- 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)
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- 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; 0044-0046
(2019/05/15)
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- Mechanistic Studies on the Michael Addition of Amines and Hydrazines to Nitrostyrenes: Nitroalkane Elimination via a Retro-aza-Henry-Type Process
-
In this article we report on the mechanistic studies of the Michael addition of amines and hydrazines to nitrostyrenes. Under the present conditions, the corresponding N-alkyl/aryl substituted benzyl imines and N-methyl/phenyl substituted benzyl hydrazones were observed via a retro-aza-Henry-type process. By combining organic synthesis and characterization experiments with computational chemistry calculations, we reveal that this reaction proceeds via a protic solvent-mediated mechanism. Experiments in deuterated methanol CD3OD reveal the synthesis and isolation of the corresponding deuterated intermediated Michael adduct, results that support the proposed slovent-mediated pathway. From the synthetic point of view, the reaction occurs under mild, noncatalytic conditions and can be used as a useful platform to yield the biologically important N-methyl pyrazoles in a one-pot manner, simple starting with the corresponding nitrostyrenes and the methylhydrazine.
- Kallitsakis, Michael G.,Tancini, Peter D.,Dixit, Mudit,Mpourmpakis, Giannis,Lykakis, Ioannis N.
-
supporting information
p. 1176 - 1184
(2018/02/09)
-
- 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)
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- 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.
-
-
- 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
-
-
- 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
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p. 8415 - 8419
(2018/05/23)
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- 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
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p. 1499 - 1507
(2016/07/06)
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- 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 0025; 0026
(2016/12/01)
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- Reaction of fenchone hydrazone with diselenium dibromide: Novel formation of bicyclic diselenide
-
Bicyclic diselenide containing a norbornane skeleton was synthesized by the reaction of fenchone hydrazone with Se2Br2. Initially formed selenofenchone further reacted with another molar amount of Se2Br2 to afford Wagner-Meerwein rearranged diselenide. Camphor hydrazone also reacted with Se2Br2 to afford the corresponding diselenide, whereas no rearranged product was formed.
- Okuma, Kentaro,Munakata, Kazunori,Matsui, Hiroyuki,Nagahora, Noriyoshi,Shioji, Kosei
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p. 473 - 480
(2014/03/21)
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- 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.
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p. 1200 - 1205
(2014/02/14)
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- 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)
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- 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)
-
- 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
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p. 2607 - 2614
(2011/08/07)
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- 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
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experimental part
p. 636 - 638
(2009/05/11)
-
- Synthesis and X-ray crystallographic analysis of some 1,6-dihydro-1,2,4,5- tetrazines
-
Eight 1,6-dihydro-1,2,4,5-tetrazines (2a-2h) were synthesised by reaction of sodium borohydride with 3,6-substituted-1,2,4,5-tetrazines. The structure of 2c was confirmed by single-crystal X-ray diffraction. The central six-membered ring of 2c has an obvious unsymmetrical boat conformation. It could be considered that the molecule has a homoaromaticity.
- Hu, Wei-Xiao,Xu, Feng
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p. 797 - 799
(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.
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p. 907 - 913
(2007/10/03)
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- 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
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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.
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p. 1339 - 1345
(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)
-
- 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 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)
-
- 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)
-
- Thermolysis of semicarbazones to the corresponding azines through reactive N-substituted isocyanate intermediates
-
Thermolysis of semicarbazones (I) to azines (II) occurs through reactive N-substituted isocyanate intermediates (Ia) which can be converted in situ to carbamates and N-substituted ureas.
- Shah,Chudgar
-
p. 657 - 664
(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)
-
- ZEOLITE-CuNaY CATALYZED DECOMPOSITION OF ARYLDIAZOMETHANE
-
Decomposition of aryldiazomethanes is catalyzed by copper ion-exchanged Y-type zeolite to afford cis-1,2-diarylethylenes in high selectivity.The catalytic activity and selectivity are found to be affected by the exchange level of copper ions in zeolite and the solvent used.
- Onaka, Makoto,Kita, Hiroshi,Izumi, Yusuke
-
p. 1895 - 1898
(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)
-
- Charge-tansfer complexes of substituted aromatic azines and ?-acceptors
-
Charge-transfer complexes of symmetrically substituted aromatic azines with tetracyanoethylene (TCNE) and 1,4-benzoquinones in methylene chloride have been investigated spectrophotometrically.The spectral data, molar extinction coefficients and transition energies of the complexes formed as well as the ionization potentials of the electron donors are reported.Both BENSI-HILDEBRAND and JOB methods have been applied in determination of association and apparent formation constants respectively.Substituent effect on charge-transfer equilibria of the substituted azines has been discussed.
