cas 17282-40-5, 1-(2-ETHOXY-2-OXOETHYL)PYRIDINIUM BROMIDE

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Design, Synthesis, and Biological Evaluation of 6-Substituted-3-(4-methanesulfonylphenyl)-4-phenylpyran-2-ones: A Novel Class of Diarylheterocyclic Selective Cyclooxygenase-2 Inhibitors
A group of 6-alkyl (alkoxy or alkylthio)-4-aryl-3-(4-methanesulfonylphenyl)pyran-2-ones (14a-v), possessing either a H or F substituent at the para-position of the C-4 phenyl ring, were designed for evaluation as selective cyclooxygenase-2 (COX-2) inhibit
Rao, P.N. Praveen,Amini, Mohsen,Li, Huiying,Habeeb, Amgad G.,Knaus, Edward E.
p. 4872 - 4882
(2003)
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Synthesis of 2-methyl-1,4-naphthoquinones with higher gamma-glutamyl carboxylase activity than MK-4 both in vitro and in vivo
Vitamin K is the collective term for compounds that share a 2-methyl-1,4-naphthoquinone ring, but differ in the side-chain at the 3-position. We synthesized novel 2-methyl-1,4-naphthoquinone derivatives with different side chain length at the 3-position. Derivatives with C-14 and C-16 tails showed the highest in vitro bioactivity resulting in 2.5 and 2-fold higher carboxylated osteocalcin synthesis in MG63 cells than menaquinone-4 (MK-4, form of vitamin K2). Longer side chain lengths resulted in lower bioactivity. The in vivo vitamin K activity of the C-14 tail derivative was further tested in WKY rats receiving a vitamin K-deficient diet that resulted in a 40% decrease of prothrombin activity. The C-14 tail derivative was able to counteract the effects on vitamin K deficiency induced by the diet and resulted in the complete restoration of prothrombin activity. Compared to naturally occurring forms of vitamin K, synthetic vitamin K derivatives may have higher bioactivity and different pharmacological characteristics that are more favorable for use as supplements or in clinical settings.
Vermeer, Cees,van ‘t Hoofd, Cynthia,Knapen, Marjo H.J.,Xanthoulea, Sofia
p. 208 - 211
(2017)
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Deep oxidative desulfurization of fuels in the presence of Br?nsted acidic polyoxometalate-based ionic liquids
Polyoxometalate-based ionic liquid hybrid materials with a pyridinium cation, containing Br?nsted acid sites, were synthesized and used as catalysts for the oxidation of model and real diesel fuels. Keggin-type polyoxometalates with the formulae [PMo12O40]3?, [PVMo11O40]4?, [PV2Mo10O40]4?, [PW12O40]3? were used as anions. It was shown that increasing the acid site strength leads to an increase of dibenzothiophene conversion to the corresponding sulfone. The best results were obtained in the presence of a catalyst, containing a nicotinic acid derivative as cation and phosphomolybdate as anion. The main factors affecting the process consisting of catalyst dosage, temperature, reaction time, oxidant dosage were investigated in detail. Under optimal conditions full oxidation of dibenzothiophene and more than a 90% desulfurization degree of real diesel fuel (initial sulfur content of 2050 ppm) were obtained (the oxidation conditions: NK-1 catalyst, molar ratio H2O2:S 10:1, molar ratio S:Mo 8:1, 1 mL MeCN, 70 °C, 1 h). The synthesized catalysts could be used five times with a slight decrease in activity.
Akopyan, Argam,Eseva, Ekaterina,Glotov, Aleksandr,Kedalo, Anastasia,Polikarpova, Polina,Vutolkina, Anna
(2020)
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Fluorescent single-walled carbon nanotubes following the 1,3-dipolar cycloaddition of pyridinium ylides
Pyridinium ylides generated from simple Kroehnke salts undergo a 1,3-dipolar cycloaddition to single-walled carbon nanotubes (SWNTs) offering a simple and convenient method for the covalent modification of carbon nanotubes. The indolizine functionalized SWNTs generated, emit blue light when excited at 335 nm. The location and distribution of the functional groups was determined by AFM using electrostatic interactions with gold nanoparticles. While resonance Raman spectroscopy showed that the 1,3-dipolar cylcloaddition of the pyridinium ylides to the nanotube surface was selective for metallic and large diameter semiconducting SWNTs. The indolizine functionalized SWNTs were further characterized using FTIR, UV-vis-NIR, TGA-MS, and XPS.
Bayazit, Mustafa K.,Coleman, Karl S.
p. 10670 - 10676
(2009)
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Unified Synthesis of Azepines by Visible-Light-Mediated Dearomative Ring Expansion of Aromatic N-Ylides
Herein, we report a unified approach to azepines by dearomative photochemical rearrangement of aromatic N-ylides. Deprotonation of quaternary aromatic salts with 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) or N,N,N′,N'-tetramethylquanidine (TMG) under visible light irradiation provides mono- and polycyclic azepines in yields up to 98%. This ring-expansion presents a new mode of access to functionalized azepines from N-heteroarenes using two straightforward steps and simple starting materials.
Mailloux, Matthew J.,Fleming, Gabrielle S.,Kumta, Shruti S.,Beeler, Aaron B.
supporting information
p. 525 - 529
(2021/01/26)

