- Imidazole oxime ester compound, preparation method, composition and use thereof (by machine translation)
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The invention relates to novel imidazole oxime ester compound, preparation method, composition and in photoinitiators, photosensitizers, the light absorbent, or sensitizers of the application. The invention imidazole oxime ester compound, at the same time with imidazole kind of light initiator (for example BCIM) and oxime mere initiator (for example 0 XE - 1) structural features. In one aspect, the compounds of the invention has improved the imidazole kind of light will produce sludge to the shortcoming of the initiator. On the other hand, compound of the present invention improved the thermal stability of the oxime [...] initiator problem not good, and increasing the operating convenience. (by machine translation)
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Paragraph 0039-0042
(2019/05/11)
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- Potential photoacid generators based on oxime sulfonates
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The bis-oxime of acenaphthenequinone and the mono-oxime of benzil have been sulfonated by reaction with 4-methylbenzenesulfonyl chloride and propylsulfonyl chloride. The four sulfonated oximes were characterised by X-ray single-crystal structure determinations. Some photochemical decompositions were studied using a 6-W 254-nm immersion well lamp in dichloromethane. The 4-methylbenzenesulfonate bis-oxime of acenaphthenequinone and the 4-methylbenzenesulfonate mono-oxime of benzil both give 4-methylbenzenesulfonic acid upon irradiation but not 4-methylbenzenesulfinic acid. Fragmentation pathways are discussed. The possible use of these compounds as photoacid generators in polymer resists and the role of secondary reactions to liberate acid is discussed.
- Plater, M. John,Harrison, William T. A.,Killah, Ross
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- Discovery of a series of ruthenium(II) derivatives with α-dicarbonylmonoxime as novel inhibitors of cancer cells invasion and metastasis
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A series of novel ruthenium(II)-cymene complexes (1–9) with substituted α-dicarbonylmonoximes of general formula [Ru(η6-cymene)(L)Cl] (L?=?N,O-chelating bidentate α-dicarbonylmonoxime derivatives) have been synthesized and characterized by elemental analysis, IR, 1H NMR, 13C NMR spectroscopies, and in three cases by single crystal X-ray diffraction analysis. The most effective compound 9 displays remarkable anti-invasion and anti-metastasis properties without apparent cytotoxicity toward three different human cancer cell lines (MCF-7, Hela and HepG2). Further protein level studies suggest that the anti-metastasis activity of the complexes may result from the increasing expression of E-cadherin and reducing expression of Vimentin.
- He, Yihui,Xue, Huiying,Zhang, Wendian,Wang, Li,Xiang, Guangya,Li, Lei,Shang, Xianmei
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- Green and highly selective protocol for the synthesis of oximes
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A green and efficient protocol has been developed for the synthesis of either exclusively a monoxime or exclusively a dioxime from a host of 1,2-dicarbonyl compounds on silica.
- Ghosh, Pranab,Subba, Raju
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p. 529 - 532
(2013/11/06)
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- Synthesis of oximes with NH2OH.HCl/DOWEX(R)50WX4 system
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The oximation of a variety of carbonyl compounds was efficiently carried out with DOWEX(R)50WX4/NH2OH·HCl system. The reactions were performed in ethanol to give Z-aldoximation isomers of aldehydes and E-oximaton of acetophenone derivatives in a perfect selectively. The oximation of compounds with two carbonyl groups was carried out selectively on one carbonyl moiety. Also, the oximation of aldehydes over ketones has been accomplished successfully by this system.