- Mourad, Aboul-Fetouh E.
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p. 933 - 938
(2007/10/02)
-
- Unsaturated Compounds containing Nitrogen. Part 4. Further Reactions of 1-Chloro-2,3-diazabutadienes with S-Nucleophiles
-
1-Chloro-1,4-diaryl-2,3-diazabutadienes (Ar1CCl=NN=CHAr2), prepared by the reaction of thionyl chloride with aroylhydrazones (Ar1CONHN=CHAr2), react with thiosemicarbazide or thiocarbohydrazide to give 2-arylidenehydrazino-5-aryl-1,3,4-thiadiazoles, and with potassium thiocyanate to give 1-thiocyanato-1,4-diaryl-2,3-diazabutadienes which isomerize thermally to arylideneamino-5-aryl-1,3,4-thiadiazoles. 1-Chloro-1,4-diphenyl-2,3-diazabutadiene reacts with potassium ethylxanthate to give a 1-ethylxanthyl-2,3-diazabutadiene which on pyrolysis yields 2,5-diphenyl-1,3,4-thiadiazole.
- Flowers, William T.,Robinson, John F.,Taylor, David R.,Tipping, Anthony E.
-
p. 349 - 355
(2007/10/02)
-
- trans-2,3-Di-tert-butylthiirane 1,1-Dioxide and 2,5-Di-tert-butyl-2,5-dihydro-1,3,4-thiadiazole 1,1-Dioxides from tert-Butyldiazomethane and Sulfur Dioxide. Solvent Effects and Mechanisms of the Staudinger-Pfenninger-Reaction
-
When allowed to react with sulfur dioxide tert-butyldiazomethane formed not only trans-di-tert-butylthiirane 1,1-dioxide (3) but also the diastereomeric 2,5-dihydro-1,3,4-thiadiazole 1,1-dioxides 7e which under base-catalysis rearranged to the 2,3-dihydro-1,3,4-thiadiazole 1,1-dioxide 11.The structures were deduced from IR, UV, and 1H-NMR-spectra, and from the products obtained after loss sulfur dioxide.Whereas increase of the solvent polarity favoured 3 over 7e, the diastereomer ratio cis-7e/trans-7e remained virtually unaffected.The ratio of thiirane 1,1-dioxide 3 to dihydrothiadiazole 1,1-dioxides did not depend on whether the intermediate tert-butylsulfene 6e had been generated from 5e and sulfur dioxide or from 2,2-dimethylpropane sulfonylchloride (14) and triethylamine.In contrast to reports in the literature, the reaction of the phenyldiazoalkanes 5f and 5h with sulfur dioxide afforded cis/trans ratios of the thiirane 1,1-dioxides 9f and 9h, respectively, which were only slightly influenced by the solvent.Apparently, the dihydrothiadiazole 1,1-dioxides 7 and hence their decomposition products, the azines 8 (as far as these do not arise from the direct decomposition of the diazo compounds), are the result of a cycloaddition between the diazoalkane 5 and the sulfene 6.In contrast, the thiirane 1,1-dioxides 9 seem to originate via the zwitterions 20 the formation of which is favoured over the cycloaddition by solvents of high polarity, by the presence of aryl substituents at the sulfene, as well as by the lack of alkyl groups.The dichotomy in the behaviour of sulfenes towards diazoalkanes can be traced back to the existence of two low-lying sulfene MO's, only one of which exhibits ?-symmetry.
- Quast, Helmut,Kees, Frieder
-
p. 787 - 801
(2007/10/02)
-
- Base-catalysed Condensation of Aromatic Aldehydes with 4,5-Dihydro-6-methylpyridazin-3(2H)-one
-
4-Arylmethyl-6-methylpyridazin-3(2H)-ones (IIIa-d) have been prepared by the condensation of aromatic aldehydes with 4,5-dihydro-6-methylpyridazin-3(2H)-one (I) in basic media.Compounds IIIa-d react in the lactim form with POCl3 to give 4-arylmethyl-3-chloro-6-methylpyridazines (Va-d), while these react in the lactam form with dimethyl sulphate to give 4-arylmethyl-2,6-dimethylpyridazin-3(2H)-ones (VIa-d).Compound IIId reacts with ethyl bromoacetate in the presence of sodium ethoxide to give the ethyl ester (VIIa) which reacts with benzylamine and hydrazine hydrate togive the corresponding N-benzylamide (VIIc) and hydrazide (VIId).The ester (VIIa) is readily hydrolysed to the corresponding acid (VIIb).
- Ismail, M. F.,El Khamry, A. A.,Shams, N. A.,El Sawy, O. M.
-
p. 203 - 205
(2007/10/02)
-