- Three-Coordinate Zinc Methyl Complexes with Sterically Demanding Formazanate Ligands
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A series of heteroleptic three-coordinate mono(formazanate)zinc methyl complexes were synthesized, and the influence of the ligand on the structure as well as redox and optical properties of these complexes was investigated. The heteroleptic mono(formazan
- De Vries, Folkert,Travieso-Puente, Raquel,Roewen, Peter,Otten, Edwin
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- Sequential [3+2] annulation reaction of prop-2-ynylsulfonium salts and hydrazonyl chlorides: Synthesis of pyrazoles containing functional motifs
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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
- Jia, Tingting,Liu, Shourong,Shao, Jiaan,Shi, Tao,Wu, Zhaoxiao,Zeng, Linghui,Zhang, Chong,Zhang, Jiankang,Zhu, Huajian,Zhuang, Rangxiao
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p. 8460 - 8463
(2021/09/08)
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- 1,3-dipolar cycloaddition reactions of the compound obtaining from cyclopentadiene-PTAD and biological activities of adducts formed selectively
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After known adduct (4) was synthesized by cycloaddition reaction of cyclopentadiene with 4-phenyl-1,2,4-triazoline-3,5-dione, seven new isoxazoline derivatives were synthesized from reactions of 4 with corresponding oximes prepared from benzaldehyde derivatives in the existence of the aqueous NaOCl in CH2Cl2 at 0°C—RT via nitrile oxides. Four new pyrazoline derivatives were also synthesized from reactions of 4 with corresponding prepared reagents via nitrile imines. Selectively, each of all isoxazole and pyrazoline derivatives was synthesized by 1,3-dipolar cycloaddition reactions of compound 4 with the corresponding reagents. Based on the results of their biological activity analyses, Ki values for acetylcholinesterase (AChE), butyrylcholinesterase (BChE), and alpha-glucosidase (α-Gly) enzymes were obtained in this range 32.15 ± 5.73–107.44 ± 19.52 22.57 ± 4.30–186.07 ± 23.51, and 69.08 ± 8.54–528.07 ± 38.46 nM, respectively. Besides that, these compounds were subjected to molecular docking to describe the interaction against AChE, BChE, and α-Gly enzymes in which important interactions were visualized and evaluated with residues of the binding region in each target enzyme.
- Bayrak, Cetin,Menzek, Abdullah,Taskin-Tok, Tugba,Taslimi, Parham,Yavari, Mirali Akbar
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- Synthesis of 3 H-1,2,4-Triazol-3-ones via NiCl2-Promoted Cascade Annulation of Hydrazonoyl Chlorides and Sodium Cyanate
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A nickel-promoted cascade annulation reaction for the facile synthesis of 3H-1,2,4-triazol-3-ones from readily available hydrazonoyl chlorides and sodium cyanate has been developed. The transformation occurs through a cascade nickel-promoted intermolecular nucleophilic addition-elimination process, intramolecular nucleophilic addition, and a hydrogen-transfer sequence. The method has been successfully applied for the construction of the core skeleton of the angiotensin II antagonist.
- Du, Shiying,Yang, Zuguang,Tang, Jianhua,Chen, Zhengkai,Wu, Xiao-Feng
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p. 2359 - 2363
(2021/04/05)
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- Palladium-Catalyzed cascade carbonylative synthesis of 1,2,4-triazol-3-ones from hydrazonoyl chlorides and NaN3
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A palladium-catalyzed three-component carbonylative reaction for the synthesis of 3H-1,2,4-triazol-3-ones from hydrazonoyl chlorides and NaN3 has been achieved. The reaction presumably proceeds through a cascade carbonylation, acyl azide format
- Du, Shiying,Wang, Wei-Feng,Song, Yufei,Chen, Zhengkai,Wu, Xiao-Feng
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supporting information
p. 974 - 978
(2021/02/01)
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- Copper-Catalyzed Tandem Dehydrocyanation and [3+2] Cyclo-addition Reactions of Phenacylmalononitriles: Regioselective Synthesis of Functionalized 4-Benzoyl-5-cyanopyrazoles under Mild Conditions
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A novel copper-catalyzed [3+2] cycloaddition reaction with concomitant in situ generation of benzoylacrylonitriles and nitrile imines from phenacylmalononitriles and hydrazonoyl chlorides, respectively, is reported. The reaction was performed using copper(I) chloride as catalyst and N-methylimidazole as a clean complexing agent/weak base to afford the functionalized 4-benzoyl-5-cyanopyrazoles in moderate to good yields and excellent regioselectivity under ambient conditions. This method provides rapid access to a wide range of highly functionalized 4-benzoyl-5-cyanopyrazoles.
