61466-03-3Relevant academic research and scientific papers
Straightforward synthesis of diverse dipyrazolylmethane derivatives and their application for fluorescence sensing of Cu2+ ions
Kaliraj, Kaliappan,Xia, Likai,Edison, Thomas Nesakumar Jebakumar Immanuel,Lee, Yong Rok
, p. 56323 - 56329 (2016/07/06)
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.
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
Suzdalev, Konstantin F.,Babakova, Maria N.,Kartsev, Victor G.,Krasnov, Konstantin A.
, p. 64 - 75 (2015/05/12)
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.
The synthesis of dipyrazolylmethanes, x-ray structure analysis
Ma, Yuan,Wang, Jinxia,Ma, Hengchang
, p. 1645 - 1655 (2014/07/08)
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.
Friedlander synthesis of novel benzopyranopyridines in the presence of chitosan as heterogeneous, efficient and biodegradable catalyst under solvent-free conditions
Siddiqui, Zeba N.,Khan, Kulsum
, p. 1595 - 1602 (2013/05/21)
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.
Reactions of quinoxaline with 3-methyl-1-phenylpyrazol-5-one
Azev, Yurii A.,Oparina, Elena D.,Kovalev, Igor S.,Slepukhin, Pavel A.,Novikova, Rashida K.
experimental part, p. 37 - 38 (2012/05/04)
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.
New investigation of Vilsmeier-type reaction using pyrazolones with various amides
Huang, Yu-Ying,Kaneko, Kimiyoshi,Takayama, Hiroyuki,Kimura, Masayuki,Wong, Fung Fuh
supporting information; experimental part, p. 3786 - 3792 (2011/08/06)
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
Novel Vilsmeier-type methylenation for synthesis of dipyrazolylmethane derivatives using formamide or N-methylformamide
Wong, Fung Fuh,Huang, Yu-Ying
scheme or table, p. 3863 - 3867 (2011/06/21)
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.
Specific features of the reactions of quinazoline and its 4-hydroxy and 4-chloro substituted derivatives with C-nucleophiles
Azev, Yuri A.,Shorshnev, Sergey V.,Golomolzin, Boris V.
scheme or table, p. 2899 - 2903 (2009/09/08)
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-