-Annulation of gem-Difluoroalkenes and Pyridinium Ylides: Access to Functionalized 2-Fluoroindolizines
A [3 + 2]-annulation of gem-difluoroalkenes and pyridinium ylides was developed employing ambient air as the sole oxidant in an open-vessel manner, affording a series of multifunctionalized 2-fluoroindolizines in moderate to good yields. In this reaction, gem-difluoroalkene acts as a C2 synthon and entirely avoids the competitive addition-elimination process, which provides facile access to 2-fluoroindolizines.
Zhang, Jun-Qi,Hu, Dandan,Song, Jinyu,Ren, Hongjun
p. 4646 - 4660
(2021/04/06)

Synthetic method and application of indolizine compounds
A synthetic method of the indolizine compound comprises the following steps: mixing a benzopyrone derivative, a bromopyridinium salt derivative, alkali and a solvent in a 10ml round-bottom flask, andstirring the mixture for 2-48 hours at the temperature of 25 DEG C and 100 DEG C; after the reaction is finished, purifying the crude product through silica gel chromatography to obtain a target compound with a structural formula shown as the formula I.
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Paragraph 0034; 0038-0040

(2020/11/26)

DMAP-Catalyzed Annulation Approach for Modular Assembly of Furan-Fused Chromenes
With a tandem DMAP-catalyzed reaction between o-AQM, in which it is generated in situ from propargylic amine, and acyl carbene surrogate (from pyridinium ylide), a variety of polyarylated chromenes are assembled in good yields. This process does not require transition-metal catalyst and exhibits easy manipulation of the arene group and good functional group compatibility, particularly the -Br group which can be further transformed to other functionalities by cross-coupling reactions. The modular feature of o-AQM substrates and the simple operation procedures add further advantages to this synthetic method.
He, Xinwei,Li, Ruxue,Choy, Pui Ying,Liu, Tianyi,Wang, Junya,Yuen, On Ying,Leung, Man Pan,Shang, Yongjia,Kwong, Fuk Yee
supporting information
p. 9444 - 9449
(2020/12/21)

External oxidant-free oxidation/[3+2] cycloaddition/aromatization cascade: Electrochemical synthesis of polycyclic N-heterocycles
Here, we describe an efficient and environmentally friendly synthesis of polycyclic N-heterocycles under electrochemical external oxidant-free conditions. The extent of the sequential electrochemical oxidative aromatization can be regulated with the assistance of redox mediators.
Wang, Qiang,Yuan, Ting,Liu, Qiang,Xu, Yong,Xie, Guanqun,Lv, Xin,Ding, Shujiang,Wang, Xiaoxia,Li, Chen
supporting information
p. 8398 - 8401
(2019/07/22)

Method of preparing 4,5-disubstituted 1,2,3-triazole with pyridinium salt
The invention relates to a method of synthesizing a 4,5-disubstituted 1,2,3-triazole compound. The method comprises the following step of by taking pyridine, halohydrocarbon, sulfonic ester, aldehydeand sodium azide as raw materials, and performing room-temperature reaction with a one-pot method. The synthetic method does not need a metal-containing catalyst, has the advantages of high yield of synthetic products, mild reaction condition, good functional group compatibility and the like, is simple in operation step, mild in reaction condition and wide in application range of a substrate, hasinnovativeness and a potential practical value and is suitable for industrial production.
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Paragraph 0021-0034; 0041-0042