- Setamdideh, Davood,Khezri, Behrooz,Esmaeilzadeh, Seyran
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p. 1119 - 1124
(2012/10/30)
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- Optically active imidazoles derived from enantiomerically pure trans-1,2-diaminocyclohexane
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A new exploration of monoprotected derivatives of trans-1,2- diaminocyclohexane as a platform for the synthesis of enantiomerically pure imidazole derivatives is described. The primary amino group (-NH2), present in the mono-imine derivative of salicylic aldehyde (hemi-salen derivative) 5 was used for sequential reactions with formaldehyde and the corresponding α-(hydroxyimino)ketone. (S)-(-)-1-Phenylethylamine was also used as starting material for the preparation of new imidazole N-oxides 7c and 10a-c, bearing a chiral N-(1-phenylethyl)carboxamido function at C(4). Imidazole N-oxides 10a,b possessing either a Me or i-Pr group at N(1), respectively, follow the known sulfur-transfer pathway to afford the corresponding imidazole-2-thiones 13a,b. However, in the case of imidazole N-oxide 10c with a bulky adamantan-1-yl substituent at N(1), the attempted 'sulfur-transfer reaction' led to the deoxygenated imidazole derivative 14. Finally, the same reaction with 7c, which bears an electron-withdrawing N-(1-phenylethyl) carboxamide residue at C(4) of the imidazole ring, yielded a mixture of deoxygenated imidazole 16 and imidazole-2-thione 15c.
- Mloston, Grzegorz,Rygielska, Dorota,Jasinski, Marcin,Heimgartner, Heinz
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body text
p. 669 - 674
(2011/07/08)
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- Preparation and structure of optically active imidazolium tetrafluoroborates : In search of new chiral ionic liquids
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Enantiomerically pure (R)-l-(l-phenylethyl)imidazoles 4a,b can be prepared conveniently from α-(hydroxyimino)ketones 1, (R)-l-phenylethylamine and formaldehyde, followed by deoxygenation with Raney-Ni. Similarly, the reaction with (R,R)-trans-cyc-lohexane-l,2-diamine yields enantiomerically pure (R, R)-trans-1,1'-cyclohex-ane-l,2-diyl)imidazoles 4c,d. Alkylation of these imidazole derivatives with alkylbromides leads to the corresponding 3-alkylimidazolium bromides 6 and 8, respectively, which on treatment with sodium tetrafluoroborate are transformed into the corresponding tetrafluoroborates 7 and 9. Whereas some of the imidazolium salts 7 show properties of chiral ionic liquids, the bis-imidazolium tetrafluoroborates 9 are high-melting crystalline materials.
- Mloston,Mucha,Tarka,Urbaniak,Linden,Heimgartner
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experimental part
p. 1105 - 1114
(2010/03/01)
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- Phenylation reaction of α-acylnitromethanes to give 1,2-diketone monooximes: Involvement of carbon electrophile at the position a to the nitro group
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The generality and the effects of substituents on phenylation reactions of α-acylnitromethanes catalyzed by trifluoromethanesulfonic acid have been studied. α-Aroylnitromethanes afforded benzil monooximes in good yield. In the case of aliphatic α-acylnitromethane, a similar phenylation reaction proceeded, but the yield of the phenylated 1,2-dione monooxime was low. These phenylation reactions represent examples of the generation of carbocation electrophiles at the α-position of a nitro group. Georg Thieme Verlag Stuttgart - New York.
- Takamoto, Mikihiro,Kurouchi, Hiroaki,Otani, Yuko,Ohwada, Tomohiko
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scheme or table
p. 4129 - 4136
(2011/03/17)
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- Synthesis and selected transformations of 1H-imidazole 3-oxides derived from amino acid esters
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A series of new optically active 1H-imidazole 3-oxides 5 with a substituted acetate group at N(1) as the chiral unit were prepared by the reaction of α-(hydroxyimino) ketones, α-amino acid methyl esters, and formaldehyde. In an analogous reaction, ethyl 2
- Jasinski, Marcin,Mloston, Grzegorz,Linden, Anthony,Heimgartner, Heinz
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experimental part
p. 1916 - 1933
(2009/02/07)
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- An efficient tandem oxidative-protection reaction of benzylic alcohols to corresponding arylhydrazones and oximes
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A mild and efficient one-pot synthesis of hydrazones and oximes from the reaction of the oxidation product of benzyl alcohols and phenols by 3,6-bis(triphenylphosphonium)cyclohexene dichromate with phenylhydrazine, 2,4-dinitrophenylhydrazine, and hydroxylamine is described. Copyright Taylor & Francis Group, LLC.
