cas 5381-20-4, 1-Benzothiophene-3-carbaldehyde

Articles about 5381-20-4Total 23 be found

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Unified Synthesis of Polycyclic Alkaloids by Complementary Carbonyl Activation**
A complementary dual carbonyl activation strategy for the synthesis of polycyclic alkaloids has been developed. Successful applications include the synthesis of tetracyclic alkaloids harmalanine and harmalacinine, pentacyclic indoloquinolizidine alkaloid nortetoyobyrine, and octacyclic β-carboline alkaloid peganumine A. The latter synthesis features a protecting-group-free assembly and an asymmetric disulfonimide-catalyzed cyclization. Furthermore, formal syntheses of hirsutine, deplancheine, 10-desbromoarborescidine A, and oxindole alkaloids rhynchophylline and isorhynchophylline have been achieved. Finally, a concise synthesis of berberine alkaloid ilicifoline B was completed.
Christmann, Mathias,He, Guoli,List, Benjamin
supporting information
p. 13591 - 13596
(2021/05/07)

Potent Inhibition of Nicotinamide N-Methyltransferase by Alkene-Linked Bisubstrate Mimics Bearing Electron Deficient Aromatics
Nicotinamide N-methyltransferase (NNMT) methylates nicotinamide (vitamin B3) to generate 1-methylnicotinamide (MNA). NNMT overexpression has been linked to a variety of diseases, most prominently human cancers, indicating its potential as a therapeutic target. The development of small-molecule NNMT inhibitors has gained interest in recent years, with the most potent inhibitors sharing structural features based on elements of the nicotinamide substrate and the S-adenosyl-l-methionine (SAM) cofactor. We here report the development of new bisubstrate inhibitors that include electron-deficient aromatic groups to mimic the nicotinamide moiety. In addition, a trans-alkene linker was found to be optimal for connecting the substrate and cofactor mimics in these inhibitors. The most potent NNMT inhibitor identified exhibits an IC50 value of 3.7 nM, placing it among the most active NNMT inhibitors reported to date. Complementary analytical techniques, modeling studies, and cell-based assays provide insights into the binding mode, affinity, and selectivity of these inhibitors.
Buijs, Ned,Campagna, Roberto,Emanuelli, Monica,Gao, Yongzhi,Innocenti, Paolo,Jespers, Willem,Martin, Nathaniel I.,Parsons, Richard B.,Sartini, Davide,Van Haren, Matthijs J.,Van Westen, Gerard J. P.,Zhang, Yurui,Gutiérrez-De-Terán, Hugo
p. 12938 - 12963
(2021/09/11)

Controlled Reduction of Nitriles by Sodium Hydride and Zinc Chloride
A new protocol for the controlled reduction of nitriles to aldehydes was developed using a combination of sodium hydride and zinc chloride. The iminyl zinc intermediates derived from aromatic nitriles could be further functionalized with allylmetal nucleophiles to afford homoallylamines. As the method allows the reduction of various aliphatic and aromatic nitriles with a concise procedure under milder reaction conditions and exhibits wide functional group compatibility, it is well suited for use in various opportunities in chemical synthesis.
Chiba, Shunsuke,Ong, Derek Yiren
p. 1369 - 1378
(2020/04/27)

Facile One-Pot Transformation of Primary Alcohols into 3-Aryl- and 3-Alkyl-isoxazoles and -pyrazoles
Various primary alcohols were smoothly transformed into 3-aryl- and 3-alkylisoxazoles in good yields in one pot by successive treatment with PhI(OAc) 2 in the presence of TEMPO, NH 2 OH, and then NCS, followed by reaction with alkynes in the presence of Et 3 N. Similarly, various primary alcohols were smoothly transformed into 3-aryl- and 3-alkylpyrazoles in good yields in one pot by successive treatment with PhI(OAc) 2 in the presence of TEMPO, PhNHNH 2, and then NCS and decyl methyl sulfide, followed by reaction with alkynes in the presence of Et 3 N. Thus, both 3-aryl- and 3-alkylisoxazoles, and 3-aryl- and 3-alkylpyrazoles could be prepared from readily available primary alcohols in one pot under transition-metal-free conditions.
Kobayashi, Eiji,Togo, Hideo
p. 3723 - 3735
(2019/09/30)

PPAR (peroxisome proliferator-activated receptor) agonist and application thereof to treatment of senile dementia and other diseases
The invention relates to a compound, namely a gamma-subtype peroxisome proliferator-activated receptor (PPAR) agonist. In addition, the invention discloses a medicinal component and a preparation containing the compound and application of such the gamma-subtype PPAR agonist.
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Paragraph 0381; 0387-0389

(2018/07/30)