(2018/09/08)

Visible-Light-Induced Carbo-2-pyridylation of Electron-Deficient Alkenes with Pyridinium Salts
A simple and practical visible-light-induced carbo-2-pyridylation of electron-deficient alkenes with readily available N-benzoylmethylpyridinium bromides is reported. More than 40 examples are presented and proceed in greater than 80 % yield (on average)
Hu, Rong-Bin,Sun, Shuai,Su, Yijin
supporting information
p. 10877 - 10880
(2017/08/30)

Transition-Metal-Free Synthesis of Indolizines from Electron-Deficient Alkenes via One-Pot Reaction Using TEMPO as an Oxidant
A one-pot method for the synthesis of multisubstituted indolizines from α-halo carbonyl compounds, pyridines, and electron-deficient alkenes is reported. The oxidative dehydrogenation reaction takes place under transition-metal-free conditions using TEMPO as an oxidant. This protocol uses ready available starting materials in a convenient procedure under mild reaction conditions.
Shi, Fei,Zhang, Yu,Lu, Zhaole,Zhu, Xiaolei,Kan, Weiqiu,Wang, Xiang,Hu, Huayou
p. 413 - 420
(2016/01/28)

Pinene-derived monodentate phosphoramidites for asymmetric hydrogenation
Phosphoramidite ligands based on pinene-derived chiral amines have been prepared by a straightforward procedure in good yields. The key step of the synthetic protocol is a stereoselective hydrogenation of annulated pinene-pyridine derivatives leading to (diastereoisomeric) secondary amines that were separated and treated with different chlorophosphites to yield the envisaged phosphoramidites. The absolute configurations of the ligands were assigned on the basis of NMR analyses and corroborated by X-ray diffraction analysis of a borane adduct of a typical ligand. The new ligands were employed in the asymmetric hydrogenation of imines and olefins. The iridium-catalyzed hydrogenation of imines provided up to 81?% ee, whereas in the rhodium-catalyzed hydrogenation of functionalized olefins enantioselectivities of up to 99?% ee were achieved. In this particular application, the different chiral elements of the ligand structure led to synergistic effects and the enantioselectivity is dominated by the chiral diol moiety.
Schmitz, Christian,Leitner, Walter,Franciò, Giancarlo
p. 2889 - 2901
(2015/04/27)

One-pot synthesis of indolizine via 1,3-dipolar cycloaddition using a sub-equivalent amount of K2Cr2O7 as an efficient oxidant under base free conditions
A one-pot method for synthesizing multi-substituted indolizines from α-halo-carbonyl compounds, pyridines and electron deficient alkenes was developed. A sub-equivalent amount of potassium dichromate was used as an oxidant under base free conditions. The transformation developed should be of economic efficiency.
Wang, Chao,Hu, Huayou,Xu, Juanfang,Kan, Weiqiu
p. 41255 - 41258
(2015/05/20)

CERTAIN PROTEIN KINASE INHIBITORS
Provided are certain EGFR mutant selective inhibitors, pharmaceutical compositions thereof, and methods of use therefor.
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Paragraph 00314-00316

(2016/01/01)

One-pot two-step synthesis of 1-(ethoxycarbonyl)indolizines via pyridinium ylides
Pyridinium salts Py+-CH2-EWG (EWG = CO2Et, CONEt2, CN, COMe, COPh) reacted with Michael acceptors Ar-CH=C(CO2Et)(Acc) (Acc = CO2Et, COMe, SO2Me, CONH2) at ambient temperature in the presence of base to give [3 + 2]-cycloadducts by stepwise [3 + 2]-cycloaddition of the intermediate pyridinium ylides. Treatment of the crude reaction mixtures with 1 equiv. of chloranil and atmospheric oxygen in the presence of sodium hydroxide gave 1-(ethoxycarbonyl)indolizines by dehydrogenation and elimination of the acceptor group (Acc). A good yield of indolizine was also obtained from Py +-CH2CN and iPr-CH=C(CO2Et)2, which indicates that this method is not restricted to aromatic Michael acceptors. Structurally related isoquinolinium salts react with Michael acceptors analogously to give pyrrolo[2,1-a]isoquinolines.
Allgaeuer, Dominik S.,Mayr, Herbert
supporting information
p. 6379 - 6388
(2013/10/21)