- Badri, Rashid,Shushizadeh, Mohammad Reza
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p. 601 - 605
(2007/10/03)
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- Oxidative regeneration of carbonyl compounds from their oximes using in situ generated superoxide
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Superoxide ion, generated in situ by the phase transfer reaction of potassium superoxide and 18-crown-6, brings about an easy oxidative regeneration of a variety of carbonyl compounds from their oximes under significantly mild reaction conditions at room temperature.
- Singh,Pandey, Jyotsna,Singh, Manorama
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p. 2552 - 2555
(2007/10/03)
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- 1,2,4-triazine N-oxide and N,N′-dioxide derivatives: Studies as potential hypoxic cytotoxins and DNA binder
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1,2,4-Triazine N-oxide and N,N′-dioxide derivatives were synthesized in order to obtain compounds as potential selective hypoxic cell cytotoxins. All the compounds were tested for their cytotoxicity in oxia and hypoxia and some of them for their capacity to DNA-interaction in oxia. They proved to be less active in hypoxic conditions than the parent compound, tirapazamine (3-aminobenzo[1,2-e]1,2,4-triazine N1,N4-dioxide). However, derivatives 6, 9, and 10 developed significant affinity for DNA in oxic conditions. The electrochemical properties revealed that the lack of hypoxic - cytoxicity was clearly related with their poor bioreductive characteristics.
- Cerecetto,Gonzalez,Onetto,Risso,Saenz,Seoane,Bruno,Alarcon,Olea-Azar,Lopez de Cerain,Ezpeleta,Monge
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p. 328 - 337
(2007/10/03)
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- Deprotection of Ketoximes Using Bismuth(II) Nitrate Pentahydrate
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Ketoximes undergo facile deprotection in acetone-H2O (9:1) in the presence of 0.5 equivalents of Bi(NO3)*5H2O. Bismuth(III) nitrate is relatively non-toxic, insensitive to air and inexpensive. These features coupled with the use of a relatively non-toxic solvent system make this method an attractive alternative to existing routes for deprotection of ketoximes.
- Nattier, Bryce A.,Eash, Kyle J.,Mohan, Ram S.
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p. 1010 - 1012
(2007/10/03)
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- A new and general method for the synthesis of quinoxalines
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A new and general synthetic method for the preparation of 2,3-disubstituted quinoxalines is described. Treatment of ?-phenylenediamine with α-ketoaldoximes in ethanol affords 2,3-disubstituted quinoxalines in one-step reaction.
- Tajbakhsh,Bakooie,Ghassemzadeh,Beheshtiha,Heravi
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p. 1232 - 1233
(2007/10/03)
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- A rapid and convenient synthesis of oximes in dry media under microwave irradiation
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In a novel method, the reaction of hydroxylamine hydrochloride with a number of aldehydes and ketones under microwave irradiation and solventless 'dry' condition gave oximes in excellent yield.
- Hajipour, Abdol Reza,Mallakpour, Shadpour E.,Imanzadeh, Gholamhasan
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p. 228 - 229
(2007/10/03)
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- A New General Method for the Synthesis of 4-Hydroxylated 3-Aryltetrahydroisoquinolines
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3-Aryl-4-hydroxytetrahydroisoquinolines have been prepared from deoxybenzoins.The nitrosation of the latter derivatives has been improved and the catalytic reduction of the obtained oximinoketones has been carried out with the help of ultrasounds.Heterocyclization to the isoquinoline moiety occurred on the unprotected 1,2-aminoalcohol to give stereoselectively the corresponding hydroxylated heterocycle with good yield.
- SanMartin, Raul,Olivera, Roberto,Marigorta, Eduardo Martinez de,Dominguez, Esther
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p. 5361 - 5368
(2007/10/02)
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- Ozonolysis Of Substituted Isoxazoles
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The ozonolysis of substituted isoxazoles was investigated.The ozonolysis rates and the products were dependent on the site of the substituent group on isoxazole ring.The reaction mechanism of the ozonolysis of isoxazoles was also proposed.