Visible light photocatalysis with CBr4: A highly selective aerobic photooxidation of methylarenes to aldehydes
A metal-free, operationally simple and efficient means of aerobic photooxidation of methylarenes to aromatic aldehydes at room temperature employing visible light photocatalysis with CBr4 is reported. The reaction is highly selective as it proceeds without any over oxidation to carboxylic acids. The utilisation of visible light and molecular oxygen is inexpensive, readily available, non-toxic and the sustainable reagents make the protocol compatible with green chemistry demands. A plausible mechanism for the formation of aldehydes from methylarenes is also provided.
Tripathi, Shubhangi,Singh, Sachchida N.,Yadav, Lal Dhar S.
p. 14547 - 14551
(2016/02/19)

Palladium-catalyzed synthesis of aldehydes from aryl halides and tert-butyl isocyanide using formate salts as hydride donors
An efficient one-pot palladium-catalyzed hydroformylation of aryl halides to produce aromatic aldehydes has been achieved, employing tert-butyl isocyanide as a C1 resource and formate salt as a hydride donor without any additional bases. Characterized by its mild reaction conditions, easy operation and lower toxicity, this reaction can tolerate a wide array of functional groups with moderate to excellent yields.
Zhang, Ying,Jiang, Xiao,Wang, Jin-Mei,Chen, Jing-Lei,Zhu, Yong-Ming
p. 17060 - 17063
(2015/03/30)

Palladium-catalyzed formylation of aryl halides with tert -butyl isocyanide
A novel palladium-catalyzed formylation of aryl halides with isocyanide in the presence of Et3SiH has been demonstrated, which provides a strategy toward important aldehydes with moderate to excellent yield. The advantage of this reaction includes milder conditions, convenient operation, lower toxicity, and wide functional group tolerance.
Jiang, Xiao,Wang, Jin-Mei,Zhang, Ying,Chen, Zhong,Zhu, Yong-Ming,Ji, Shun-Jun
supporting information
p. 3492 - 3495
(2014/07/21)

One-pot transformation of methylarenes into aromatic aldehydes under metal-free conditions
On the basis of studies of the transformation of benzylic bromides into the corresponding aromatic aldehydes by treatment with N-methylmorpholine N-oxide, various methylarenes were treated either with DBDMH in the presence of AIBN in acetonitrile at reflux (Method A) or with NBS in CCl4 under irradiation with a tungsten lamp at 30 °C (Method B), followed by treatment with N-methylmorpholine N-oxide to provide aromatic aldehydes in good yields. These methods could be adopted in one-pot transformations of methylarenes into aromatic aldehydes under conditions free of less toxic reagents and transition metals. Copyright
Tabata, Masayuki,Moriyama, Katsuhiko,Togo, Hideo
p. 3402 - 3410
(2014/06/09)

Enantioselective straightforward access to benzo[b]thiophene analogs of Azatoxin
Horner-Wadsworth Emmons olefination followed by asymmetric hydrogenation allowed the first synthetic access to the chiral thiotryptophan with good enantiomeric excess. Oxazolidinone formation followed by a Pictet-Spengler condensation provided the benzothiophenic analog of Azatoxin.
Gracia, Stéphanie,Marion, Cédric,Rey, Jullien,Popowycz, Florence,Pellet-Rostaing, Stéphane,Lemaire, Marc
scheme or table
p. 3165 - 3168
(2012/08/08)

Palladium-catalyzed reductive carbonylation of aryl bromides with phosphinite ligands
A palladium-catalyzed reductive carbonylation of aryl bromides into the corresponding aryl aldehydes has been described using synthesis gas in the presence of phosphinite ligands. Several products have been synthesized in moderate to good yields (35-97 %) under mild reaction conditions. Copyright
Neumann, Helfried,Kadyrov, Renat,Wu, Xiao-Feng,Beller, Matthias
p. 2213 - 2216
(2012/10/29)

A palladium-catalyzed approach to polycyclic sulfur heterocycles
(Chemical Equation Presented) The synthesis of a variety of polycyclic thiophenes and benzothiophenes is accomplished via a palladium-catalyzed domino ortho-alkylation/direct arylation reaction. An examination of the intramolecular direct arylation of thi
Martins, Andrew,Lautens, Mark
scheme or table
p. 8705 - 8710
(2009/04/11)

Design, synthesis, and evaluation of potential inhibitors of brassinin glucosyltransferase, a phytoalexin detoxifying enzyme from Sclerotinia sclerotiorum
Sclerotinia sclerotiorum is a fungal pathogen, which causes stem rot in crucifer crops and in several other plant families resulting in enormous yield losses all over the world. Brassinin is a phytoalexin produced by crucifer plants as part of a general d
Pedras, M. Soledade C.,Hossain, Mohammad
p. 5981 - 5996
(2008/03/27)