COMPOUND FOR AN ORGANIC PHOTOELECTRIC DEVICE, ORGANIC PHOTOELECTRIC DEVICE INCLUDING THE SAME, AND DISPLAY DEVICE INCLUDING THE ORGANIC PHOTOELECTRIC DEVICE
A compound for an organic photoelectric device, an organic photoelectric device including the same, and a display device including the organic photoelectric device, the compound being represented by the following Chemical Formula 1:
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Page/Page column 69-70

(2013/02/27)

Pd-Catalyzed C-3 functionalization of indolizines via C-H bond cleavage
New transition metal-catalyzed methods for the arylation of indolizines by the direct cleavage of C-H bonds have been developed. A wide range of aryltrifluoroborate salts react with indolizines in the presence of Pd(OAc) 2 catalyst and AgOAc oxidant to give the arylated indolizines in high yields. Both electron-donating and electron-withdrawing groups perform smoothly while bromide and chlorine substituents are tolerated. In addition, the indolizines display similar reactivities in the Pd-catalyzed reaction with 3-phenylpropiolic acid to afford the corresponding C-3 alkynylated indolizines. These methods allow the direct functionalization of indolizines in one step.
Zhao, Baoli
supporting information; experimental part
p. 7108 - 7119
(2012/09/25)

Convenient synthesis of 2-aryl-1-haloindolizines from pyridinium salts and 2-aryl-1,1-dihaloalk-1-enes
2-Aryl-1-haloindolizines were synthesized from pyridinium salts and 2-aryl-1,1-dihaloalk-1-enes using a DBU/THF system. 2-Aryl-1,1-dihaloalk-1-enes containing electron-withdrawing or -donating groups were efficiently converted into the corresponding 2-aryl-1-haloindolizines in moderate to excellent yields. Georg Thieme Verlag Stuttgart.
Yang, Yiwen,Kuang, Chunxiang,Jin, Hui,Yang, Qing
supporting information; experimental part
p. 3447 - 3452
(2011/12/04)

Synthesis of zwitterionic salts of pyridinium-meldrum acid and barbiturate through unique four-component reactions
An efficient synthetic procedure for the preparation of the unusual charge-separated pyridinium-Meldrum acid and N,N-dimethylbarbiturate acid zwitterionic salts was developed though a unique one-pot fourcomponent reaction involving pyridine, aromatic aldehyde, Meldrum acid or N,N-dimethylbarbituric acid, and p-nitrobenzyl bromide in acetonitrile. By varying combinations of four components involving nitrogencontaining heterocycles, we conveniently established reactiveα-halomethylene compounds, aldehydes and β-dicarbonyl compounds a library of zwitterionic salts.
Wang, Qi-Fang,Hui, Li,Hou, Hong,Yan, Chao-Guo
supporting information; experimental part
p. 260 - 265
(2010/08/05)

Biodegradable pyridinium ionic liquids: Design, synthesis and evaluation
A range of ionic liquids (ILs) with a pyridinium cation were synthesised and their biodegradability was evaluated using the CO2 Headspace test (ISO 14593). ILs bearing an ester side chain moiety were prepared from either pyridine or nicotinic acid and showed high levels of biodegradation under aerobic conditions and can be classified as 'readily biodegradable'. In contrast, pyridinium ILs with alkyl side chains showed significantly lower levels of biodegradability in the same test. The utility of the biodegradable IL 6c as a reaction solvent for the Diels-Alder reaction was also investigated.
Harjani, Jitendra R.,Singer, Robert D.,Garcia, M. Teresa,Scammells, Peter J.
experimental part
p. 83 - 90
(2010/04/22)

NEW AMINOINDOLIZINES, DYEING COMPOSITION COMPRISING AT LEAST ONE AMINOINDOLIZINE, METHODS AND USES THEREOF
A new class of chemical entities chosen from aminoindolizines of formula (I), acid addition salts thereof, and solvates thereof: their use for dyeing keratin fibers, including human keratin fibers such as the hair; dyeing compositions comprising such chemical entities; and to kits containing compositions comprising those chemical entities.
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(2009/10/01)

