxamic acid and 2-nitrostyrene, and O-N bond cleavage to release a sulfonamide and 2-nitrophenylacetaldehyde. Laser flash photolysis experiments provide support for a Norrish type II mechanism involving 1,5-hydrogen atom abstraction to generate an aci-nitro species. A mechanism is proposed in which the (Z)-aci-nitro intermediate undergoes either C-O bond cleavage to release RSO2NHO(H), concerted C-O/N-S bond cleavage to generate sulfinate and HNO, or isomerization to the (E)-isomer prior to O-N bond cleavage. The pKa of the N(H) of the N-hydroxysulfonamide plays a key role in determining whether C-O or concerted C-O/N-S bond cleavage occurs. Deprotonating this site favors the desired C-O/N-S bond cleavage at the expense of an increased level of undesired O-N bond cleavage. Triplet state quenchers have no effect on the observed photoproducts.
- Bharadwaj, Vinay,Brasch, Nicola E.,Rahman, Mohammad S.,Sampson, Paul,Seed, Alexander J.
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p. 16448 - 16463
(2021/12/06)
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- 4H-PYRROLO[3,2-C]PYRIDIN-4-ONE DERIVATIVES
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Compounds of formula (I) for use in the treatment or prophylaxis of a disease, which is a hyperproliferative disease and/or a disorder responsive to induction of cell death, selected from a haematological tumour, a solid tumour and/or metastases thereof, said tumour harbouring a mutant EGFR with exon 19 or 21 mutations, and their use as pharmaceuticals.
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Page/Page column 93-94
(2020/11/03)
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- 4H-PYRROLO[3,2-C]PYRIDIN-4-ONE DERIVATIVES
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Compounds of formula (I) processes for their production and their use as pharmaceuticals.
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Page/Page column 85
(2019/05/15)
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- Synthetic process of aromatic acetaldehyde compound
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The invention provides a synthetic process of an aromatic acetaldehyde compound; the synthetic method includes forming a mixed solution via starting material A with N,N-dimethylformamide dimethyl acetal; continuously feeding the mixed solution into a continuous reactor to carry out enamination reaction to obtain enamide B, and discharging the enamide B from the continuous reactor during enamination reaction; preparing aromatic acetaldehyde compound C with the enamide B, wherein the starting material A has a structural formula shown as formula (1), the enamide B has a structural formula shown as formula (2), and the aromatic acetaldehyde compound C has a structural formula shown as formula (3). By continuously feeding the mixed solution of reaction materials into the reactor to carry out enamination reaction, enamination reaction is continuously performed; continuous production of aromatic acetaldehyde compounds is achieved, reaction time is shortened, and reaction efficiency is improved.
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Paragraph 0063; 0067; 0068
(2017/11/30)
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- Synthesis of indolines via a SmI2 promoted domino nitro reduction-intramolecular aza-Michael reaction
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A simple and straightforward synthesis of substituted indolines based on a domino nitro reduction intramolecular aza-Michael reaction is described. The reaction employs Samarium diiodide under mild conditions for the addition of dibromoacetic acid to substituted 2-(2-nitrophenyl) acetaldehyde derivatives and their subsequent cyclization upon nitro group reduction to provide corresponding indoline heterocycles in good yields. This "one pot" strategy also permitted the expeditious synthesis of a 1,2,3,4-tetrahydroquinoline, whereas the seven-membered 2,3,4,5-tetrahydrobenzoazepines compounds were not formed under these reaction conditions.
- Ramos, Josierika A. Ferreira,Araújo, Carolina S.,Nagem, Tanus J.,Taylor, Jason G.
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- Facile synthesis of indolines by a tandem nitro-reduction Aza Michael addition reaction
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A diverse array of substrates are conveniently prepared by coupling diazonium salts to ethyl vinyl ether and subjecting the resultant aldehyde intermediate to a Wittig reaction to provide α,β-unsaturated esters with only one purification step. The cyclisation of 4-aryl-but-2-enoates is carried out in the presence of stoichiometric amounts of SnCl 22H2O and thus this one-pot strategy also permitted the expeditious synthesis of indolines in good yield. The Japan Institute of Heterocyclic Chemistry.
- Ventura, Wellington Martins,Souza De Assis, Luiz Guilherme,Taylor, Jason Guy
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p. 2023 - 2029
(2013/10/22)
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- Continuous-flow synthesis of monoarylated acetaldehydes using aryldiazonium salts
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Anilines and ethyl vinyl ether can be used as precursors for a process that is the synthetic equivalent of the α-arylation of acetaldehyde enolate. The reaction manifests a high level of functional group compatibility, allowing the ready preparation of a number of synthetically valuable compounds.
- Chernyak, Natalia,Buchwald, Stephen L.
