- Ruthenium(ii)-catalysed 1,2-selective hydroboration of aldazines
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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
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supporting information
p. 7147 - 7151
(2021/08/30)
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- Unusual synthesis of azines and their oxidative degradation to carboxylic acid using iodobenzene diacetate
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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.
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supporting information
p. 439 - 446
(2018/02/06)
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- 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
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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
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p. 104973 - 104980
(2015/12/26)
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- Solvent-Free Green Synthesis of Azines and Their Conversion to 2,5-Disubstituted-1,3,4-thiadiazoles
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A solvent-free, clean, and efficient method has been developed for the synthesis of 2,5-disubstituted-1,3,4-thiadiazoles via azines. This approach exploits the synthetic potential of clean reactions and offers many advantages such as excellent product yie
- Shridevi, D. Doddramappa,Ningaiah, Srikantamurthy,Kuduva, Narayan U.,Yhya, Raad K.,Rai, Kuriya M. Lokanatha
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supporting information
p. 2869 - 2875
(2015/12/23)
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- An expeditious synthetic approach towards the synthesis of Bis-Schiff bases (aldazines) using ultrasound
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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
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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
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supporting information
p. 1786 - 1790
(2014/08/05)
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- Synthesis and characterization of novel organonickel and organocobalt complexes via carbonechlorine bond activation
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The ortho-metalated nickel(II) complexes 3, 4, 7 and 8 were obtained by the reaction of ortho-halogeno aromatic bis-Schiff bases 1, 2, 5 and 6 with the stoichiometric amount of Ni(PM-3)4. The combination of 5 and 6 with two equivalents of Ni(PM-3)4 resulted in oxidative addition of the double CeCl bonds to afford ortho-bis-chelated nickel(II) complexes 9 and 10. The reaction of 6 with Co(PM-3)4 gave rise to dinuclear ortho-metalated cobalt(II) complex 12 through CeCl bond activation while the reaction of 5 with Co(PM-3)4 delivered bis-chelated cobalt(I) complex 11 through both CeCl and CeH bond activation. The structures of complexes 3, 4, 8, 9, 11 and 12 were determined by X-ray single crystal diffraction. The catalytic activity of bis-chelated cobalt(I) complex 11 as catalyst for C,C-coupling reaction was explored.
- Li, Junye,Li, Xiaoyan,Sun, Hongjian
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p. 114 - 122
(2013/10/08)
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- Synthesis of 1H-indazole: A combination of experimental and theoretical studies
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A new practical synthesis of 1H-indazole is presented. A previous mechanism for the cyclization step is proved to be nonfeasible and a hydrogen bond propelled mechanism is proposed. The new mechanism is suitable for similar cyclization, and a new reaction is predicted. Springer Science+Business Media B.V. 2012.
- Chen, Xinzhi,Zhou, Shaodong,Qian, Chao,He, Chaohong
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p. 1619 - 1628
(2012/10/30)
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- Microwave-assisted synthesis of 1-hydrazinophosphonates via the reaction of aldazines with dialkyl phosphite
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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
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experimental part
p. 304 - 308
(2012/07/27)
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- Spectroscopic and theoretical studies on symmetric aryl azines
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Azines, which closely resemble azobenzenes, have important applications in the field of nonlinear optics. NMR and IR spectroscopic study of some symmetric aryl azines has been undertaken with the aid of ab initio theoretical calculations. All data indicated that the structure of azine and substituted azines is the symmetric trans form.
- Karthikeyan, Balakrishnan,Jayabharathi, Jayaraman,Thanikachalam, Venugopal
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p. 636 - 638
(2008/09/17)
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- Reaction of CBrF2-CBrF2 with hydrazones of aromatic aldehydes. Novel efficient synthesis of fluorocontaining alkanes, alkenes and alkynes
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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)
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- Reactions of 1,3-dipolar aldazines and ketazines with the dipolarophile dimethyl acetylenedicarboxylate
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The prepared aldazines (aldehyde azines) and ketazines (ketone azines) were allowed to react with 2 mol of the acetylene derivative. The first products formed were pentalene azine derivatives, which in some cases underwent skeletal rearrangment into acycl
- El-Alali, Abdullah,Al-Kamali, Ahmed S.
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p. 1293 - 1301
(2007/10/03)
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- Reaction of aldehydes with hydrazine in the system sulfur-alkali
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Dissolution of sulfur in the system hydrazine hydrate-alkali leads to strong activation of hydrazine, so that the latter readily reacts at room temperature with aldehydes of the aromatic and thiophene series to give the corresponding aldehyde azines in high yield. The mechanism of activating effect of sulfur is discussed.
- Russavskaya,Grabel'nykh,Levanova,Sukhomazova,Deryagina
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p. 1498 - 1500
(2007/10/03)
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- A novel approach to fluoro-containing alkenes
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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
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p. 7519 - 7527
(2007/10/03)
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- A novel synthesis of β,β-dibromostyrenes
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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
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p. 2081 - 2084
(2007/10/03)
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- One-pot oxidation of azomethine compounds into arenecarboxylic acids
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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
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p. 3151 - 3159
(2007/10/03)
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- ZEOLITE-CuNaY CATALYZED DECOMPOSITION OF ARYLDIAZOMETHANE
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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
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p. 1895 - 1898
(2007/10/02)
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- 1,2,4,5-Tetrazines
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The substituted tetrazines of the formula: STR1 and of the formula: STR2 wherein: R1, R2 and R4 each represent hydrogen, phenyl, alkyl of 1 to 6 carbon atoms, or alkenyl or alkynyl of 3 to 6 carbon atoms, each of which may be unsubstituted or substituted by one or more halogen atoms, hydroxy groups, cyano groups, carboxy groups, alkoxycarbonyl groups of 2 to 5 carbon atoms, or alkoxy groups of 1 to 4 carbon atoms; or R1 and R2 together represent a single bond; R3 represents alkyl of 1 to 6 carbon atoms, cycloalkyl of 3 to 7 carbon atoms, phenyl or phenylalkyl of 7 to 10 carbon atoms, each of which may be unsubstituted or substituted by one or more halogen atoms, alkyl or alkoxy groups of 1 to 6 carbon atoms, nitro groups, cyano groups, mercapto groups, or alkylmercapto groups of 1 to 4 carbon atoms; and R6 represents a phenyl group substituted in at least the 2-position by fluorine, chlorine, bromine or iodine; are effective to combat acarids and their eggs.
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