- Facile synthesis of hydrazonyl halides by reaction of hydrazones with N-halosuccinimide-dimethyl sulfide complex
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A new and convenient method is described for the synthesis of hydrazonyl halides. Hydrazones on treatment with N-chlorosuccinimide-dimethyl sulfide complex result in the formation of the corresponding hydrazonyl chlorides in good yields. Similarly, treatment of hydrazones with N-bromosuccinimide-dimethyl sulfide complex gives the corresponding hydrazonyl bromide under extremely mild conditions.
- Patel, Himatkumar V.,Vyas, Kavita A.,Pandey, Sudhanshu P.,Fernandes, Peter S.
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- Synthesis of 1,3,3a,5-Tetraaryl-3a,4,5,6-tetrahydro-3H-1,2,4-triazolo[4,3-a][1,5]benzodiazepines
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A series of 3a,5-diaryl-1,3-diphenyl-3a,4,5,6-tetrahydro-3H-1,2,4-triazolo[4,3a][1,5]benzodiazepines was synthesized by the cycloaddition reactions of 2,4-diaryl-2,3-dihydro-1H-1,5-benzodiazepines and N-phenylbenzonitrileimine generated from N-phenylbenzenecarbohydrazonic chloride in the presence of triethylamine in anhydrous tetrahydrofuran.
- Xu, Jiaxi,Wang, Chenbo,Zhang, Qihan
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- Versatile approach to densely substituted isoxazolines and pyrazolines: Focus on a quaternary carbon center as a constitutive feature
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A new family of isoxazolines has been obtained via 1,3-dipolar cycloaddition in good to high yields under mild conditions. Our approach focused on construction of the heterocyclic ring and direct access to a quaternary carbon center at position 5. The met
- Abdelli, Abderrahmen,Gharsa, Haythem,Jma?, Momtez,Gaucher, Anne,Efrit, Mohamed Lotfi,M'rabet, Hedi,Prim, Damien
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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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- 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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- 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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- Controlled polymerization of styrene in the presence of Blatter’s radicals
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Controlled polymerization of styrene (both self-initiated and initiated with azobisisobutyronitrile) in the presence of Blatter’s radical at 125 °C was studied. When using the radical initiator, there is no induction period. On the basis of UV spectroscopy and MALDI massspectrometry studies, it was established that the Blatter radical is completely consumed at the initial stage of the polymerization, inserting into almost all macromolecules. The prepared polystyrene exhibits the ability to reinitialization in post-polymerization and the synthesis of block copolymers.
- Burdyukova, T. O.,Fedorov, A. Yu.,Grishin, I. D.,Kuznetsova, Yu. L.,Lopatin, M. A.,Malysheva, Yu. B.,Polozov, E. Yu.,Vavilova, A. S.,Zaburdaeva, E. A.
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p. 1470 - 1477
(2020/09/23)
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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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- From Phenylhydrazone to 1H-1,2,4-Triazoles via Nitrification, Reduction and Cyclization
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Herein we report an annulation of phenylhydrazone via a tandem nitrification, reduction, cyclization protocol employing cobalt nitrate and 1,2-dichloroethane to produce substituted 1H-1,2,4-triazoles. Notably, 1,2-dichloroethane serves both the solvent and a hydrogen source for transfer hydrogenation. This methodology works under mild conditions, providing a direct approach for the synthesis of 1H-1,2,4-triazoles. (Figure presented.).
- Hao, Liqiang,Wang, Guodong,Sun, Jian,Xu, Jun,Li, Hongshuang,Duan, Guiyun,Xia, Chengcai,Zhang, Pengfei
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p. 1657 - 1662
(2020/03/19)
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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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- Diversity Oriented Clicking (DOC): Divergent Synthesis of SuFExable Pharmacophores from 2-Substituted-Alkynyl-1-Sulfonyl Fluoride (SASF) Hubs
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Diversity Oriented Clicking (DOC) is a unified click-approach for the modular synthesis of lead-like structures through application of the wide family of click transformations. DOC evolved from the concept of achieving “diversity with ease”, by combining classic C?C π-bond click chemistry with recent developments in connective SuFEx-technologies. We showcase 2-Substituted-Alkynyl-1-Sulfonyl Fluorides (SASFs) as a new class of connective hub in concert with a diverse selection of click-cycloaddition processes. Through the selective DOC of SASFs with a range of dipoles and cyclic dienes, we report a diverse click-library of 173 unique functional molecules in minimal synthetic steps. The SuFExable library comprises 10 discrete heterocyclic core structures derived from 1,3- and 1,5-dipoles; while reaction with cyclic dienes yields several three-dimensional bicyclic Diels–Alder adducts. Growing the library to 278 discrete compounds through late-stage modification was made possible through SuFEx click derivatization of the pendant sulfonyl fluoride group in 96 well-plates—demonstrating the versatility of the DOC approach for the rapid synthesis of diverse functional structures. Screening for function against MRSA (USA300) revealed several lead hits with improved activity over methicillin.
