cas 2299-73-2, 4-METHOXYBENZALDEHYDE AZINE

Articles about 2299-73-2Total 58 be found

Article title
Article abstract
Author
Journal number and time
Download

Ruthenium(ii)-catalysed 1,2-selective hydroboration of aldazines
Herein, an efficient and simple catalytic method for the selective and partial reduction of aldazines using ruthenium catalyst [Ru(p-cymene)Cl2]2 (1) has been accomplished. Under mild conditions, aldazines undergo the addition of pinacolborane in the presence of a ruthenium catalyst, which delivered N-boryl-N-benzyl hydrazone products. Notably, the reaction is highly selective, and results in exclusive mono-hydroboration and desymmetrization of symmetrical aldazines. Mechanistic studies indicate the involvement of in situ formed intermediate [{(η6-p-cymene)RuCl}2(μ-H-μ-Cl)] (1a) in this selective hydroboration.
Gunanathan, Chidambaram,Pradhan, Subham,Thiyagarajan, Subramanian
supporting information
p. 7147 - 7151
(2021/08/30)

Synthesis and antimicrobial activity of some new coumarin and dicoumarol derivatives
PTC reaction of coumarin derivative 1 with alkyl halides afforded C4 oxygen alkylation products 2a-d in appreciative yield, whereas with phenyl isothiocyanate gives the C3 addition product 4; also, one-pot three-component PTC reactio
El-Metwally, Souad A.,Regal, Mohsen K. A.,Shaban, Safa S.
(2020/01/22)

Synthesis and Antimicrobial Activity of Some New Coumarin and Dicoumarol Derivatives
Abstract: Phase transfer catalysis reaction of 4-hydroxy-6-methyl-2H-chromen-2-one with alkyl halides afforded C4 oxygen alkylation products of 2H-chromen-2-one derivatives in appreciative yield, whereas with phenyl isothiocyanate gives the C3 addition product of 4-hydroxy-6-methyl-2-oxo-N-phenyl-2H-chromene-3-carbothioamide, also one pot three component phase transfer reaction was investigated. Treatment of 4-hydroxy-6-methyl-2H-chromen-2-one with aromatic aldehydes in different molar ratios gives 3?arylidine and the dicoumarol derivatives. However pyrano chromene and pyrano pyridine were obtained by reaction of arylidine with ethyl acetoacetate through Michael cycloaddition reaction. The stability of pyrone ring in 3-arylidine and dicoumarol towards different nucleophilic reagents under reflux and/or fusion conditions has been studied by the action of, hydrazine hydrate, ammonium acetate, methyl amine and p-toluidine afforded compounds 1,2-bis(benzo[d][1,3]dioxol-5-ylmethylene)hydrazine, 1,2-bis(4-methoxybenzylidene)hydrazine and 2,6-bis((2,6-dihydroxy-3-methylphenyl)(hydroxy)methylene)-1-(4-methoxyphenyl)-4-(p-tolyl) piperidine-3,5-dione derivatives. The antimicrobial activity of some synthesized compounds has been investigated.
El-Metwally, S. A.,Regal, M. K. A.,Shaban, S. S.
p. 438 - 447
(2020/06/30)

Glucose:urea:NH4Cl low melting mixture for the synthesis of symmetric azines
Alternate reaction media have become very important due to the problems created by the highly volatile nature of the solvents. The deep eutectic mixture is a kind of an alternate reaction medium which has emerged in recent years. Low melting mixtures were introduced by making the deep eutectic mixture more cost-effective and renewable by introducing carbohydrates into it. The properties of low melting mixtures include easiness to prepare, usage of low-cost components, biodegradability, solubility in water, easy separation from organic compounds, etc. The low melting mixtures such as glucose:urea:NH4Cl, glucose:ChCl, glucose:urea:ChCl, glycerol:urea:NH4Cl, and ethylene glycol:urea:NH4Cl were used in different ratios for the reactions. The properties such as viscosity, density, acidity, glass transition temperature, and thermal stability were studied. An unusual method for the synthesis of symmetrical azines is introduced wherein benzaldehyde and hydroxylamine are reacted in the presence of glucose:urea:NH4Cl. The method of synthesis needs only less reaction time, temperature and the product was easily separated. The products were confirmed using GC-MS and NMR techniques. The recyclability of glucose:urea:NH4Cl was studied.
Theresa, Letcy V.,Shaibuna,Sreekumar
p. 3148 - 3160
(2019/09/03)

Unprecedented synthesis of symmetrical azines from alcohols and hydrazine hydrate using nickel based NNN-pincer catalyst: An experimental and computational study
Azines are having widespread applications in both industry as well as synthetic chemistry. Thus new catalytic synthetic protocols are desirable as they are greener alternatives than traditional methods of synthesis. Thus, herein a novel earth abundant nickel based NNN-pincer catalyst Ni(BPEA)(Cl2) is synthesized for the first time for the direct transformation of alcohols and hydrazine hydrate into symmetrical azines. This catalytic reaction is accompanied by dehydrogenative coupling of alcohols and hydrazine hydrate and is carried out in presence of a base. Theoretical calculations supported by experimental evidence have been performed for understanding the mechanistic insights of the reaction.
Shiekh, Bilal Ahmad,Kaur, Damanjit,Godara, Sachin Kumar
p. 19 - 23
(2019/03/02)