- Kashima, Choji,Takahashi, Katsumi,Hosomi, Akira
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p. 1075 - 1082
(2007/10/02)
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- ORGANIC SYNTHESIS USING ORGANOSULFUR-NITRITES AND -NITRATES
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Thionitrites or thionitrates have been considered to be unstable.However, bulky groups' thio-NOn such as t-butylthio-nitrites and -nitrates have been readily synthesized and found to be stable enough for the use of the useful organic syntheses as an excellent nitrosation and diazotization reagents under mild conditions.Direct conversion of amines to the corresponding halides in the presence of copper halides (II), fluorination of heterocyclic amines in the presence of sodium tetrafluoroborate, α- oximation of methylene groups in ketones, facile cleavage of C=N bond to ketones, and desulfurization of thioacetals and thioketals, and other useful organic syntheses are described.
- Kim, Yong Hae
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p. 249 - 260
(2007/10/02)
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- Hydroxynitrilium ions as intermediates in the reaction of nitroderivatives with aromatics
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In acids reaction of ethyl nitroacetate 1 and of a nitroacetophenone 14 with aromatics yields E oximes 2 and 15, respectively, addition occurring on the corresponding hydroxynitrilium ion.
- Coustard, Jean-Marie,Jacquesy, Jean Claude,Violeau, Bruno
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p. 3075 - 3078
(2007/10/02)
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- Friedel-Crafts-type reactions involving di- and tricationic species. Onium-allyl dications and O,O-diprotonated aci-nitro species bearing a protonated carbonyl group
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Stable carbocations do not react with nonactivated benzenes. For example, acetophenone does not react with benzene in the presence of trifluoromethanesulfonic acid (TFSA), while trifluoroacetophenone does do so under acidic conditions owing to activation of the electrophilicity of the hydroxycarbenium cation by the trifluoromethyl group. This and other studies suggest that an electron-withdrawing substituent on the cationic center increases the reactivity toward benzenes. In this paper, involvement of multiply positively charged (dicationic and tricationic) species, which have sufficient electrophilicity toward benzene, is demonstrated in the acid-catalyzed reactions of cinnamaldehyde and its derivatives and also in the acid-catalyzed reactions of nitromethanes. The species formed from cinnamaldehyde, cinnamaldimine, cinnamaldoxime, and their derivatives in TFSA or TFSA-SbF5 have an adequate reactivity toward benzene. O-Protonated cinnamaldehyde and its derivatives, N-protonated cinnamaldimine, and N,N-dimethylcinnamaldiminium salt do not react with benzene. Since a strong acid catalyst is required for the reactions, participation of doubly protonated species, onium-allyl dications, is proposed. Ab initio calculations of (1) the donor-acceptor interaction energies of a neutral donor (such as water and ammonia) and a doubly charged allyl dication and (2) proton affinities demonstrated that the ammonium-allyl dication is more stable than the oxonium-allyl dication, in accordance with the experimental observation. Nitronic acids also react with benzene at the ipso position with respect to the nitro group to give the phenylated oximes in the presence of TFSA. The reaction with benzene is not catalyzed by trifluoroacetic acid, which is sufficiently acidic to monoprotonate a nitronic acid to the protonated aci-nitro form. The reaction requires a stronger acid, trifluoromethanesulfonic acid, suggesting intervention of the dication formed by O,O-diprotonation of acinitroalkanes rather than the monoprotonated aci-nitroalkane. As a result of further study on the phenylation reactions, we found a facile phenylation reaction of nitromethanes substituted with an electron-withdrawing group, catalyzed by TFSA, to give phenylated α-carbonyloximes in high yields. A triply positively charged cation, an O,O-diprotonated aci-nitro species bearing a protonated ethoxycarbonyl group, which can react with nonactivated benzene, is proposed to be an intermediate in this reaction.
- Ohwada, Tomohiko,Yamagata, Naoko,Shudo, Koichi
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p. 1364 - 1373
(2007/10/02)
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- FACILE DIRECT α-OXIMATION OF KETONES USING t-BUTYL THIONITRATE
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Various ketones containing methylene groups at α-position were found to react with t-butyl thionitrate at 0 deg C in tetrahydrofuran to give the corresponding α-oximino-ketones in excellent yield.
- Kim, Yong Hae,Park, Young Jun,Kim, Kweon
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p. 2833 - 2836
(2007/10/02)
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