- Barrow, Andrew S.,Cheng, Yunfei,Gialelis, Timothy L.,Giel, Marie-Claire,Kitamura, Seiya,Li, Gencheng,Moses, John E.,Ottonello, Alessandra,Sharpless, K. Barry,Smedley, Christopher J.,Wolan, Dennis W.
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p. 12460 - 12469
(2020/06/10)
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- Transition-Metal-Free Coupling of 1,3-Dipoles and Boronic Acids as a Sustainable Approach to C?C Bond Formation
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The need for alternative, complementary approaches to enable C?C bond formation within organic chemistry is an on-going challenge in the area. Of particular relevance are transformations that proceed in the absence of transition-metal reagents. In the current study, we report a comprehensive investigation of the coupling of nitrile imines and aryl boronic acids as an approach towards sustainable C?C bond formation. In situ generation of the highly reactive 1,3-dipole facilitates a Petasis–Mannich-type coupling via a nucleophilic boronate complex. The introduction of hydrazonyl chlorides as a complementary nitrile imine source to the 2,5-tetrazoles previously reported by our laboratory further broadens the scope of the approach. Additionally, we exemplify for the first time the extension of this protocol into another 1,3-dipole, through the synthesis of aryl ketone oximes from aryl boronic acids and nitrile N-oxides.
- Livingstone, Keith,Bertrand, Sophie,Kennedy, Alan R.,Jamieson, Craig
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p. 10591 - 10597
(2020/07/25)
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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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- Intramolecular Diels-Alder and [3+2] Cycloaddition Reactions in the One-Pot Synthesis of Epoxypyrrolo[3,4-g]indazoles
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A one-pot approach for the synthesis of epoxypyrrolo[3,4- g ]indazoles is presented. The first step was initiated by a three-component reaction of an isocyanide, a dialkyl acetylenedicarboxylate, and 2-furancarboxylic acid, and led to 1,3-dioxoepoxyisoindole, followed by the addition of hydrazonoyl chloride through a [3+2]-cycloaddition reaction in the second step. The key step in the formation of final compound involves a bicyclization strategy through intramolecular Diels-Alder (IMDA) reaction.
- Alizadeh, Abdolali,Amir Ashjaee Asalemi, Kaveh,Halvagar, Mohammadreza
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p. 2936 - 2944
(2019/07/22)
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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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- Spirotriazoline oxindoles: A novel chemical scaffold with in vitro anticancer properties
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The design and synthesis of a library of twenty-six spirotriazoline oxindoles and their in vitro evaluation as potential anticancer agents is reported. The antiproliferative activity of the synthesized compounds was assessed against four different cancer cell lines (HCT-116 p53 (+/+), HCT-116 p53 (?/?), MCF-7, and MDA-MB-231). Four spirotriazoline oxindoles showed selectivity against the four cancer cell lines tested over the non-cancer derived HEK 293T cell line. To characterize the molecular mechanisms involved in compound antitumoral activity, two spirotriazoline oxindoles were selected for further studies. Both compounds were able to induce apoptosis and cell cycle arrest at G0/G1 phase and upregulated p53 steady-state levels, while decreasing its main inhibitor MDM2, in HCT-116 cells. Importantly, cytotoxic effects induced by spirotriazoline oxindoles occurred in cancer cells without eliciting cell death in non-malignant CCD-18Co human colon fibroblasts. In addition, four spirotriazoline oxindoles showed selectivity against the triple-negative breast cancer cell line MDA-MB-231 with IC50 values of 3.5–6.7 μM. These results highlight the anticancer potential of spirotriazoline oxindoles, especially when dealing with aggressive and challenging triple-negative breast cancer.
- Ribeiro, Carlos J.A.,Nunes, Rute C.,Amaral, Joana D.,Gon?alves, Lídia M.,Rodrigues, Cecília M.P.,Moreira, Rui,Santos, Maria M.M.