Dihydrazone compound high in affinity with Abeta protein and Tau protein, derivative thereof, and applications of dihydrazone compound and derivative
The invention provides a dihydrazone compound high in affinity with Abeta protein and Tau protein, a derivative thereof, and applications of the dihydrazone compound and the derivative. The structureof the dihydrazone compound is represented by formula I. The dihydrazone compound can be directly taken as a fluorescence probe used for detecting neurofibrillary tangles in vivo or in tissue samples;when the dihydrazone compound is adopted in nuclear medicine imaging, appropriate radioisotopes are needed for labeling. The dihydrazone compound is especially suitable to be used for diagnosis of neurodegenerative diseases, and diagnosis of patients with diseases with Abeta plaques including Alzheimer's disease.
-
Paragraph 0029-0031; 0047-0049

(2019/05/15)

Unusual synthesis of azines and their oxidative degradation to carboxylic acid using iodobenzene diacetate
Reaction of 3-hydrazonobutan-2-one oxime with aromatic aldehydes resulted in the formation of 1,2-bis(arylidene)hydrazine commonly referred as azine as an unexpected product, instead of expected product 3-(aryl)methylenehydrazonobutan-2-one oxime, which were subsequently oxidized to corresponding aromatic acids with an ecofriendly oxidizing agent iodobenzene diacetate. Azines and carboxylic acids were characterized by IR and NMR (1H, 13C, HMBC, and HMQC) studies.
Sumran, Garima,Aggarwal, Ranjana,Hooda, Mona,Sanz, Dionisia,Claramunt, Rosa M.
supporting information
p. 439 - 446
(2018/02/06)

Li+-Induced fluorescent metallogel: A case of ESIPT-CHEF and ICT phenomenon
A fluorescent metallogel (1percent w/v) has been synthesized from non-fluorescent ingredients viz. the smallest possible low molecular weight aromatic symmetrical ligand H2SA (1) and LiOH in a chloroform and methanol mixture. The chelation of Li+ is not only responsible for the inhibition of excited state intramolecular proton transfer (ESIPT) or the origin of fluorescence through chelation enhanced fluorescence (CHEF) in 1, but also for aggregation leading to gelation. The metallogel obtained from 1/Li+ reveals a fibrous morphology while 1 with other, bigger size, alkali metal ions like Na+/K+/Cs+ demonstrates the growth of crystals with different shapes. The effect of the size of the alkali metal ion over gel formation is well explored by FTIR, UV-vis, fluorescence, average lifetime measurements, SEM and PXRD. The metallogel shows multi-stimuli responsive behaviour towards thermal and mechanical stress as well as reswelling properties. The regioisomer H2PBA (2) also shows emission upon treatment with LiOH due to the presence of intramolecular charge transfer (ICT), this is well established by various experiments. The mechanism of gel formation is well established by FTIR, 1H NMR, UV-vis, fluorescence, lifetime measurements, SEM and single crystal and powder XRD instrumental techniques. The involvement of various phenomena in gel formation has been further supported by other synthesized model compounds viz. H2MBA (3), PMO (4), H2SEA (5) and H2SPA (6). True gel phase material is proved by detailed rheological experiments.
Dixit, Manish Kumar,Dubey, Mrigendra
p. 23762 - 23772
(2018/09/29)

Synthesis and Properties of New 4-Oxo-4,5-dihydro-1,3-oxazolium Perchlorates
D-Pantoic acid amide obtained by treatment of D-(–)-pantolactone with ammonia reacted with acetic anhydride in the presence of perchloric acid to give 5-[2-(acetoxy)-1,1-dimethylethyl]-2-methyl-4-oxo- 4,5-dihydro-1,3-oxazolium perchlorate. Reaction of the
Lukina, D. Yu.,Strelkov,Dyadyuchenko,Chigorina,Dotsenko,Kosulina
p. 2504 - 2512
(2019/04/03)

Mononuclear half-sandwich iridium and rhodium complexes through C?H activation: Synthesis, characterization and catalytic activity
A series of mononuclear half-sandwich cyclometalated group 9 (Ir and Rh) metal complexes were synthesized in good yields through metal-mediated C?H bond activation. These air-stable C, N-chelate mode complexes have similar solid state structures. Both experimental results and DFT calculations confirmed that no binuclear complexes were generated in this reaction. The iridium complex 3a exhibited good catalytic activity for the reduction of both electron-rich and electron-poor aryl imines with low catalyst loading in the presence of formic acid/triethylamine (F/T) azeotropic mixture. All complexes were fully characterized by elemental analysis and IR and NMR spectroscopies. The structures of 1a, 1b, 2a, 3a and 4b (see chemical structure formula in Scheme 1 and Scheme 2) were further confirmed by single-crystal X-ray analysis.
Yao, Zi-Jian,Li, Kuan,Li, Peng,Deng, Wei
p. 208 - 216
(2017/07/05)