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supporting information; experimental part
p. 12466 - 12469
(2012/09/05)
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- An unusual route to a quinoline 1-oxide via intramolecular addition of an enolate to an aromatic nitro group
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A mixture of ethyl 4-(2-nitrophenyl)butenoates undergoes an unusual intramolecular cyclisation in the presence of a catalytic amount of potassium tert-butoxide. 2011 · Copyright by Walter de Gruyter.
- Moreira, Nayara Da Rocha F.,De Oliveira, Tania T.,Nagem, Tanus J.,Taylor, Jason G.
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scheme or table
p. 203 - 205
(2012/03/12)
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- WNT PATHWAY ANTAGONISTS
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The present invention relates to known and novel compounds of formula (I) as herein described and pharmaceutical compositions thereof. The compounds of formula (I) have inhibitory effect on the Wnt pathway and are therefore useful in the preparation of a medicament, in particular for the treatment of cancer.
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Page/Page column 79
(2011/04/26)
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- Facile, environmentally friendly synthesis of benzaldehyde and phenylacetaldehyde analogs from readily available toluene derivatives
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A facile environmentally friendly synthesis of bezaldehyde and phenylacetaldehyde analogs from readily available toluene derivatives is described. Oxidation of the styrylamines by H2O2 H2O2 affords benzaldehydes in moderate yields, while the hydrolysis of styrylamines afforded phenylacetaldehyde analogs in good yields. Copyright
- Dai, Liyan,Yu, Jie,Chen, Yingqi,Yu, Shichao
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p. 3078 - 3084
(2011/09/14)
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- THIAZOL-GUANIDINE DERIVATIVES USEFUL AS A (BETA)- RELATED PATHOLOGIES
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This invention relates to novel compounds having the structural formula I below: and to their pharmaceutically acceptable salt, compositions and methods of use. These novel compounds provide a treatment or prophylaxis of cognitive impairment, Alzheimer Di
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Page/Page column 68
(2008/06/13)
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- PHENYLCARBOXYLIC ACID DERIVATIVES AND USE THEREOF FOR THE TREATMENT OF DIABETES
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The invention relates to compounds of general formula (1): in which R1, R2, R3, R4, R5, A, B, D and E are as defined in Claim 1, and also to the preparation process therefor and the therapeutic use thereof. These compounds can be used in the treatment of pathologies associated with hyperglycaemia.
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Page/Page column 65
(2010/02/15)
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- Nitric acid in dichloromethane solution. Facile preparation from potassium nitrate and sulfuric acid
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Pure dry HNO3 can be liberated from KNO3 with 96% H2SO4 directly into CH2Cl2 to yield solutions of variable concentration for use in a number of organic reactions. The present method efficiently replaces the employment of 100% HNO3 in some synthetic applications, avoiding the problems associated in storage and handling the acid.
- Strazzolini, Paolo,Giumanini, Angelo G.,Runcio, Antonio
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p. 1387 - 1389
(2007/10/03)
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- Experiments on the Chaperon effect in the nitration of aromatics
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A nitro group may be effectively delivered to the ortho position of alkylbenzenes, provided that a suitable chaperon function is located in α- position and a dilute of HNO3 in CH2Cl2 is used. The carbonyl function of an aldehyde or ketone is the best choice, but a carboxyl, alkoxycarbonyl, and amide groups all work well. The ether function showed a less pronounced ortho orientation effect, whereas the hydroxyl group was too prone to oxidation. Side reactions were minimal under the conditions employed. A para chaperon effect was seemingly at work in the CH2Cl2 nitration of benzenepropanenitrile. All the results were compared with the corresponding classical nitration in H2SO4.
- Strazzolini, Paolo,Giumanini, Angelo G.,Runcio, Antonio,Scuccato, Massimo
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p. 952 - 958
(2007/10/03)
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- 2-(2-aminophenyl)-acetaldehyde dimethyl acetal: A novel reagent for the protection of carboxylic acids
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The synthesis and use of 2-(2-aminophenyl)-acetaldehyde dimethyl acetal 1 are described. The amides 2, derived from this amine and carboxylic acids, are stable under basic conditions and thus can be regarded as the protected carboxylic acids. The corresponding carboxylic acids are regenerated by conversion of 2 into indolylamides 3 by treatment with CSA and subsequent hydrolysis with LiOOH or NaOH. In addition, 3 can be easily converted to esters, amides, and aldehydes.