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p. 494 - 509
(2017/10/10)
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- A Convenient 1,3-Dipolar Cycloaddition Reaction for the Synthesis of Spirooxindoles and Some Other Spirocompounds Containing the 1,3,4-Oxadiazole Moiety
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A series of spiro[indoline-3,2′-[1,3,4]oxadiazol]-2-ones were prepared from the reaction of isatin derivatives and hydrazonoyl chlorides through the 1,3-dipolar cycloaddition reaction. This method has some important aspects, such as mild reaction condition, easy purification, and high yield of products. Also, the synthesis of spiro[acenaphthylene-1,2′-[1,3,4]oxadiazol]-2-one and spiro[[1,3,4]oxadiazole-2,9′-phenanthren]-10′-one were studied under the same condition. The structures were confirmed spectroscopically (IR,1H- and13C-NMR, and EI-MS) and by elemental analyses. A plausible mechanism for this reaction is proposed.
- Alizadeh, Abdolali,Moafi, Leila
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p. 457 - 461
(2016/07/06)
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- 1,4-Bis-Dipp/Mes-1,2,4-Triazolylidenes: Carbene Catalysts That Efficiently Overcome Steric Hindrance in the Redox Esterification of α- And β-Substituted α,β-Enals
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As reported by Scheidt and Bode in 2005, sterically nonencumbered α,β-enals are readily converted to saturated esters in the presence of alcohols and N-heterocyclic carbene catalysts, e.g., benzimidazolylidenes or triazolylidenes. However, substituents at the α- or β-position of the α,β-enal substrate are typically not tolerated, thus severely limiting the substrate spectrum. On the basis of our earlier mechanistic studies, a set of N-Mes- or N-Dipp-substituted 1,2,4-triazolium salts were synthesized and evaluated as (pre)catalysts in the redox esterification of various α- or β-substituted enals. In particular the 1,4-bis-Mes/Dipp-1,2,4-triazolylidenes overcome the above limitations and efficiently catalyze the redox esterification of a whole series of α/β-substituted enals hitherto not amenable to NHC-catalyzed transformations. The synthetic value of 1,4-bis-Mes/Dipp-1,2,4-triazolylidenes is further demonstrated by the one-step bicyclization of 10-oxocitral to (racemic) nepetalactone in diastereomerically pure form.
- Yatham, Veera Reddy,Harnying, Wacharee,Kootz, Darius,Neud?rfl, J?rg-M.,Schl?rer, Nils E.,Berkessel, Albrecht
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p. 2670 - 2677
(2016/03/12)
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- Synthesis of novel spiropyrazoline oxindoles and evaluation of cytotoxicity in cancer cell lines
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A series of novel spiropyrazoline oxindole derivatives was synthesized by 1,3-dipolar cycloaddition reaction. The compounds were screened for their in vitro cytotoxic activity against MCF-7 breast cancer cell line (estrogen receptor positive (ER+) and hum
- Monteiro, ?ngelo,Gon?alves, Lídia M.,Santos, Maria M.M.
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p. 266 - 272
(2014/05/06)
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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 and stereochemistry of some novel dihydropyrrolo[3,4-c]pyrazoles
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Eleven novel dihydropyrrolo[3,4-c]pyrazole derivatives were obtained by the reaction of chiral (1R)-N-(1-phenylethyl)maleimide and C,N-aryl-substituted nitril-imines. The reaction afforded the cycloadducts as a regioisomeric mixture which can be separable in some cases. The structure and stereochemistry of cycloadducts were assigned on the basis of infrared (IR), 1H and 13C nuclear magnetic resonance (NMR), mass and X-ray spectra, optical rotation measurements, and CHN analyses.
- Dueruest, Yasar,Yildirm, Muhammet,Fronczek, Chris F.,Fronczek, Frank R.
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p. 127 - 138
(2012/07/27)
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- Ruthenium complexes incorporating azoimine and α-diamine based ligands: Synthesis, crystal structure, electrochemistry and DFT calculation
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Ru(II) complexes, trans-[RuCl2(Azo)L] [where Azo = C 6H5NNC(C6H5)NC6H 5, L = 2,2′-bipyridine (bpy) (C1), 4,4′-dimethyl-2, 2′-bipyridine (dmb) (C2), 1,10-phenanthroline (phen) (C3
- Al-Noaimi, Mousa,Aldamen, Murad A.