C[sbnd]N bond formation in alicyclic and heterocyclic compounds by amine-modified nanoclay
In the current protocol, amine functionalized montmorillonite K10 nanoclay (NH2-MMT) was applied to catalyze the formation of C[sbnd]N bonds in the synthesis of azines and 2-aminothiazoles at room temperature. In comparison with the current methods of C[sbnd]N bond formation, this approach displays specific advantages include atom economy, clean conversion, design for energy efficiency, the use of nontoxic and heterogeneous catalyst, higher purity and yields, safer solvent and reagents for this organic transformation.
Zarnegar, Zohre,Alizadeh, Roghayeh,Ahmadzadeh, Majid,Safari, Javad
p. 58 - 65
(2017/05/12)

Efficient and practical method for the synthesis of hydrophobic azines as liquid crystalline materials
A series of hydrophobic symmetrical azines: 1,2-bis[4-(n-alkoxy)benzylidene]hydrazine (where, n-alkoxy: O(CH2)nH, n = 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 12, 16, or 18) have been prepared following an efficient and practical method. These compounds have been synthesized via the condensation reaction of hydrazine hydrate and appropriately 4-(n-alkoxy) benzaldehydes in acidic medium under ambient conditions. The prepared organic compounds have been characterized and their structures were elucidated depending upon micro-elemental analysis and spectral data (IR, UV-Vis, 1HNMR, 13C{1H}NMR, 2D 1H-1H-cozy, 2D 1H-13C-HSQC, and mass spectra). Liquid crystalline behavior of the prepared compounds was studied using polarized light optical microscopy and differential scanning calorimetry techniques. This study revealed that all the compounds displayed enantiotropic liquid crystal properties, exhibiting smectic and nematic mesophases.
Hammood, Ali Jasim,Kased, Ahmed Fadhel H.,Al-Karawi, Ahmed Jasim M.,Raseen, Sameem R.,Tomi, Ivan Hameed R.,Omar Ali, Al-Ameen Bariz
p. 114 - 129
(2017/07/04)

A Copper-Benzotriazole-Based Coordination Polymer Catalyzes the Efficient One-Pot Synthesis of (N′-Substituted)-hydrazo-4-aryl-1,4-dihydropyridines from Azines
A series of new (N′-substituted)-hydrazo-4-aryl-1,4-dihydropyridines was successfully synthesized via a facile one-pot catalytic pathway utilizing azines and propiolate esters as starting materials and a one-dimensional copper benzotriazole-based coordination polymer as catalyst. In the absence of catalyst, the corresponding 5-substituted 4,5-dihydropyrazoles were formed in moderate to high yields. Fine-tuning of the catalysts allowed us to gain more insights regarding the plausible reaction mechanism. (Figure presented.).
Kallitsakis, Michael,Loukopoulos, Edward,Abdul-Sada, Alaa,Tizzard, Graham J.,Coles, Simon J.,Kostakis, George E.,Lykakis, Ioannis N.
supporting information
p. 138 - 145
(2017/01/14)

Synthesis of New symmetrical N,N'-diacylhydrazines and 2-(1,2,3-triazol-4-yl)-1,3,4-oxadiazoles
Background: The aim of the current research was to synthesize novel symmetrical N,N'-diacylhydrazines through oxidation of acid carbohydrazide using ethyl 2-cyano-3-methoxyacrylate or 2-(methoxymethylene)malononitrile as organo-catalyst. Also, novel 2-(1,
Abdel-Wahab, Bakr F.,Alotaibi, Mohammad Hayal,El-Hiti, Gamal A.
p. 591 - 596
(2017/09/28)

Azines from one-pot reaction of thiosemicarbazones
Thermolysis and/or microwave irradiation of thiosemicarbazones gave the corresponding isothiocyanates, which on addition of either activated nitriles or aldehydes furnished various types of azines. The mechanism was discussed. The structures of products were proved by MS, IR, NMR, and elemental analyses (Image presented).
Aly, Ashraf A.,Hassan, Alaa A.,Brown, Alan B.,Ibrahim, Mahmoud A. A.,Abdal-Latif, El-Shimaa S. M.
p. 11 - 17
(2018/12/14)

Tungsten hexachloride nanoparticles loaded on montmorillonite K-10: a novel solid acid catalyst in the synthesis of symmetrical and unsymmetrical azines
In the present investigation, we have developed a novel technique to prepare azines using nano-WCl6 loaded on Montmorillonite K10 clay as a highly active catalyst. A variety of aldehydes and ketones were efficiently converted to the corresponding azines using catalytic amounts of nanosized WCl6/Mont. K10 under mild conditions. The nanostructures of WCl6 loaded on Mont. K10 as solid acid catalyst have been prepared by solid dispersion method. The advantages of this catalyst are rapid completion of the reactions, simplicity of performance, lack of pollution and mild and green reaction conditions. The morphologies, structure, and chemical components of parent and modified clay were successfully characterized using SEM, FT-IR, CV, XRD and EDX measurements.
Safari, Javad,Gandomi-Ravandi, Soheila,Shariat, Saeedeh
p. 1499 - 1507
(2016/07/06)

