1068-57-1Relevant articles and documents
Asymmetric Synthesis and Antitumor Activity of Spiro-Oxadiazole Derivatives from 1,4:3,6-Dianhydro-D-fructose
Xu, Wenke,Ge, Yongxun,Hou, Yu,Liu, Yingju,Hua, Yingchun,Han, Weiwei,Qin, Zhiyan,Liu, Fengwu
, p. 1437 - 144 (2017)
A series of spiro-oxadiazoles were synthesized from 1,4:3,6-dianhydro-D-fructose and hydrazides via a stereo- selective two-step reaction sequence. The structures of newly synthesized compounds were established by spectral analysis. The absolute configuration of compound 2a was further confirmed by single crystal X-ray analysis. All the synthesized compounds were screened for their in vitro antitumor activity, showing that these compounds have poor inhibitory activities against A549, MGC-803 tumor cells.
Facile synthesis of new 10-substituted-5H-naphtho[1,2-e][1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-5-ones
Khalafy, Jabbar,Mohammadlou, Mahsa,Mahmoody, Miri,Salami, Fatemeh,Poursattar Marjani, Ahmad
, p. 1528 - 1530 (2015)
The reaction of 2-bromo-1,4-naphthoquinone with 4-amino-5-aryl-4H-1,2,4-triazole-3-thiols in ethanol at 50 °C gave the corresponding 2-[(4-amino-5-aryl-4H-1,2,4-triazol-3-yl)thio]naphthalene-1,4-diones. Their treatment with EtOH/HCl under reflux conditions produced 10-substituted-5H-naphtho[1,2-e][1,2,4]triazolo[3,4-b][1,3,4]thiadiazin-5-ones through intramolecular cyclization.
Consecutive hydrazino-Ugi-azide reactions: Synthesis of acylhydrazines bearing 1,5-disubstituted tetrazoles
De Fátima Barreto, Angélica S.,Dos Santos, Veronica Alves,Zandrade, Carlos Kleber
, p. 2596 - 2602 (2017)
Isocyanide-based multicomponent reactions (IMCRs) allow the construction of relatively complex molecules through a one-pot synthesis. The combination of IMCRs in a consecutive or sequential fashion further extends the complexity of the molecules obtained. Herein, we report the efficient application of this approach to the synthesis of acylhydrazines bearing 1,5-disubstituted tetrazoles. Our strategy was accomplished in only three steps: first, a one-pot hydrazino-Ugi-azide four-component reaction; second a hydrazinolysis and finally an additional hydrazino-Ugi-azide reaction. This sequence provides the title compounds in moderate to excellent yields. The products synthesized herein contain functional groups within their structures that can be easily modified to obtain new acylhydrazino 1,5-disubstituted tetrazoles.
Novel route for the transformation of a pyrimidine ring using hydrazides
Danagulyan,Tadevosyan,Tamazyan,Panosyan
, p. 233 - 245 (2006)
It has been shown from X-ray structural analytical data that the reaction of 2-ethoxycarbonylmethyl-1,4,6-trimethylpyrimidinium iodide with carboxylic acid hydrazides gives pyrazolo[1,5-a]pyrimidine derivatives and not the isomeric triazolo[4,3-a]pyridines previously reported. This novel and previously unreported rearrangement of 1,2-dialkylpyrimidinium salts occurs via recyclization of the pyrimidine ring with inclusion of a fragment of the nucleophilic reagent into the transformation product. 2006 Springer Science+Business Media, Inc.
