100726-23-6Relevant academic research and scientific papers
Experimental and quantum chemical studies of the structural and spectral properties of novel diazenyl formazans
Tezcan, Habibe,?en?z, Hülya,Tokay, Nesrin
, p. 171 - 183 (2019)
A new series of 3-(p-substitutedphenyl)-5-phenyl-1-(4-phenyldiazenyl)phenylformazans were synthesized by coupling p-substituted phenyl or pyridinylhydrazones with p-aminoazobenzene diazonium chloride. All compounds were characterized by FT-IR, UV–Vis, 1H NMR, and 13C NMR spectroscopic techniques, and HR-MS. DFT was used to calculate the molecular structures and 1H and 13C chemical shift values of the synthesized compounds with PBE1PBE functional and 6-311G(2d,2p)basis set combination. The IR spectra of the novel formazans were calculated using DFT at PBE1PBE/6-311G(d,p)level of theory. The electronic absorption spectra of the optimized structures were evaluated by TD-DFT method at PBE1PBE/6-311G(2d,2p)level of theory. The absorption spectra of the synthesized diazenyl formazans were investigated in three different solvents. A good correlation was established between the experimental data and calculated results.
A novel chemoselective synthesis of 3H-spiro[isobenzofuran-1,3'-pyrazole] derivatives by oxidative cleavage of their corresponding dihydroindeno[1,2-c]pyrazoles
Mohammadizadeh, Mohammad Reza,Basti, Fatemeh
, p. 1171 - 1176 (2015)
Abstract This paper reports a new and simple procedure for the synthesis of 3H-spiro[isobenzofuran-1,3'-pyrazole] derivatives by reacting 1-benzylidene-2-phenylhydrazine derivatives with ninhydrin in acetic acid medium at room temperature followed by oxidative cleavage of their corresponding dihydroindeno[1,2-c]pyrazoles. 1-Benzylidene-2-phenylhydrazine derivatives were prepared via the reaction between phenylhydrazine and benzaldehyde derivatives. Easy procedure, mild reaction conditions, high yields in short reaction times, availability of starting materials, and no formation of by-product are the advantages of this approach.
Sequential [3+2] annulation reaction of prop-2-ynylsulfonium salts and hydrazonyl chlorides: Synthesis of pyrazoles containing functional motifs
Jia, Tingting,Liu, Shourong,Shao, Jiaan,Shi, Tao,Wu, Zhaoxiao,Zeng, Linghui,Zhang, Chong,Zhang, Jiankang,Zhu, Huajian,Zhuang, Rangxiao
supporting information, p. 8460 - 8463 (2021/09/08)
A novel sequential [3+2] annulation reaction has been developed using prop-2-ynylsulfonium salts and hydrazonyl chlorides, affording a series of pyrazoles with functional motifs that can be post modified in the preparation of various drugs or drug candidates. Further transformation and gram-scale operations could also be achieved efficiently. This journal is
Synthesis of 1,1′-([1,1′-Biphenyl]-4,4′-diyl)bis(3-aryl-5-phenylformazans) and 1,1′-([1,1′-Biphenyl]-4,4′-diyl)bis(3-aryl-5-phenyl-5,6-dihydro-1,2,4,5-tetrazin-1-ium) Perchlorates
Alalwan, D. H. K.,Jassim, T.,Kostryukov, S. G.,Kozlov, A. Sh.,Masterova, Yu. Yu.,Tezikova, V. S.
, p. 1600 - 1607 (2021/12/13)
Abstract: New bis-formazans and bis(5,6-dihydro-1,2,4,5-tetrazin-1-ium) perchlorates were synthesized with high yields under mild conditions. 1,1′-([1,1′-Biphenyl]-4,4′-diyl)bis(3-aryl-5-phenylformazans) were obtained by diazo coupling of para-substituted benzaldehyde phenylhydrazones with [1,1′-biphenyl]-4,4′-bis(diazonium chloride). Treatment of the obtained bis-formazans with formaldehyde in the presence of perchloric acid in dioxane afforded 1,1′-([1,1′-biphenyl]-4,4′-diyl)bis(3-aryl-5-phenyl-5,6-dihydro-1,2,4,5-tetrazin-1-ium) diper-chlorates. The structure of the synthesized compounds was confirmed by elemental analyses and UV, IR, and 1H and 13C NMR spectra.
Acid-Mediated Three Component Assembly of 4-Fluoropyrazoles from α-Fluoronitroalkenes, Hydrazines, and Aldehydes
Ioffe, Sema L.,Motornov, Vladimir A.,Nelyubina, Yulia V.,Nenajdenko, Valentine G.,Tabolin, Andrey A.
, (2020/08/06)
A new approach for the synthesis of highly pharmaceutically relevant 4-fluoropyrazoles via oxidative annulation of α-fluoronitroalkenes with in situ prepared hydrazones was developed. The reaction is efficiently promoted by trifluoroacetic acid while atmo
Synthesis and Electrochemical Properties of 2-(4-R1-Phenyl)-6-(4-R2-phenyl)-4-phenyl-3,4-dihydro1,2,4,5-tetrazin-1(2H)-yls
Akhmatova, A. A.,Balandina, A. V.,Chernyaeva, O. Yu.,Kostryukov, S. G.,Kozlov, A. Sh.,Kraynov, E. V.,Lukshina, Yu. I.,Pryanichnikova, M. K.