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body text
p. 45 - 51
(2012/06/30)
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- Synthesis of new thienopyridine derivatives by [3+2]- and [2+2]-cycloaddition reactions
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The reaction of 6,7-dihydrothieno[3,2-c]pyridine derivatives with 1,3-dipoles, such as a nitrile oxides or nitrile imines, gave novel fused heterocycles. The Staudinger reaction of the starting material was also studied. This reaction was stereoselective
- Milen, Matyas,Abranyi-Balogh, Peter,Keglevich, Gyoergy,Dancso, Andras
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p. 3447 - 3452,6
(2012/12/13)
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- Design and synthesis of 1,3,5-trisubstituted 1,2,4-triazoles as CYP enzyme inhibitors
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A series of 1,3,5-trisubstituted 1,2,4-triazoles was designed and synthesized as potential inhibitors of ste-roidogenic CYP enzymes. The 1,2,4-triazole is part of the core structure fixing the geometry of the substances. A pyridine moiety was introduced as heme-binder. The target compounds were synthesized in two to four steps using silver carbonate mediated ring closure and Suzuki cross coupling reaction as key synthetic transformations. Biological testing of the synthesized compounds for the inhibition of the most important steroidogenic CYPs revealed compounds 29a and 30 as moderate inhibitors of aldo-sterone synthase (CYP11B2).
- Al-Soud, Yaseen A.,Heydel, Michael,Hartmann, Rolf W.
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p. 6372 - 6375
(2012/01/02)
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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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experimental part
p. 489 - 493
(2011/02/21)
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- 1,3-Dipolar Cycloadditions of 2-Ethoxy- and 2-(Ethylthio)-1-azetines with Nitrile Oxides, Nitrile Ylides and Nitrilimines: An Unexpected 1,2,4-Triazole Formation.
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2-Ethoxy- and 2-(ethylthio)-1-azetines readily undergo 1,3-dipolar cycloadditions with nitrile oxides and nitrile ylides to give stable 4,5-bicyclic cycloadducts.With nitrilimines, however, the expected 1,3-dipolar cycloadducts and/or unexpected ring-open
- Hemming, Karl,Luheshi, Abdul-Bassett N.,Redhouse, Alan D.,Smalley, Robert K.,Thompson, J. Robin,et al.
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p. 4383 - 4408
(2007/10/02)
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- Inhibiteurs mixtes des voies de la cyclooxygenase et des lipoxygenases: synthese et activite de derives hydrazoniques
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Dual inhibitors of the cyclooxygenase and lipoxygenase pathways: synthesis and activity of hydrazone derivatives.Non-steroidal anti-inflammatory drugs (NSAIDs) act by preventing prostaglandin production.In recent years, research on non-steroid dual inhibitors of prostaglandin and leukotriene biosyntheses has been developed.These compounds should represent a new class of anti-inflammatory drugs, with a wider spectrum of activity than classical NSAIDs.The present paper reports the synthesis of hydrazone derivatives.The effect of various substitutions is studied on platelet cyclooxygenase (i.e. prostaglandin synthesis) and on leukocyte 5-lipoxygenase (i.e. leukotriene synthesis).Among the 50 tested compounds, 2 hydrazone derivatives were selected for their significant dual inhibitory potency: 2-acetylthiophene-2-thiazolylhydrazone 5g, and N-phenyl benzimidrazone 6c.Keywords - non-steroidal anti-inflammatory drugs / hydrazones / dual inhibitor / cyclooxygenase / lipoxygenase
- Ghiglieri-Bertez, Chantal,Coquelet, Claude,Alazet, Alain,Bonne, Claude
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p. 147 - 152
(2007/10/02)
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- Effect of metal ions in organic synthesis. Part XV. Reaction of (arylazo) alkenes and copper(II) chloride in dienophiles or acetone. Synthesis of some N-(α-chlorobenzylidene)-N'-arylhydrazines
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The reaction of (phenylazo) stilbene and copper(II) chloride with some dienophiles produced benzaldehyde and N-(α-chlorobenzylidene)-N'-phenylhydrazine, instead of the expected (4+2)-cycloaddition products.By reaction of some (arylazo) alkenes and copper(
- Attanasi, Orazio,Battistoni, Paolo,Fava, Gabriele
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p. 2665 - 2668
(2007/10/02)
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