Nitrogen activation and conversion method promoted by divalent rare earth iodine compound
The invention belongs to the technical field of organic chemical synthesis, and particularly relates to a method for activating and converting nitrogen through a divalent rare earth compound. A divalent rare earth diodide is used as a reducing agent, a solvent is added in, the mixture reacts with nitrogen, then a hydrogen source is added in, and then the mixture reacts with an aldehyde or ketone compound to obtain an azine or pyridazine compound. According to the method, the nitrogen is activated and converted into the organic compound containing nitrogen on the mild condition. Compared with a classical ammonia synthesis path, strict reaction conditions such as high temperature, high pressure and ammonia oxidation are avoided, and the method is of great significance in developing the new technology of nitrogen molecule activation and broadening the application range of rare earth metal in organic synthesis.
-
Paragraph 0023; 0024

(2016/12/01)

Direct synthesis of symmetrical azines from alcohols and hydrazine catalyzed by a ruthenium pincer complex: Effect of hydrogen bonding
Azines (2,3-diazabuta-1,3-dienes) are a widely used class of compounds with conjugated CN double bonds. Herein, we present a direct synthesis of azines from alcohols and hydrazine hydrate. The reaction, catalyzed by a ruthenium pincer complex, evolves dihydrogen and can be run in a base-free version The deh dro enative cou lin of benz lic and aliphatic alcohols led to good conversions and yields. Spectroscopic evidence for a hydrazine-coordinated dearomatized ruthenium pincer complex was obtained. Isolation of a supramolecular crystalline compound provided evidence for the important role of hydrogen bonding networks under the reaction conditions.
Bauer, Jonathan O.,Leitus, Gregory,Ben-David, Yehoshoa,Milstein, David
p. 8415 - 8419
(2018/05/23)

Metal-Free Synthesis of 1,3,4-Oxadiazoles from N′-(Arylmethyl)hydrazides or 1-(Arylmethyl)-2-(arylmethylene)hydrazines
An efficient and versatile metal-free synthesis of 1,3,4-oxadiazoles from N′-(arylmethyl)hydrazides or 1-(arylmethyl)-2-(arylmethylene)hydrazines through oxidative dehydrogenation is reported. A range of 2,5-disubstituted 1,3,4-oxadiazoles were prepared by treating N′-(arylmethyl)hydrazides with (diacetoxyiodo)benzene in acetonitrile or by treating 1-(arylmethyl)-2-(arylmethylene)hydrazines with [bis(trifluoroacetoxy)iodo]benzene in methyl tert-butyl ether. Aldehyde N-acylhydrazones and aldazines were initially generated in situ as intermediates.
Shang, Zhenhua,Chu, Qianqian,Tan, Sheng
p. 1032 - 1040
(2015/03/30)

An efficient synthesis of perhydro[1,2,4]triazolo[1,2-a][1,2,4]triazole-1,5-dithiones catalyzed by TiO2-functionalized nano-Fe3O4 encapsulated-silica particles as a reusable magnetic nanocatalyst
Immobilization of a nano-TiO2 catalyst on the surface of a magnetic SiO2 support was performed through the reaction of a Fe3O4@SiO2 composite with Ti(OC4H9)4via a simple process. The Fe3O4@SiO2-TiO2 nanocomposite was characterized using scanning electron microscopy (SEM), transmission electron microscopy (TEM), energy dispersive X-ray spectroscopy (EDS), X-ray diffraction (XRD), Fourier transform infrared spectra (FTIR), and a vibrating sample magnetometer (VSM). The Fe3O4@SiO2-TiO2 nanocomposite has been found to be an efficient catalyst for the synthesis of perhydro[1,2,4]triazolo[1,2-a][1,2,4]triazole-1,5-dithiones from the condensation of various aldazines and potassium thiocyanate in acetonitrile solvent at room temperature. It has been found that the nanocatalyst was recycled for up to 6 cycles with minimal loss in catalytic activity. The purpose of this research was to provide an easy method for the synthesis of perhydrotriazolotriazole derivatives by a robust and magnetically recoverable catalyst.
Safari, Javad,Javadian, Leila
p. 104973 - 104980
(2015/12/26)

Hydrolysis and hydrazinolysis of isatin-based ald-and ketazines
The hydrolysis of isatin aldazine 4a-d afforded the unexpected 3,3'-(hydrazine-1,2-diylidene)bis(indolin-2-one) (5) and 1,2-di(arylidene)hydrazines 6a-d through dual hydrolysis of 4a-d. A mechanism to explain the formation of 5 and 6a-d was proposed. In addition, the hydrazinolysis of 4a-d yielded 3-hydrazonoindolin-2-one (2) and 1,2-di(arylidene)hydrazines 6a-d instead of hydrazones 17a-d, while hydrazinolysis of isatin ketazine 5 gave the expected 3-hydrazonoindolin-2-one (2). These results indicated the ability of the title compounds for unusual hydrolysis and hydrazinolysis reactions.
Ibrahim, Hany S.,Abdelhadi, Soha R.,Abdel-Aziz, Hatem A.
(2015/05/27)