Acid hydrolysis of 1,6-dihydro-4-amino-3-methyl-6-phenyl-1,2,4-triazin- 5(4H)-one (1,6-dihydrometamitron)
Ludvik,Jirkovsky,Urban,Zuman
, p. 3879 - 3885 (1999)
Metamitron (1) does not undergo hydrolysis at pH 1-8 and up to 5 M H2SO4. The product of its two-electron reduction, 1,6-dihydrometamitron (2), on the other hand, undergoes at pH 22+) predominating in strongly acidic media undergoes hydrolysis slower than the species bearing one less proton (AH+]. The latter most reactive species is present in highest concentration in solutions of pH between 0 and 2. This species is protonated on the 2,3- azomethine bond and yields as final products 2-hydrazino-2-phenylacetic acid (4) and a cethydrazide (5). Kinetic, polarographic, and spectrophotometric measurements indicated for the first dissociation an average value pK(a) = - 0.8, for the second pK(a) = 0.95. These observations together with the easy reduction of the 1,6-bond in metamitron (1) indicate that in nature the cleavage of metamitron may be preceded by its reduction to 1,6- dihydrometamitron (2), which is then hydrolyzed. Thus, anaerobic, reductive conditions are likely preferable for the total microbial degradation of metamitron.
Catalytic conversion of glycerol to allyl alcohol; Effect of a sacrificial reductant on the product yield
Sanchez, Gizelle,Friggieri, Jarrod,Adesina, Adesoji A.,Dlugogorski, Bogdan Z.,Kennedy, Eric M.,Stockenhuber, Michael
, p. 3090 - 3098 (2014)
A continuous process for the conversion of glycerol to allyl alcohol, where ammonia or organic acids are added to the feed as sacrificial reductants, was investigated. Significant enhancement on the rate of formation and yield of the allyl alcohol is observed with some of the reducing agents examined over an alumina-supported iron catalyst. Optimising the molar ratio of the reductant relative to feed glycerol results in an increase in the yield of allyl alcohol from 9% (in the absence of additives) to 11.3% with ammonia, 15.1% with ammonium hydroxide, 17.8% with oxalic acid and 19.5% with formic acid. Moreover, the addition of other organic acids, which are produced in a typical glycerol conversion experiment, was studied. However, acetic and propanoic acids had little effect on the rate of formation of allyl alcohol. Analysis of the product distribution in the liquid and gas phases when oxalic and formic acids were added suggests a two-step process for the formation of allyl alcohol under the operating conditions of the reaction; the initial step involves the dehydration of glycerol while the second comprises the reduction of the species produced in step one. the Partner Organisations 2014.
Synthesis and in vitro leishmanicidal activity of some hydrazides and their analogues
Khan, Khalid Mohammad,Rasheed, Maimona,Ullah, Zia,Hayat, Safdar,Kaukab, Farhana,Choudhary, M. Iqbal,Ur-Rahman, Atta,Perveen, Shahnaz
, p. 1381 - 1387 (2003)
Twenty-one hydrazides were synthesized by treating different esters with hydrazine hydrate. Substituted hydrazides were obtained by treating hydrazides with alkyl/aryl/acyl halides. Some of these compounds exhibit potential in vitro leishmanicidal activity. The structures of all the synthesized compounds were confirmed by spectroscopic analysis.
Bioisosteric approach to elucidation of binding of the acetate group of a moth sex pheromone component to its receptor
Gustavsson, Anna-Lena,Tuvesson, Malena,Larsson, Mattias C.,Wenqi, Wu,Hansson, Bill S.,Liljefors, Tommy
, p. 2755 - 2776 (1997)
A number of analogs of (Z)-5-decenyl acetate, a pheromone component of the turnip moth, Agrotis segetum, in which the acetate group has been replaced by functional groups that may function as bioisosters, have been synthesized and tested using single-cell electrophysiology. The activities have been interpreted in terms of the molecular electrostatic potentials of the polar functional group as calculated by ab initio quantum mechanical calculations. It is concluded that both oxygens of the acetate group in (Z)-5-decenyl acetate contribute to the interactions between the pheromone component and its receptor. Furthermore, the results indicate that the crucial interaction between the carbonyl group and the receptor, which is most probably a hydrogen bonding interaction, takes place in a direction pointing away from the hydrocarbon chain of the pheromone component.