On the functionalization of [2.2](1,4)phenanthrenoparacyclophane
Two routes for preparing functionalized [2.2](1,4) phenanthrenoparacyclophanes are described: either the parent system 2 is subjected to electrophilic substitution (bromination, Friedel-Crafts acylation, Rieche formylation: preparation of 5, 6, 7, 11 and 12) or the desired substituents are incorporated in the early stages of the synthesis by the preparation of the corresponding functionalized styryl paracyclophanes and their photocyclization to the respective phenanthrenocyclophanes. By these specific routes various bronudes (22a,b), ethers (28a-c) and phenols (29a,b) were synthesized. The latter derivatives, on oxidation, furnish para-(31) and ortho-quinonophanes (30, 32, 33), useful substrates for the preparation of cyclophanes containing phenazine subunits (36). The stilbene → phenanthrene photocyclization can also be employed for the preparation of benzothiophenophanes, e.g. 43 and 44, from the respective precursors. Wiley-VCH Verlag GmbH & Co. KGaA, 2007.
Hopf, Henning,Hucker, Joachim,Ernst, Ludger
p. 1891 - 1904
(2008/02/06)

The interaction of heteroaryl-acrylates and alanines with phenylalanine ammonia-lyase from parsley
Acrylic acids and alanines substituted with heteroaryl groups at the β-position were synthesized and spectroscopically characterized (UV, HRMS, 1H NMR, and 13C NMR spectroscopy). The heteroaryl groups were furanyl, thiophenyl, benzofuranyl, and benzothiophenyl and contained the alanyl side chains either at the 2- or 3-positions. While the former are good substrates for phenylalanine ammonia lyase (PAL), the latter compounds are inhibitors. Exceptions are thiophen-3-yl-alanine, a moderate substrate and furan-3-yl-alanine, which is inert. Possible reasons for these exceptions are discussed. Starting from racemic het eroaryl-2-alanines their D-enantiomers were prepared by using a stereodestructive procedure. From the heteroaryl-2- acrylates, the L-enantiomers of the heteroaryl-2-alanines were prepared at high ammonia concentration. These results can be best explained by a Friedel - Crafts-type electrophilic attack at the aromatic part of the substrates as the initial step of the PAL reaction.
Paizs, Csaba,Katona, Adrian,Retey, Janos
p. 2739 - 2744
(2008/02/03)

Design, synthesis, and antifungal activity of inhibitors of brassilexin detoxification in the plant pathogenic fungus Leptosphaeria maculans
Potential inhibitors of Leptosphaeria maculans mediated detoxification of the phytoalexin brassilexin were designed and synthesized based on the planar heteroaromatic structure of isothiazolo[5,4-b]indole. Screening of these compounds for inhibition of br
Pedras, M. Soledade C.,Suchy, Mojmir
p. 714 - 723
(2007/10/03)

A general and efficient method for the formylation of aryl and heteroaryl bromides
(Chemical Equation Presented) The key to the general and efficient palladium-catalyzed formylation of aryl and heteroaryl bromides is the use of the di-1-adamantyl-n-butylphosphane (cataC-Xium A) as ligand. Low pressure of the synthesis gas and appropriate choice of the base are also important for high yields (up to 99%) of a broad range of (hetero)aromatic aldehydes at unprecedented low catalyst concentrations (see scheme; TMEDA= N,N,N′,N′-tetramethylethylenediamine).
Klaus, Stefan,Neumann, Helfried,Zapf, Alexander,Struebing, Dirk,Huebner, Sandra,Almena, Juan,Riermeier, Thomas,Gross, Peter,Sarich, Martin,Krahnert, Wolf-Ruediger,Rossen, Kai,Beller, Matthias
p. 154 - 158
(2007/10/03)

Synthesis of aromatic aldehydes by oxidative hydroxymethylation
A new high yield method for the synthesis of aromatic aldehydes has been developed. The procedure is based on an acid catalyzed hydroxymethylation of an arene substrate by paraformaldehyde with concurrent selective oxidation of the intermediate aromatic carbinol by 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) to the aldehyde product.
Branytska, Oiena,Neumann, Ronny
p. 1575 - 1576
(2007/10/03)

Synthesis of novel chiral thiophene-, benzothiophene- and benzofuran-oxazoline ligands and their use in the enantioselective Pd-catalyzed allylation
Novel thiophene, benzothiophene and benzofuran-oxazoline ligands 6-11 containing a diphenylphosphino group at different positions of the heterocyclic skeleton have been prepared and used in the enantioselective allylation. The advantage of these new ligands is their easy accessibility and their high reactivity. The best results were obtained with ligand 9 to give the product 13 in 97.0% ee with 92% yield in 2 hours at 0°C.
Tietze, Lutz F.,Lohmann, J. Klaas
p. 2083 - 2085
(2007/10/03)