An expeditious synthetic approach towards the synthesis of Bis-Schiff bases (aldazines) using ultrasound
Aldazines (Bis-Schiff bases) 1-24 were synthesized using aromatic aldehydes (heterocyclic and benzaldehydes) and hydrazine hydrate under reflux using conventional heating and/or via ultrasound irradiation using BiCl3 as catalyst. Ultrasonication conditions with cat. BiCl3 proved to be an effective, environmentally friendly synthetic procedure. This methodology is robust in the presence of electron donating and electron withdrawing groups affording desired products with high yields (>95%) in just a couple of minutes vs. hours using conventional heating.
Khan, Khalid M.,Jamil, Waqas,Ambreen, Nida,Taha, Muhammad,Perveen, Shahnaz,Morales, Guillermo A.
p. 1200 - 1205
(2014/02/14)

Monohydrocyanation of symmetrical azines using potassium hexacyanoferrate(II) as an environmentally friendly cyanide source
The monohydrocyanation of symmetrical azines to synthesize α-hydrazinonitriles using potassium hexacyanoferrate(II) as cyanide source and benzoyl chloride as a promoter under catalyst-free conditions is described. The advantages of this protocol are the environmentally friendly cyanide source, high yield, and simple work-up procedure. Georg Thieme Verlag Stuttgart New York.
Hu, Xiaochun,Li, Hongbo,Yang, Jingya,Li, Zheng
supporting information
p. 1786 - 1790
(2014/08/05)

Anomalous reaction of hydrazine hydrate with 5-arylidene barbiturates: Formation of benzalazines
Reaction of 5-arylidene barbiturates (3a-i) with hydrazine hydrate resulted in the unusual formation of novel benzalazines (5a-i) in 70-90% yield rather than the expected pyrazole fused pyrimidines.
Goudgaon,Upendar Reddy, Ch.,Patil, Sharanabasappa,Sheshikant
p. 277 - 282
(2019/01/21)

Microwave-assisted synthesis of 1-hydrazinophosphonates via the reaction of aldazines with dialkyl phosphite
A simple, efficient, and novel method has been developed for the synthesis of 1-hydrazinophosphonic acids from aldazines. As described below, treatment of aldazines with diethyl phosphite gives the corresponding 1-hydrazinophosphonic acids in good yields. The reaction proceeds under microwave irradiation at 110°C and neutral condition without any additives such as base, acid, or catalyst. This method is easy, rapid, and gives good yields for the 1-hydrazinophosphonic acids.
Kaboudin, Babak,Alipour, Soheil
experimental part
p. 304 - 308
(2012/07/27)

Features of the reactions of β-Aryl(heteryl)-α-nitroacrylates with N,N-, N,O-, and N,S-Binucleophiles
The reactions of β-aryl(heteryl)-α-nitroacrylates with N,N-, N,O-, and N,S-binucleophiles proceed regiospecifically through the initial formation of the AdN products, among which only the product from oaminothiophenol was isolated. The conditions of converting the S-adducts into 2-aryl(heteryl)benzothiazole were found. The N-adducts formed in the reaction with hydrazine, o-phenylenediamine, and o-aminophenol undergo immediately the spontaneous transformation into the linear (azine, azomethine) or heterocyclic (benzimidazole) structures. Pleiades Publishing, Ltd., 2012.
Baichurina,Baichurin,Filippenko,Aboskalova,Berestovitskaya
p. 1400 - 1408
(2013/01/15)

Facile method for the conversion of semicarbazones/thiosemicarbazones into azines (Under Microwave Irradiation) and oxadiazoles (By Grinding)
In an effective transformation, semicarbazones/thiosemicarbazones are smoothly converted into azines under microwave irradition. Oxadiazoles are also obtained from semicarbazones by reaction with bromine generated in situ via a grinding reaction in the solid phase. Taylor &Francis Group, LLC.
Chattopadhyay, Gautam,Ray, Partha Sinha
p. 2607 - 2614
(2011/08/07)

Synthesis of functionalized diaryl alkancs from azines
Substituted diaryl alkanes arc synthesized from bcnzalazines and acctophenone/propiophenone azines via Friedel Craft's reaction with substituted mono- and poly-nuclear aromatic hydrocarbons. Diaryl methanes/ethanes and propanes are obtained by reaction with benzalazine, N,N'-bis (I-phenyl) azine and N, N'-bis (I-propyl) azine, respectively.
Manih, Rudolf M.,Myrboh, Bekington
experimental part
p. 146 - 151
(2009/12/01)

Selective and convenient protection of aldehydes as azines under solvent-free conditions
Aldehydes can be easily protected as azines in the presence of hydrazine monohydrochloride and ferric chloride under solvent-free conditions. The major advantages of this method are: operational simplicity, ready availability, selectivity, general applicability, mild reaction conditions with low cost of the reactants, short reaction times and excellent yields.
Eshghi, Hossein,Hosseini, Mosayyeb
experimental part
p. 636 - 638
(2009/05/11)