- Khaledian, Omid,Yavari, Issa
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p. 1379 - 1386
(2020/04/27)
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- A formal [3+2] cycloaddition reaction of: N -methylimidazole as a masked hydrogen cyanide: Access to 1,3-disubstitued-1 H -1,2,4-triazoles
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N-Methylimidazole (NMI) can act as a masked HCN in the synthesis of 1,3-disubstitued-1H-1,2,4-triazoles via a formal cycloaddition reaction of hydrazonoyl chloride with NMI. The product was proved to be formed via an initial nucleophilic substitution of hydrazonoyl chloride with NMI following cyclization and two sequential C-N bond cleavages. This journal is
- Yavari, Issa,Khaledian, Omid
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p. 9150 - 9153
(2020/10/02)
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- Facile One-Pot Transformation of Primary Alcohols into 3-Aryl- and 3-Alkyl-isoxazoles and -pyrazoles
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Various primary alcohols were smoothly transformed into 3-aryl- and 3-alkylisoxazoles in good yields in one pot by successive treatment with PhI(OAc) 2 in the presence of TEMPO, NH 2 OH, and then NCS, followed by reaction with alkynes in the presence of Et 3 N. Similarly, various primary alcohols were smoothly transformed into 3-aryl- and 3-alkylpyrazoles in good yields in one pot by successive treatment with PhI(OAc) 2 in the presence of TEMPO, PhNHNH 2, and then NCS and decyl methyl sulfide, followed by reaction with alkynes in the presence of Et 3 N. Thus, both 3-aryl- and 3-alkylisoxazoles, and 3-aryl- and 3-alkylpyrazoles could be prepared from readily available primary alcohols in one pot under transition-metal-free conditions.
- Kobayashi, Eiji,Togo, Hideo
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p. 3723 - 3735
(2019/09/30)
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- Synthesis, reactions, and antimicrobial activity of some novel pyrazolo[3,4-d]pyrimidine, pyrazolo[4,3-e][1,2,4]triazolo[1,5-c]pyrimidine, and pyrazolo[4,3-e][1,2,4]triazolo[3,4-c]pyrimidine derivatives
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Treatment of N-phenyl-substituted benzenecarbo-hydrazonoyl chlorides 1a-d with malononitrile in sodium ethoxide solution gave 5-amino-4-cyanopyrazole derivatives 2-5. Compounds 2-5 were converted to formidate derivatives 6-9 upon treatment with TEOF in ac
- Abdallah, Tayseer A.,Awad, Enas M.,Hassaneen, Hamdi M.,Mohamed, Yasmin Sh.,Saleh, Fatma M.