- Arai, Eri,Tokuyama, Hidetoshi,Linsell, Martin S.,Fukuyama, Tohru
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- New models for the study of the racemization mechanism of carbodiimides. Synthesis and structure (X-ray crystallography and 1H NMR) of cyclic carbodiimides
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The crystal and molecular structure of carbodiimides 2 (5,6,18,19-tetradehydro-5,12,13,18,25,26-hexahydrotetrabenzo[d,h,m,q][1,3,10,12] tetraazacyclooctadecine) and 3 (8,10,22,24-tetraazapentacyclo-[23.3.1.3,7.111,15.1 17,21]dotriaconta-1(29),3,5,7(32),8,9,11,13,15(31),17,19,21(30),22, 23,25,27-hexadecaene) have been determined. The activation barriers for the racemization of carbodiimides 1 (6,7-dihydrodibenzo[d,h][1,3]diazonine), 2, and 3 have been determined. While 1 presents a relatively high barrier (17.4 kcal mol-1), 2 and 3 have very low activation barriers (between 5 and 7 kcal mol-1). We tentatively conclude that open-chain and large-ring carbodiimides racemize by nitrogen inversion or trans-rotation while medium-size cyclic carbodiimides racemize by cis-rotation.
- Molina, Pedro,Alajarín, Mateo,Sánchez-Andrada, Pilar,Carrió, Juan Server,Martínez-Ripoll, Martín,Anderson, J. Edgar,Jimeno, María Luisa,Elguero, José
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p. 4289 - 4299
(2007/10/03)
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- Palladium-Catalyzed Synthesis of Indoles from 2-Nitrostyrenes
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In the presence of palladium salts, oxidation of 2-nitrostyrenes 1 with nitrous acid alkyl esters 2 resulted in the formation of 2-nitrophenylacetaldehyde dialkyl acetals 3.Reductive cyclization of the acetals 3 with iron powder in acetic acid afforded indoles 5 in good yield.
- Izumi, Taeko,Soutome, Michihiko,Miura, Takashi
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p. 1625 - 1629
(2007/10/02)
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- POLYMERISATION OF INDOLE. PART 2. A NEW INDOLE TRIMER
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Treatment of indole (1) with toluene-p-sulphonic acid in benzene provided the 2,3'-indole trimer (4), a positional isomer of the well known 3,3'-indole trimer (3).The structure of the new trimer (4) was established by comparitive studies with the trimers (3) and (4).
- Ishii, Hisashi,Murakami, Keiko,Sakurada(nee Kawanabe), Eri,Hosoya, Katsuhiro,Murakami, Yasuoki
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p. 2377 - 2386
(2007/10/02)
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- Process for preparing urokinase complex
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This invention provides a process for preparing a fibrin-adsorable protein-urokinase complex characterized by reacting a protein adsorbable by fibrin with urokinase in the presence of a protein coupling reagent represented by the formula STR1 wherein R is phenylene or cycloalkylene, A is lower alkylene, B is lower alkylene which may optionally be substituted by lower alkylthio or phenyl-lower alkylthio, and l, m and n are each 0 or 1 provided that l, m and n are not 0 at the same time. The complex is useful as a thrombolytic agent.
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- Synthesis of Substituted Indoles via Meerwein Arylation
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A new method for the synthesis of substituted indoles is detailed.Meerwein arylation of 4- and 6-substituted 2-nitrobenzenediazonium chlorides with vinyl acetate or vinyl bromide and subsequent reductive cyclization of the resulting adducts affords the corresponding 6- and 4-substituted (CH3, OCH3, Cl, Br, CF3) indoles.The diazonium bisulfates of weakly basic 2-nitroanilines (4-Cl, 6-Br, 4-CF3) gave higher yields of Meerwein arylation adducts than the corresponding diazonium chlorides.Coupling of 2-nitrobenzenediazonium chloride with 2-acetoxy-1-alkenes followed byreductive cyclization affords 2-alkylindoles.
- Raucher, Stanley,Koolpe, Gary A.
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p. 2066 - 2069
(2007/10/02)
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- ALDEHYDE-ENAMINES FROM α-OXOCARBOXYLIC ACIDS. A FACILE AND GENERAL ROUTE TO ALDEHYDES VIA DECARBOXYLATION OF α-OXOCARBOXYLIC ACIDS CARRYING β-HYDROGENS
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When α-oxocarboxylic acids carrying β-hydrogens are treated with a secondary amine in boiling benzene with azeotropic removal of water, they decarboxylate quantitatively to form aldehyde-enamines which subsequently are hydrolyzed to the corresponding aldehydes in high yields.
- Stamos, Ioannis K.
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p. 459 - 462
(2007/10/02)
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- A FACILE ROUTE TO 1-ACETOXY- AND 1-METHOXYINDOLES
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A simple and practical synthetic method for 1-acetoxy and 1-methoxyindoles from 2-nitrotoluene is described.
- Somei, Masanori,Shoda, Toshiya
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p. 1523 - 1525
(2007/10/02)
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