Synthesis of some new pyrazoloquinazolinone and quinazolinone derivatives
The benzoxazinone derivative 2-(6,8-dibromo-4-oxo-4H-benzo[d]-1,3-oxazin-2- yl)-3-(4-methoxy-phenyl)acrylonitrile (1) has been used as a starting material for preparation of the hitherto unknown pyrazoloquinazolinone and quinazolinone derivatives. Under d
El-Khamry,Shiba,Shalaby,Abd Alaha
p. 1189 - 1193
(2007/10/03)

The catalytic olefination reaction of aldehydes and ketones with CBr 3CF3
The new approach of catalytic olefination reaction (COR) has been used to convert aromatic and aliphatic aldehydes and ketones to 2-bromo-3,3,3- trifluoroprop-1-enes by the treatment of corresponding hydrazones with CBr 3CF3 under copper(I) catalysis conditions. The reaction proceeds stereoselectively, the target alkenes were obtained in good yields.
Nenajdenko, Valentine G.,Varseev, Georgy N.,Shastin, Alexey V.,Balenkova, Elisabeth S.
p. 907 - 913
(2007/10/03)

Orthoamide, LX [1]. N,N,N',N'-Tetraformylhydrazine- a Formylation Agent for Aromatic Compounds of Wide Scope
The reagent system formed from N,N,N',N'-tetraformylhydrazine (3) and aluminum chloride allows the formylation of aromatic compounds. The scope of the method is comparable with the Olah formylation and the Gross-Rieche procedure, since benzene and fluorobenzene can be formylated. Two formyl groups are transferred from 3 to the aromatic nuclei when a molar ratio 4:1:4 (aluminum chloride/3/aromatic compound) is chosen.
Kantlehner, Willi,Haug, Erwin,Scherr, Oliver,Stoyanov, Edmont V.,Mezger, Jochen,Ziegler, Georg
p. 355 - 365
(2007/10/03)

Reaction of CBrF2-CBrF2 with hydrazones of aromatic aldehydes. Novel efficient synthesis of fluorocontaining alkanes, alkenes and alkynes
An olefination of hydrazones of aromatic aldehydes by CBrF2-CBrF2 under copper catalysis was investigated. In situ prepared aldehydes hydrazones were converted to (3-bromo-2,2,3,3-tetrafluoropropyl)arenes by reaction with CBrF2-CBrF2 in the presence of CuCl. Subsequent elimination of HF by sodium hydroxide resulted in stereospecific formation of fluorocontaining alkenes. Elimination proceeds stereoselectively, only Z -isomers of alkenes are formed. Elimination of two molecules of HF from (3-bromo-2,2,3,3-tetrafluoropropyl)arenes by treatment with potassium tert -butoxide leads to formation of (bromodifluoromethyl)alkynes. As a result a simple and efficient transformation of aromatic aldehydes to range of various fluorinated alkanes, alkenes and alkynes was elaborated.
Nenajdenko, Valentine G.,Varseev, Georgy N.,Korotchenko, Vasily N.,Shastin, Alexey V.,Balenkova, Elisabeth S.
p. 1339 - 1345
(2007/10/03)

A novel direct synthesis of (2,2-difluorovinyl)benzenes from aromatic aldehydes
A novel catalytic approach to (2,2-difluorovinyl)benzenes has been developed. It was found that hydrazones of aromatic aldehydes generated in situ could be converted to the corresponding (2,2-difluorovinyl)benzenes by catalytic olefination reaction (COR) with dibromodifluoromethane in the presence of CuCl.
Nenajdenko, Valentine G.,Varseev, Georgy N.,Korotchenko, Vasily N.,Shastin, Alexey V.,Balenkova, Elisabeth S.
p. 115 - 118
(2007/10/03)

A novel approach to 2-chloro-2-fluorostyrenes
A new general catalytic olefination reaction (COR) of aromatic and heteroaromatic aldehydes and ketones was applied to synthesise 2-chloro-2-fluorostyrenes. The two-stage procedure includes the transformation of carbonyl compounds into hydrazones followed by treatment with CFCl3 mediated by copper catalysis. Trichlorofluoromethane was used as a chlorofluoromethylene transfer reagent. The reaction proceeds stereoselectively and the target alkenes were obtained in high yield. A proposed mechanism for the reaction is discussed. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.
Nenajdenko, Valentine G.,Shastin, Alexey V.,Korotchenko, Vasily N.,Varseev, Georgy N.,Balenkova, Elisabeth S.
p. 302 - 308
(2007/10/03)