Dehydroamino acids
Compounds of formula 1 and 1-1, wherein R1 is hydrogen, hydroxy, amino or halogen, R2 is hydrogen, hydroxy, or halogen and R3 is hydrogen (Formula 1) or R1 is hydrogen and R2 and R3 taken together with the ethenylene group connecting them form phenyl, pyrrole, pyrroline, oxopyrroline, pyrazole, triazole, or imidazole (Formula 1-1), A is R4 R5 are hydrogen, methyl, ethyl or halogen except that R4 r5 cannot both be hydrogen; and 1) B is hydrogen, or lower alkyl; or 2) B is where R6 R7 R8 and R9 are independently hydrogen, hydroxy, aminosulfonyl, halogen, lower alkoxy, cyano, amino, lower alkyl, lower alkyl amino, or nitro; or 3) B is where R10 is hydrogen, hydroxy, halogen, or lower alkyl and C is a five- or six- membered ring with 0 to 3 heteroatoms which heteroatoms are selected from nitrogen, oxygen, and sulfur, which ring may be unsubstituted or mono- or di- substituted with lower alkyl, cycloalkyl, amino, or substituted amino; 4) B is where X and Y are independently methylene or nitrogen; or 5) B is where at leat one of T, U, V, or W is nitrogen, and any of T, U, V or W which is carbon may be substituted with lower alkyl, lower alkyl amino, lower alkoxy, hydroxy, aminosulfonyl, halogen, cyano, amino, or nitro; or 6) B is where Y is carbon or nitrogen; or 7) B is a five-membered aromatic ring with 1 to 3 heteratoms selected from nitrogen, oxygen, and sulfur which ring may be unsubstituted or mono- or di-substituted with lower alkyl, cycloalky, trifluoroloweralkyl, amino, halogen, substituted amino, or which ring may be fused with a 5 or 6 membered aromatic ring containing 0 to 3 heteroatoms which heteroatoms are selected from nitrogen, oxygen, and sulfur; and pharmaceutically acceptable salts thereof, and related prodrugs, pharmaceutical compositions and methods of treatment, which compounds are useful for treating psoriasis.
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(2008/06/13)

Dihydropyridines useful in the treatment of angina and stroke
This invention provides certain substituted dihydropyridines, their pharmaceutical formulations, and their use for causing vasodilation in mammals.
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(2008/06/13)

OUVERTURE PAR LES ORGANOLITHIENS D'ISOTHIAZOLES ET ISOSELENAZOLES HETEROCONDENSES
The ring-opening of bi- and tricyclic systems bearing an isothiazole or isoselenazole ring fused to a thiophene or a selenophene ring was studied by their reaction with methyl lithium.
Onyamboko, N. V.,Weber, R.,Fauconnier, A.,Renson, M.
p. 53 - 60
(2007/10/02)

Studies on drug synthesis with thionaphthene-3-aldehyde
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Neidlein,Seel
p. 834 - 841
(2007/10/07)

Chemical Properties

Appearance/Colour :yellow to brown crystalline powder

Melting Point: 53-57 °C(lit.)

Boiling Point: 303.2 °C at 760 mmHg

Flash Point:137.2 °C

Density: 1.3 g/cm³

Storage Temp.:under inert gas (nitrogen or Argon) at 2–8 °C

Vapor Pressure: 0.000944mmHg at 25°C

Refractive Index: 1.719

PSA: 45.31000

LogP: 2.71380

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Article Database

5381-20-4

Articles about 5381-20-4Total 23 be found

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Chemical Properties

Appearance/Colour :yellow to brown crystalline powder

Melting Point: 53-57 °C(lit.)

Boiling Point: 303.2 °C at 760 mmHg

Flash Point:137.2 °C

Density: 1.3 g/cm³

Storage Temp.:under inert gas (nitrogen or Argon) at 2–8 °C

Vapor Pressure: 0.000944mmHg at 25°C

Refractive Index: 1.719

PSA: 45.31000

LogP: 2.71380

Global suppliers and manufacturers of 5381-20-4total 95 suppliers on LookChem

Article Database

5381-20-4

Articles about 5381-20-4Total 23 be found

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Chemical Properties

Appearance/Colour :yellow to brown crystalline powder

Melting Point: 53-57 °C(lit.)

Boiling Point: 303.2 °C at 760 mmHg

Flash Point:137.2 °C

Density: 1.3 g/cm3

Storage Temp.:under inert gas (nitrogen or Argon) at 2–8 °C

Vapor Pressure: 0.000944mmHg at 25°C

Refractive Index: 1.719

PSA: 45.31000

LogP: 2.71380

Global suppliers and manufacturers of 5381-20-4total 95 suppliers on LookChem

Density: 1.3 g/cm³