Synthesis of 18F-labeled cyclooxygenase-2 (COX-2) inhibitor as a potential PET imaging agent
A new PET tracer for COX-2 imaging, the 6-ethoxy-3-(4- methanesulfonylphenyl)-4-(4-[18F]fluorophenyl)pyran-2-one ([ 18F]EFMP), was synthesized. For F-18 radiolabeling, a trimethylammonium precursor and a brominated precursor were syn
Tian, Haibin,Lee, Zhenghong
p. 583 - 593
(2007/10/03)

A novel coupling 1,3-dipolar cycloaddition sequence as a three-component approach to highly fluorescent indolizines
Indolizines 4 and biindolizines 6 can be synthesized in moderate yields in a consecutive one-pot three-component process by a coupling/1,3-dipolar cycloaddition sequence of a (hetero)arenecarbonyl chloride 1, a terminal alkyne 2, and a suitable 1-(2-oxoet
Rotaru, Alexandra V.,Druta, Ioan D.,Oeser, Thomas,Müller, Thomas J. J.
p. 1798 - 1812
(2007/10/03)

Synthesis of new chiral 2,2′-bipyridine ligands and their application in Copper-catalyzed asymmetric allylic oxidation and cyclopropanation
A series of modular bipyridine-type ligands 1 and 3-9 has been synthesized via a de novo construction of the pyridine nucleus. The chiral moieties of these ligands originate from the isoprenoid chiral pool, namely, β-pinene (10 → 1), 3-carene (14 → 3 and 5), 2-carene (28 → 4), α-pinene (43 → 6-8), and dehydropregnenolone acetate (48 → 9), respectively. Copper(I) complexes, derived from these ligands and (TfO)2Cu (1 mol%) upon an in situ reduction with phenylhydrazine, exhibit good enantioselectivity (up to 82% ee) and unusually high reaction rate (typicaly 30 min at room temperature) in allylic oxidation of cyclic olefins (52 → 53). Copper-catalyzed cyclopropanation proceeded with ≤76% enantioselectivity and ～3:1 to 99:1 trans/cis-diastereoselectivity (54 → 55 + 56). The level of the asymmetric induction is discussed in terms of the ligand architecture that controls the stereochemical environment of the coordinated metal.
Malkov, Andrei V.,Pernazza, Daniele,Bell, Mark,Bella, Marco,Massa, Antonio,Teply, Filip,Meghani, Premji,Kocovsky, Pavel
p. 4727 - 4742
(2007/10/03)

Synthesis and optical properties of a series of pyrrolopyridazine derivatives: Deep blue organic luminophors for electroluminescent devices
We describe a systematic study of a series of eight blue light-emitting molecules which can be prepared in one step from inexpensive commercial starting materials. The relative luminescence quantum yield can be as high as 84% and the heterocycles are luminescent in the condensed state, either as solids or as oils, indicating that there is no self-quenching in this system. The last observation augurs well for these heterocycles being useful in the fabrication of deep blue light-emitting devices.
Cheng, Yang,Ma, Bin,Wudl, Fred
p. 2183 - 2188
(2007/10/03)

Study of the reactivity of substituted phthalic acids and anhydrides in condensation reactions with N-carboxymethylpyridinium salts and the synthesis of novel N-(1H-indene-1,3(2H)-dion-2-yl)pyridinium betaines
Reaction of substituted phthalic acids or their anhydrides (including pyromellitic dianhydride) with salts of N-carboxymethylpyridinium and substituted N-carboxymethylpyridinium in the presence of acetic anhydride and triethylamine in acetonitrile or acetic acid solutions gave a series of novel N-(1H-indene-1,3(2H)-dion-2-yl)pyridinium betaines. Electron acceptor substitutents in the phthaloyl and pyridine rings were found to increase and electron donor substituents - to decrease the reactivity. 1999 Kluwer Academic/Plenum Publishers.
Neilands,Shebenina,Pukitis
p. 1443 - 1450
(2007/10/03)