Catalytic olefination of carbonyl compounds. Effect of the structure of the carbonyl compound on the reaction
The mechanism of the novel reaction of catalytic olefination of carbonyl compounds was studied. The reaction involves the transformation of hydrazones of aromatic aldehydes and ketones into the corresponding dichloroalkenes and symmetrical azines by the treatment with carbon tetrachloride in the presence of CuCl as a catalyst. The stability of intermediate diazoalkanes is the main factor determining the direction of the reaction. In the case of sufficiently stable diazoalkanes, other products can be formed under the reaction conditions along with the products of catalytic olefination.
Korotchenko,Shastin,Nenaidenko,Balenkova
p. 492 - 497
(2007/10/03)

A convenient synthesis of azines under solvent-free conditions using microwave irradiation
In an extremely fast method the reaction of hydrazine sulfate with a number of aldehydes and ketones, is accelerated by microwave irradiation under solvent free conditions in the presence of CH2CO2Na/CaCl2 to afford high yields of relevant azines.
Khouzani-Loghmani, Hossein,Sadeghi, Majid M. M.,Safari, Javad,Abdorrezaie, Mohammad S.,Jafarpisheh, Masood
p. 80 - 81
(2007/10/03)

One-pot oxidation of azomethine compounds into arenecarboxylic acids
Aromatic azomethine compounds, such as aldazines 1, aldoximes 7 and tosylhydrazones 8 oxidized with 30% hydrogen peroxide in the presence of poly(bis-1,2-phenylene) diselenide (6) as catalyst produce arenecarboxylic acids 2 mostly in high to excellent yields. The presented one-pot procedure has a synthetic value.
Giurg,Said,Syper,Mlochowski
p. 3151 - 3159
(2007/10/03)

A novel approach to fluoro-containing alkenes
A new and general one-pot transformation of aromatic aldehydes to fluorinated olefins containing -CH=C(Cl)CF3 or -CH=C(F)CClF2 moieties is described. Freons CCl3CF3 and CCl2FCClF2 were used as trifluoromethyl and difluoromethyl C2-building blocks respectively. A proposed mechanism for the reaction is discussed.
Korotchenko, Vasily N,Shastin, Alexey V,Nenajdenko, Valentine G,Balenkova, Elisabeth S
p. 7519 - 7527
(2007/10/03)

A novel synthesis of β,β-dibromostyrenes
A new simple and efficient transformation of aromatic aldehydes to β,β-dibromostyrenes and arylbromoacetylenes is described. The olefination procedure was conducted under mild conditions and in good yields.
Shastin,Korotchenko,Nenajdenko,Balenkova
p. 2081 - 2084
(2007/10/03)

Novel synthesis of unsymmetrical azines from semicarbazones and aldehydes
A new synthesis of unsymmetrical azines utilizing semicarbazones and aldehyde is described.
Zhongjiao,Weiguo,Weiqi,Jiajun
p. 125 - 129
(2007/10/03)

A novel synthetic approach to dichlorostyrenes
We found that N-unsubstituted hydrazones of aromatic aldehydes can be easily converted to the corresponding 1,1-dichlorostyrenes in the reaction with carbon tetrachloride using copper (I) chloride as catalyst. Factors affecting the route of the reaction and yields of the products were investigated. A proposed mechanism for the reaction is discussed. (C) 2000 Published by Elsevier Science Ltd.
Shastin,Korotchenko,Nenajdenko,Balenkova
p. 6557 - 6563
(2007/10/03)

Pyrazolidine derivative radical scavenger brain-infarction depressant and brain-edema depressant
A pyrazolidine derivative or a salt thereof in accordance with the present invention is expressed by the following formula 1: STR1 wherein A represents a group expressed by --CH2 --, --CO--, --CS--, --CH2 CO--, or --CH=CH--CO--; B represents a group expressed by --O-- or --NH--; n is an integer of 1 or 2; R represents an alkenyl group; and R1 and R2 represent a lower alkyl or benzyl group. The pyrazolidine derivative above mentioned, as a radical scavenger, has antioxidant effect and lipid peroxidation inhibitory activity so as to be available for inhibiting brain infarction or brain edema.
-
(2008/06/13)

Chemistry of diazocarbonyl compounds. IV. Synthesis and chemical properties of triphenylphosphoranylidenhydrazones of alkyl oxocarboxylates
Alkyl 3-diazo-2-oxopropanoates react with triphenylphosphine to form corresponding triphenylphosphoranylidenehydrazones. The latter form symmetrical azines with aromatic aldehydes. Ethyl (Z)-5-aryl-5-hydroxy-2-diazo-3-oxo-4-pentenoates under the action of
Zalesov,Vyaznikova,Andreichikov
p. 705 - 709
(2007/10/03)

Synthesis and cytotoxic evaluation of some styryl ketones and related compounds
A number of 1-aryl-4-methyl-1-penten-3-ones 1 were converted to the corresponding Mannich bases 2 and analogues 3.Attempts to form the azines 4 from several members in series 1 led to the isolation of the corresponding pyrazolines 5 or aryl aldehyde azine
Dimmock, J.R.,Kumar, P.,Quail, J.W.,Pugazhenthi, U.,Yang, J.,et al.
p. 209 - 218
(2007/10/02)

