- Straightforward synthesis of diverse dipyrazolylmethane derivatives and their application for fluorescence sensing of Cu2+ ions
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A variety of dipyrazolylmethane derivatives were synthesized from the reactions of readily available β-keto esters with arylhydrazine hydrochlorides and DMF in the presence of p-toluenesulfonic acid (p-TsOH). This methodology provides a concise and practical one-pot route for the construction of diverse dipyrazolylmethane derivatives in good yield. As an application, the synthesized nitro-substituted compound displayed an excellent turn-off fluorescence sensing property for the detection of Cu2+ ions.
- Kaliraj, Kaliappan,Xia, Likai,Edison, Thomas Nesakumar Jebakumar Immanuel,Lee, Yong Rok
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p. 56323 - 56329
(2016/07/06)
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- Reaction of 2-chloro-1-alkyl-1H-indole-3-carbaldehydes with barbituric acids and 5-methyl-2-phenyl-2,4-dihydropyrazol-3-one. Formation of compound with extremely short intramolecular hydrogen bond in eight-membered pseudocycle
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New indolin-2-one derivatives, containing in its molecules eight-membered pseudo-cycle with unusually short intramolecular hydrogen bond in OHO-bridge have been synthesized by reaction of 2-chloro-1-alkyl-1H-indole-3-carbaldehyde with barbituric acids or 5-methyl-2-phenyl-2,4-dihydropyrazol-3-one. Under the action of amines they undergo fragmentation to 5-aminomethylenebarbituric acids or 4-aminomethylenepyrazolones and 1-alkyl-1,3-dihydroindol-2-ones.
- Suzdalev, Konstantin F.,Babakova, Maria N.,Kartsev, Victor G.,Krasnov, Konstantin A.
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- The synthesis of dipyrazolylmethanes, x-ray structure analysis
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A small dipyrazoylmethane compounds library was established via the reaction of 5-alkyl- and 5-aryl-2-aryl-3H-pyrazol-3-ones with DMSO in the presence of NaOAc 3H2O as base using LiBr H2O as additive at 100 oC.
- Ma, Yuan,Wang, Jinxia,Ma, Hengchang
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p. 1645 - 1655
(2014/07/08)
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- Friedlander synthesis of novel benzopyranopyridines in the presence of chitosan as heterogeneous, efficient and biodegradable catalyst under solvent-free conditions
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Efficient synthesis of benzopyrano[4,3-b]pyridine derivatives was achieved from 4-amino-3-formylcoumarin and different active methylene compounds under solvent-free thermal heating at 80 °C via Friedlander condensation in the presence of chitosan as heterogeneous, basic green catalyst. The present methodology is a novel green approach to benzopyranopyridine. It offers several advantages such as shorter reaction time, mild reaction conditions, simple operational procedure, use of recyclable and biodegradable catalyst.
- Siddiqui, Zeba N.,Khan, Kulsum
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p. 1595 - 1602
(2013/05/21)
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- Reactions of quinoxaline with 3-methyl-1-phenylpyrazol-5-one
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Quinoxaline during the reaction with 3-methyl-1-phenylpyrazol-5-one in the presence of triethylamine at room temperature in dimethylsulfoxide eliminates o-phenylenediamine and gives 4,4'-methylene-bis(3-methyl-1-phenylpyrazol-5-one) and 1,1,2,2-tetrakis(5-methyl-2-oxo-2-phenyl-1,2-dihydro-3H-pyrazol-4-yl)ethane. The latter was proved to be the intermediate to form the above dipyrazolylmethane derivative.
- Azev, Yurii A.,Oparina, Elena D.,Kovalev, Igor S.,Slepukhin, Pavel A.,Novikova, Rashida K.
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experimental part
p. 37 - 38
(2012/05/04)
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- New investigation of Vilsmeier-type reaction using pyrazolones with various amides
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New investigation of Vilsmeier-type reaction was evaluated to realize the solvent effect by using pyrazolones to react with various of amides, including formamide, N-methylformamide, N-propylformamide, N-tert-butylformamide, N,N-dimethylformamide (DMF), N,N-diethylformamide (DEF), N,N-dipropylformamide (DPF), N,N-diisopropylformamide, N,N-dibutylformamide, piperidine-1- carbaldehyde, and pyrrolidine-1-carbaldehyde, in the presence of phosphorous oxychloride POCl3. The unexpected resulting products were observed in this work according to the difference chemoseletivities of substituted amides. The plausible reactive pathways were proposed to explain the experimental result. Crown Copyright
- Huang, Yu-Ying,Kaneko, Kimiyoshi,Takayama, Hiroyuki,Kimura, Masayuki,Wong, Fung Fuh
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supporting information; experimental part
p. 3786 - 3792
(2011/08/06)
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- Novel Vilsmeier-type methylenation for synthesis of dipyrazolylmethane derivatives using formamide or N-methylformamide
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A novel Vilsmeier-type methylenation for synthesis of dipyrazolylmethanes was developed by reacting pyrazolones with formamide or N-methylformamide in the presence of phosphorous oxychloride POCl3 coupling agent. This method can efficiently provide a series of dipyrazolylmethane derivatives as the main products in excellent yields without the formylated products. Our experimental result was different with the classical Vilsmeier-type reaction.