Catalytic oxygen atom transfer promoted by tethered Mo(VI) dioxido complexes onto silica-coated magnetic nanoparticles
Colaiezzi, Roberta,Crucianelli, Marcello,Di Giuseppe, Andrea,Ferella, Francesco,Lazzarini, Andrea,Paolucci, Valentina
, (2021/11/30)
The preparation of three novel active and stable magnetic nanocatalysts for the selective liquid-phase oxidation of several olefins, has been reported. The heterogeneous systems are based on the coordination of cis-MoO2 moiety onto three different SCMNP@Si-(L1-L3) magnetically active supports, functionalized with silylated acylpyrazolonate ligands L1, L2 and L3. Nanocatalysts thoroughly characterized by ATR-IR spectroscopy, TGA and ICP-MS analyses, showed excellent catalytic performances in the oxidation of conjugated or unconjugated olefins either in organic or in aqueous solvents. The good magnetic properties of these catalytic systems allow their easy recyclability, from the reaction mixture, and reuse over five runs without significant decrease in the activity, either in organic or water solvent, demonstrating their versatility and robustness.
Synthesis of novel seco-acyclo-N-diazolyl-thione nucleosides analogous derived from acetic acid: characterization, complex formation with ions Pb(II), Hg(II) and antibacterial activity
Chehrouri, Manel,Othman, Adil A.
, (2021/08/09)
Three diazoles namely 5-methyl-1,3,4-oxadiazole -2(3H)-thione, 5-methyl-1,3,4-thiadiazol-2(3H)-thione and 4-amino-5-methyl-2H-1,2,4-triazole-3-thiol were synthesized from acetic acid or ethyl acetate. Seco-acyclo-N-nucleoside analogous was synthesized by condensation of 1,3-benzylidine-glyceryl-2-tosylate with the three diazoles. Structural proof was based upon IR, 1H-NMR, 13C-NMR spectroscopy and MS measurements. The tendency to form complex between 1,3,4-oxadiazole and 1,3,4-thiadiazoles and Pb(II) and Hg(II) ions was achieved, and their structures were assigned by observing some changes in physical properties such as, MP, coloration, Rf (TLC), IR and UV spectroscopy. Most compounds were tested in vitro against Gram-positive and Gram-negative bacteria and showed variable activity. Hg2+ complexes of oxadiazole and thiadiazole derivatives exhibited appreciable antibacterial effect at lower MIC, compatible to the reference vancomycin. Similarly, oxadiazole-nucleoside exhibited high effect on Gram-positive bacteria. Graphic abstract: [Figure not available: see fulltext.]
N-Amino-1,8-Naphthalimide is a Regenerated Protecting Group for Selective Synthesis of Mono-N-Substituted Hydrazines and Hydrazides
Manoj Kumar, Mesram,Venkataramana, Parikibanda,Yadagiri Swamy, Parikibanda,Chityala, Yadaiah
supporting information, p. 17713 - 17721 (2021/11/10)
A new route to synthesis of various mono-N-substituted hydrazines and hydrazides by involving in a new C?N bond formation by using N-amino-1,8-naphthalimide as a regenerated precursor was invented. Aniline and phenylhydrazines are reproduced upon reacting these individually with 1,8-naphthalic anhydride followed by hydrazinolysis. The practicality and simplicity of this C?N dihalo alkanes; developed a synthon for bond formation protocol was exemplified to various hydrazines and hydrazides. N-amino-1,8-naphthalimide is suitable synthon for transformation for selective formation of mono-substituted hydrazine and hydrazide derivatives. Those are selective mono-amidation of hydrazine with acid halides; mono-N-substituted hydrazones from aldehydes; synthesis of N-aminoazacycloalkanes from acetohydrazide scaffold and inserted to hydroxy derivatives; distinct synthesis of N,N-dibenzylhydrazines and N-benzylhydrazines from benzyl halides; synthesis of N-amino-amino acids from α-halo esters. Ecofriendly reagent N-amino-1,8-naphthalimide was regenerated with good yields by the hydrazinolysis in all procedures.