Oxidative Transformations of Aldazines and Ketazines with Organic Peroxyacids
Oxidation of aromatic aldazines and ketazines with various peroxycarboxylic acids was investigated.It was found that one part of azine molecule 2 was converted into carbonyl compound 1 or related acid 3 while the second part was transformed into carboxylic ester 4 related to peroxyacid used as an oxidant.It was revealed that aromatic azines could be used as a source of diazaarylmethanes and mechanisms of reactions studied were postulated. aldazines, carboxylic esters, ketazines, oxidation, peroxycarboxylic acids
Mlochowski, J.,Giurg, M.
p. 2333 - 2342
(2007/10/02)

Mesogenic Properties as an Analytical Tool for the Pyrolytic Transformation of Substituted Aryl Aldehyde Semicarbazones to Corresponding Benzalazines
The evaluation of semicarbazones for the mesogenic properties revealed that it undergoes transformation to azine at elevated temperatures.The transformation products were identified by modern tools.The diazines of 4-n-alkoxy benzaldehydes are reported to be mesogenic.It was planned to use mesomorphism as a tool for analysis.We had established that transformation of a semicarbazone of aldehyde gives diazine.With this in view fourteen 4-n-alkoxybenzaldehyde semicarbazones were synthesized and heated at 260 deg C in an oil bath.The pyrolized products were purified and evaluated for their mesogenic properties.The mesogenic properties of pyrolized products exactly tally with the diazines reported by Shaw and Brown.A few diazines which were not reported are also obtained in present study and are characterized.They also exhibit mesomorphism.The study indicates that if the transformation products can be designed which are conducive to mesomorphism, the mesogenic properties can be the tool to understand it and identify the products.The calorimetric study is carried out and enthalpy values are obtained to understand thermodynamic behavior.
Chudgar, N. K.,Shah, S. N.,Vora, R. A.
p. 237 - 242
(2007/10/02)

CHLOROSULFONATION OF DIARYL AZINES
Benzaldehyde- and o-, m-, p-anisaldehyde azines; thiophene-2-carboxaldehyde, and biphenyl-4-carboxaldehyde azines (1-8) reacted with excess chlorosulfonic acid to give the disulphonyl chlorides (1a-8a).These were condensed with amines and hydrazine to give 27 derivatives, (Table I) for biocidal evaluation.The orientation of sulfonation is discussed in relation to the stereoelectronic factors and the spectral data.Attempted chlorosulfonation of furan-2-carboxaldehyde azine (9) gave an impure product which could not be clearly characterized as the morpholidate derivative.
Cremlyn, Richard J.,Swinbourne, Frederick J.,Graham, Stephen,Cavaleiro, Jose A. S.,Domingues, Fernando J.,Dias, Maribel
p. 57 - 65
(2007/10/02)

Mesomorphic Properties of the 4,4'-Di(n) Alkoxybenzalazines
We have reinvestigated the mesomorphic properties of the 4,4'-Di(n) alkoxybenzalazines, first reported by Shaw and Brown.Thirteen members of the series were prepared with the number (n) of carbon atoms varying from 1 to 16.A Nematic phase was always observed except for n >/= 13; a monotropic smectic phase was observed for n = 5, 6 and another smectic phase for n >/= 10.The compounds were examined with a polarizing microscope and heats of transition determined using a DSC-2 calorimeter.Our results differ from those of Shaw and Brown as they did not observe the monotropic smectic phase for n = 5, 6.They also cite a smectic phase for n = 7, 8, 9, 10 whereas we observe a smectic phase only for n >/= 10 (n = 9, was not synthesized by us).The temperature given by Shaw and Brown for the crystal-smectic transitions for n = 7, 8, 9, 10 we identify as the temperatures of crystal-crystal transitions.Of these only n = 10 has a smectic phase and the transition temperature is considerably higher than that given by Shaw and Brown.
Bennur, S. C.,Gault, J. D.,Kroin, T.,Ouriques, G. R.,Taylor, T. R.
p. 267 - 276
(2007/10/02)

THE EFFECT OF ARYL SUBSTITUENTS ON ARYLCARBENE REACTIVITY
Substituted (p-MeO, p-Me, H, p-Cl, p-Br, m-Br, m-MeO, 3,4-Cl2, p-CO2Me, m-CN and p-CN) monophenylcarbenes are generated in a binary mixture of substrates (methanol, cis-4-methyl-2-pentene and cyclohexane) and the relative rate of O - H insertion into methanol to stereospecific cyclopropanation of the olefin to C - H insertion into cyclohexane are calculated from the ratios of products and substrates.It is found (i) that the reactivities of the substrates decrease in the order of methanol, olefin and cyclohexane and (ii) that electron-donating substituents generally lead to reaction with the more reactive substrates while the reaction with the less reactive substrates is favoured in the case of electron-withdrawing substituents.These results are interpreted in terms of the change in the electrophilicity of the singlet arylcarbene by the substituents rather than the change in the singlet-triplet equilibrium.
Tomioka, Hideo,Tabayashi, Kazuo,Ozaki, Yasuji,Izawa, Yasuji
p. 1435 - 1440
(2007/10/02)