- Wong, Fung Fuh,Huang, Yu-Ying
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scheme or table
p. 3863 - 3867
(2011/06/21)
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- Specific features of the reactions of quinazoline and its 4-hydroxy and 4-chloro substituted derivatives with C-nucleophiles
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Reactions of quinazoline 1 with indole, pyrogallol and 1-phenyl-3-methylpyrazol-5-one in the presence of acid led to C-4 adducts 2, 3 and 5. Adduct 4 is formed by heating 1 with 1,3-dimethylbarbituric acid without acid catalysis. 1-Phenyl-3-methylpyrazol-
- Azev, Yuri A.,Shorshnev, Sergey V.,Golomolzin, Boris V.
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scheme or table
p. 2899 - 2903
(2009/09/08)
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- 4-Bromo-3-methyl-1-phenylpyrazole in heterocyclic synthesis: Unexpected polysubstituted pyrazole derivatives
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Unexpected 4,4′-dipyrazolomethylidene (7), 4-amino-3a-bromo-3-methyl- 1-phenylpyrazolo[3,4-b]pyridin-6-thione (9), 4,4′-dipyrazolyl (18), ethyl 4-(3-methyl-1-phenylpyrazole-4-yl)fuoro[2,3-c]pyrazole-4-carboxylate (25), as well as the expected fuoro[2,3-c]pyrazole derivatives (15), (20) and (28) were isolated from a one-pot reaction of 4-bromo-3-methyl-1-phenylpyrazole (1) with some readily available reagents.
- El-Rady, Eman A.,Abd El Latif, Fawi M.
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p. 785 - 790
(2007/10/03)
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- Azines and their acyclic derivatives as transferers of one-carbon fragment in reactions with pyrazolones
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Enehydrazine derivatives have been obtained by the reaction of 6-phenyl-1,2,4-triazine 4-oxide with pyrazolones 2, which on further heating with pyrazolones 2 are converted into the corresponding symmetrical or unsymmetrical derivatives of dipyrazolylmethane. Enehydrazine derivatives of 1,3-dimethyl-5-nitrosouracil and 1,3-dimethylimidazolidine interact with 3-methyl-1-phenyl-5-pyrazolone (2a) with the formation of dipyrazolylmethane derivative. On interacting compound 2a or 3-methyl-1-(p-nitrophenyl)-5-pyrazolone with 3,6-diphenyl-1,2,4-triazine 4-oxide 12 the corresponding 4,4′-bispyrazolones are formed, but the interaction of compound 12 with 3-(p-nitrophenyl)-1-phenyl-5-pyrazolone leads to dipyrazolylmethane derivative. Dipyrazolylmethane derivative is obtained on heating of fervenulin 4-oxide, 2,4-dihydroxy-5-nitropyrimidine, and 1,3,5-triazines: 6-azauracil, 5-azauracil, azacytosine, and 2,4-diamino-s-triazine with pyrazolone 2a.
- Azev,Gryazeva,Golomolzin
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p. 1478 - 1486
(2007/10/03)
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- Phase transfer catalyzed C- Vs O- alkylation of 3-methyl-1-phenyl-2-pyrazolin-5-one in the absence or presence of carbon disulphide
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3-Methyl-l-phenyl-2-pyrazolin-5-one (1) was treated with different bromoorganic compounds such as benzyl bromide, 1,3-dibromo propane,methyl bromoacetate, bromoacetaldehyde diethylacetal as alkylating agents either in the absence or in the presence of carbon disulphide and under phase - transfer catalysis conditions aimed at studying the reactivity of the title compound with respect to C- vs O- alkylation.
- Hassan, Mohamed Ali,D?pp, Dietrich
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p. 451 - 465
(2007/10/03)
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- Attempted Niementowski condensation of anthranilic acid and its ester with 3-Methyl-1-phenylpyrazolin-5-one
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Two groups of compounds were formed in the attempted reaction of anthranilic acid and its ester with 3-methyl-1-phenylpyrazolin -5-one. The reactions of 3-methyl-1-phenylpyrazolin-5-one with aniline generated by decarboxylation of anthranilic acid constituted the first group of products. The second group of products comprised of pyrazole derivatives formed mainly by dimerization and dehydration of two molecules of 3-methyl-1-phenylpyrazolin-5-one.
- Danel,Tomasik,Kappe,Gheath
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p. 302 - 309
(2007/10/03)
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- About the Reaction of "Pyrazolone Blue" with Diazomethane
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The reaction of "pyrazolone blue" with diazomethane was investigated.A pyridazinone derivative 3, a heterocyclic spiro-cyclopropyl product 4 and a compound 7, which contains three pyrazolone and two diazomethane entities, are formed. 3 reacts with an exce
- Hennig, L.,Haessner, R.,Rissanen, K.
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p. 584 - 590
(2007/10/02)
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