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- [3+2]-cycloaddition of in situ generated nitrile imines and acetylene for assembling of 1,3-disubstituted pyrazoles with quantitative deuterium labeling
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A novel synthetic methodology for the preparation of 1,3-disubstituted pyrazoles from in situ generated nitrile imines and acetylene is reported. The reactions are performed in a simple two-chamber reactor. One part of the reactor is loaded with hydrazonoyl chloride precursors of active nitrile imine species and a base. The other part is used to generate acetylene from CaC2 and water. Partitioning of the reactants improves the yields of desired pyrazoles up to 99% and simplifies their isolation to a simple procedure of solvent evaporation. The approach requires no complex equipment and utilizes inexpensive, safe, and easy to handle calcium carbide as a starting material. A model deuterium incorporation is carried out according to the developed methodology, producing a series of novel 4,5-dideuteropyrazoles with excellent deuterium enrichment. Theoretical calculations on reaction mechanism and characterization of possible intermediate structures were performed.
- Voronin, Vladimir V.,Ledovskaya, Maria S.,Gordeev, Evgeniy G.,Rodygin, Konstantin S.,Ananikov, Valentine P.
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p. 3819 - 3828
(2018/04/14)
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- A [4 + 3] Annulation Reaction of aza- o-Quinone Methides with Arylcarbohydrazonoyl Chlorides for Synthesis of 2,3-Dihydro-1 H-benzo[ e][1,2,4]triazepines
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An unprecedented [4 + 3] annulation reaction of aza-ortho-quinone methides with arylcarbohydrazonoyl chlorides has been achieved under mild conditions. The annulation underwent a sequential conjugate addition/intramolecular annulation/rearrangement, providing a useful method for the synthesis of biologically interesting 2,3-dihydro-1H-benzo[e][1,2,4]triazepine.
- Guo, Zhenyan,Jia, Hao,Liu, Honglei,Wang, Qijun,Huang, Jiaxing,Guo, Hongchao
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p. 2939 - 2943
(2018/05/28)
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- Synthesis of Spirobidihydropyrazole through Double 1,3-Dipolar Cycloaddition of Nitrilimines with Allenoates
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The double 1,3-dipolar cycloaddition of allenoates with nitrilimines has been achieved under mild reaction conditions, affording a variety of spirobidihydropyrazoles in moderate to excellent yields with excellent diastereoselectivities. The reaction diastereoselectively constructs double dihydropyrazole moieties and two chiral centers including a spiro carbon center.
- Liu, Honglei,Jia, Hao,Wang, Bo,Xiao, Yumei,Guo, Hongchao
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p. 4714 - 4717
(2017/09/23)
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- Exploiting the Electrophilic and Nucleophilic Dual Role of Nitrile Imines: One-Pot, Three-Component Synthesis of Furo[2,3-d]pyridazin-4(5H)-ones
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An expeditious multicomponent reaction to synthesize tetrasubstituted furo[2,3-d]pyridazin-4(5H)-ones is reported. In brief, hydrazonoyl chlorides react with isocyanoacetamides, in the presence of TEA, to give 1,3-oxazol-2-hydrazones which, without being isolated, can react with dimethylacetylene dicarboxylate to afford furo[2,3-d]pyridazin-4(5H)-ones with an unprecedented level of complexity in a triple domino Diels-Alder/retro-Diels-Alder/lactamization reaction sequence.
- Giustiniano, Mariateresa,Mercalli, Valentina,Amato, Jussara,Novellino, Ettore,Tron, Gian Cesare
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p. 3964 - 3967
(2015/09/01)
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- Synthesis of aminocarbonyl N-Acylhydrazones by a three-component reaction of isocyanides, hydrazonoyl chlorides, and carboxylic acids
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A novel one-pot multicomponent synthesis of α-aminocarbonyl N-acylhydrazones starting from readily available hydrazonoyl chlorides, isocyanides, and carboxylic acids is reported. The strategy exploits the ability of the carboxylic acid as a third component to suppress all competing reactions between nitrile imines and isocyanides, channeling the course of the reaction toward the formation of this novel class of compounds. (Chemical Equation Presented).