Reaction of N-alkylpyredinium salts with phosphorus trichloride
1-Alkylpyridinium bromides 1 having activated N-methylene group react with phosphorus trichloride to give N-(dichlorophosphinomethylene)pyridinium ylides 2. The site of the reaction in 1,2-dialkylpyridinium halides 3 under these conditions is determined by the relative activation of 1- and 2-methylene groups; in the absence of sufficient activation of N-methylene group, reaction occurs at the 2-methylene group to give dichlorophosphinylated anhydrobases 5 and 11. 1,4-Dialkylpyridinium bromide 13 behaves analogously to give the corresponding dichlorophosphinylated anhydrobase 14.
Bansal, Raj K.,Gupta, Neelima,Gupta, Rakhi,Pandey, Garima,Agarwal, Mamta
p. 121 - 130
(2007/10/03)

Equilibrium Acidities and Homolytic Bond Dissociation Energies of the Acidic C-H Bonds in N-Substituted Trimethylammonium and Pyridinium Cations
Equilibrium acidities (pKHAs) of the cations in sixteen N-substituted trimethylammonium salts, one N-phenacylquinuclidinium salt, eight N-substituted pyridinium salts, and N-(ethoxycarbonyl)-isoquinolinium bromide, together with the oxidation potentials of their conjugate bases, have been determined in dimethyl sulfoxide (DMSO) solution.The acidifying effects of the α-trimethylammonium groups (α-Me3N+) and the α-pyridinium groups (α-PyN+) on the adjacent acidic C-H bonds in these cations were found to average about 10 and 18 pKHA units, respectively, in DMSO.The homolytic bond dissociation energies of the acidic C-H bonds in these cations, estimated by the combination of the equilibrium acidities with the oxidation potentials of their corresponding conjugate bases (ylides), show that the α-trimethylammonium groups destabilize adjacent radicals by 2-6 kcal/mol, whereas α-pyridinium groups stabilize adjacent radicals by 3-6 kcal/mol.The effects of α-pyridinium groups on the stabilization energies of the radicals derived from these cations were found to be ca. 4-10 kcal/mol smaller than those of the corresponding phenyl groups, whereas their effects on the equilibrium acidities of the cations were 5.4-13.1 pKHA units larger.The pKHA value of tetramethylammonium cation (Me4N+) was estimated by extrapolation to be about 42 in DMSO.
Zhang, Xian-Man,Bordwell, Frederick G.,Puy, Michael Van Der,Fried, Herbert E.
p. 3060 - 3066
(2007/10/02)

Ester-containing quaternary pyridinium salts
New ester-containing quaternary pyridinium salts are provided having advantageous utility as charge control agents in electrostatographic toners and developers. The salts have the structure: STR1 wherein R1 is alkyl or aryl, X is --CH2 --n, Y is hydrogen, alkyl, alkoxy or halogen, Z? is an anion and n is an integer from 1 to 6. Such ester-containing quaternary pyridinium salts also cause toner particles containing them to display lower fusing temperatures and improved paper adhesion indexes.
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(2008/06/13)

FLUOROCARBON DERIVATIVES OF NITROGEN. PART 19. SYNTHESIS AND MASS SPECTROMETRIC ANALYSIS OF SOME PYRIDINIUM (TETRAFLUORO-4-PYRIDYL)METHYLIDES
Nine new pyridinium methylides have been synthesised via SNAr displacement of the 4-fluorine from pentafluoropyridine with pyridinium phenacylide py+-C-(COPh)C5F4N-4> and a range of pyridium alkoxycarbonylmethylides
Banks, Ronald Eric,Flowers, William Thain,Khaffaf, Suad Najmaldin
p. 127 - 142
(2007/10/02)

Catalysis of ester aminolysis by divalent metal ions
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Propst III, Robert M.,Trzupek, Larry S.
p. 3233 - 3235
(2007/10/02)

Preparation of Tetrahydroindolizines from Pyridinuim and Isoquinolinium Ylides
Carbonyl- and nitrile-stabilised pyridinium and cyclic azonium methylides condense with chalcones to form tetrahydroindolizines and analogous fused pyrrolidines.The stereochemistry is illuminated by 13C and 1H n.m.r. spectroscopy.Several incorrect literature structures are rectified.
Katritzky, Alan R.,Grzeskowiak, Nicholas E.,Alvarez-Builla, Julio
p. 1180 - 1185
(2007/10/02)