, p. 341 - 351 (2020/04/27)
Abstract: A new methodology for creating electroactive components for organic batteries,based on the construction of a molecular platform including stable3,4-dihydro-1,2,4,5-tetrazin-1(2H)-ylradicals was described. A series of2-(4-R1-phenyl)-6-(4-R2-phenyl)-4-phenyl-3,4-dihydro-1,2,4,5-tetrazin-1(2H)-yls with substituents of various nature wasobtained. It was shown that the substituents R1 inthe aromatic ring at position 2 of the tetrazinyl fragment influence the valueof the oxidation potential in the radical, but do not influence the value of thereduction potentials, while the substituent R2 of thearomatic ring at position 6 influence the values of the reduction potentials andpractically do not influence oxidation potential values. Based on the obtainedelectrochemical data, a correlation structure–potential value was revealed forthe cathodic and anodic process, with the help of which triarylsubstituted3,4-dihydro-1,2,4,5-tetrazin-1(2H)-ylradicals with high values of the electrochemical gap were obtained.
Triarylverdazyl radicals as promising redox-active components of rechargeable organic batteries
Burtasov, A. A.,Chernyaeva, O. Yu.,Kostryukov, S. G.,Kozlov, A. Sh.,Pryanichnikova, M. K.,Tanaseichuk, B. S.
, p. 1321 - 1328 (2020/09/07)
A novel design of electroactive components of rechargeable organic batteries based on stable verdazyl radicals bearing various substituents is proposed. 3-Positioned aromatic substituents at the verdazyl moiety affect the reduction potentials and almost do not affect the oxidation potential, while 1-positioned aromatic substituents affect contrariwise the oxidation potential of this radical without any influence on the reduction potential. The acquired electrochemical data allowed us to reveal the structure—potential relationship for the cathodic and anodic processes, which provided the design of triarylverdazyl radicals possessing record-breaking parameters of the “electrochemical gap”.
Synthesis of hybrid polycycles containing fused hydroxy benzofuran and 1H-indazoles via a domino cyclization reaction
Janardhanan, Jith C.,James, Kiran,Puthuvakkal, Anisha,Bhaskaran, Rasmi P.,Suresh, Cherumuttathu H.,Praveen, Vakayil K.,Manoj, Narayanapillai,Babu, Beneesh P.
, p. 10166 - 10175 (2019/07/03)
A stoichiometry controlled domino cyclization reaction of hydrazone and p-benzoquinone to an angularly fused 3H-benzofuro[3,2-e]indazole core with an embedded oxygenated dibenzofuran framework under mild reaction conditions is disclosed. The reaction involves palladium catalyzed 5-hydroxy-1H-indazole formation followed by TFA mediated [3+2] annulation between the in situ formed 5-hydroxy-1H-indazole and p-benzoquinone. The developed method is attractive because of the concomitant formation of two heterocyclic rings with consecutive multiple bond forming events that include two C-C, one C-N and one C-O bonds. Spectroscopic and theoretical studies of the blue emissive benzofuroindazole derivatives have also been described.
Stereospecific copper(II)-catalyzed tandem ring opening/oxidative alkylation of donor-acceptor cyclopropanes with hydrazones: Synthesis of tetrahydropyridazines
Mishra, Manmath,De, Pinaki Bhusan,Pradhan, Sourav,Punniyamurthy, Tharmalingam
, p. 10901 - 10910 (2019/09/13)
Aerobic copper(II)-catalyzed tandem ring opening and oxidative C-H alkylation of donor-acceptor cyclopropanes with bisaryl hydrazones is accomplished to produce tetrahydropyridazines, in which copper(II) plays dual role as a Lewis acid as well as redox catalyst. The reaction is stereospecific, and optically active cyclopropanes can be reacted with high optical purities (89-98% enantiomeric excess). The substrate scope, functional group tolerance, dual role of the copper(II) catalyst, and the use of air as an oxidant are the important practical features. A product bearing a 3-bromoaryl group can be subjected to Pd-catalyzed Suzuki coupling with boronic acid in high yield.
sp2-C–H Acetoxylation of Diversely Substituted (E)-1-(Arylmethylene)-2-phenylhydrazines Using PhI(OAc)2 as Acetoxy Source at Ambient Conditions
Brahmachari, Goutam,Karmakar, Indrajit
supporting information, p. 5925 - 5933 (2019/08/16)
A catalyst- and additive-free simple and straightforward method for regioselective direct sp2 C–H acetoxylation reaction of aldehyde hydrazones has been achieved at ambient temperature employing PIDA as an acetoxy source. The scope of the reaction has been successfully verified with a wide range of biologically important aldehyde hydrazones with diverse functional group tolerance. The method is highly selective, mild and efficient, operationally simple, rapid and high-yielding.