- Giustiniano, Mariateresa,Meneghetti, Fiorella,Mercalli, Valentina,Varese, Monica,Giustiniano, Francesco,Novellino, Ettore,Cesare Tron, Gian
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supporting information
p. 5332 - 5335
(2015/02/05)
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- An approach to pyrazoline-fused chlorins by dipolar [3 + 2]-cycloaddition of iminonitriles to Meso-Tetrakis(pentafluorophenyl)porphyrin: Synthesis of new PDT photosensitizers
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Meso-Tetrakis(pentafluorophenyl)porphyrin reacts at higher temperature with unstable iminonitriles (RC≡N+-N--Ar), affording pyrazoline-fused chlorins, according to dipolar [3 + 2]-cycloaddition pathway. The respective iminonitriles were in situ generated from the corresponding functionalized α-halogenohydrazine derivatives by 1,3-elimination of HX in the presence of base (NEt3, DABCO). This method allows synthesis of very attractive moieties which may be of potential use as sensitizers in photodynamic therapy (PDT).
- Wyrebek, Przemyslaw,Ostrowski, Stanislaw
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p. 1167 - 1174,8
(2020/09/16)
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- Synthesis, UV-Vis spectra, and Hammett correlation of some novel bis(dihydropyrrolo[3,4-c]pyrazoles)
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Twenty-nine novel bis(dihydropyrrolo[3,4-c]pyrazole) derivatives were obtained by reacting C, N-phenyl-substituted nitrilimines generated in situ from corresponding hydrazonyl chlorides with bismaleimides. The structures were elucidated by physical and spectroscopic methods [m.p., Rf, infrared (IR),1H nuclear magnetic resonance (NMR), 13C NMR, correlation spectroscopy (COSY), heteronuclear correlation (HETCOR), nuclear Overhauser effect (NOE), and high-resolution mass spectrometry (HRMS)]. Also, Hammett correlation graphs were obtained between Hammett constants σp and λmax values of bis(pyrrolopyrazoles) carrying p-substituted phenyl-ring-bearing electron-withdrawing and electrondonating groups and discussed in terms of substituent effects. Springer-Verlag 2010.
- Dueruest, Yasar,Yildirm, Muhammet
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scheme or table
p. 961 - 973
(2011/10/04)
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- Synthesis and antifungal activities of New pyrazole derivatives via 1,3-dipolar cycloaddition reaction
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A series of cycloadducts - pyrazoles via 1,3-dipolar cycloaddition reactions of generated nitrilimines with N-(4-chloro-2-fluorophenyl)maleimide were described. The novel compounds synthesized were characterized by 1H NMR, MS, and elemental analysis. The fungicidal tests showed that most of the title compounds exhibit significant fungicidal activities against Corynespora cassiicola.
- Zhang, Chuan-Yu,Liu, Xing-Hai,Wang, Bao-Lei,Wang, Su-Hua,Li, Zheng-Ming
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scheme or table
p. 489 - 493
(2011/02/21)
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- Structure-Activity Relationships in a Broad-Spectrum Anthelmintic Series. Acid Chloride Phenylhydrazones. 1. Aryl Substitutions and Chloride Variations
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The discovery of the broad-spectrum anthelmintic candidate p-toluoyl chloride phenylhydrazone was first reported in 1973.This account describes changes in anthelmintic activity with variations in substituents on the phenyl rings and modifications of the c
- Rector, Douglas L.,Folz, S. D.,Conklin, R. D.,Nowakowski, L. H.,Kaugars, Girts
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p. 532 - 538
(2007/10/02)
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- Method of use, composition, and compounds
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Certain benzoyl chloride phenylhydrazones have been found to be active against insects and mites. The benzoyl ring and the phenylhydrazone ring can be substituted with a halogen atom, a nitro group, or an alkyl group of from 1 to 6 carbon atoms, inclusive
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- Anthelmintic methods employing benzoyl chloride phenylhydrazones
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Certain benzoyl chloride phenylhydrazones have been found to be active against insects and mites, and they have also been found to be effective, broad-spectrum anthelmintics for suppressing parasitic worms in animals, particularly sheep. The benzoyl ring
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