- Enolization versus carbonylation at glassy carbon surface through cathodic means
-
The cathodic reduction of ω-bromomethylarylketones in aprotic organic solvents (such as propylene carbonate) containing tetraalkylammonium iodides achieved at smooth glassy carbon (GC) permits through a selective one-electron reduction, the scission of th
- Simonet, Jacques
-
-
Read Online
- Visible-Light-Triggered Iodinations Facilitated by Weak Electrostatic Interaction of N-Heterocyclic Carbenes
-
N-heterocyclic carbenes (NHCs) are well-known as ligands and organocatalysts, but there is no recognition for their catalytic role as a stabilizer through electrostatic interaction rather than electron donation. By utilizing the electrostatic interaction, we herein describe the success of a visible-light-triggered radical-radical cross-coupling of N-alkenoxypyridinium salts and NaI, giving a variety of α-iodo ketones. Computational studies characterize the stabilization role of NHCs.
- Chen, Xiang-Yu,Liu, Qiang,Lu, Yu,Sheng, He,Su, Xiao-Di,Wang, Zhi-Xiang
-
supporting information
p. 7187 - 7192
(2020/10/02)
-
- Au(I)-Catalyzed Hydration of 1-Iodoalkynes Leading to α-Iodoketones
-
A catalytic protocol for the Au(I)-catalyzed hydration of 1-iodoalkynes is disclosed. The use of Au(I)–NHC catalyst enabled the straightforward synthesis of a variety of α-iodomethyl ketones in good to excellent yields. The utility of this simple method is further highlighted by showcasing iodination/hydration and hydration/oxidation sequential protocols leading to the construction of molecular complexity.
- Cazin, Catherine S. J.,Gómez-Herrera, Alberto,Hashim, Ishfaq Ibni,Nahra, Fady,Porré, Marre
-
supporting information
p. 6790 - 6794
(2020/11/23)
-
- Imidazolium-Based Ionic Network as a Robust Heterogeneous Catalyst in Synthesis of Phenacyl Derivatives
-
A new imidazolium-based poly(ionic liquid) has been synthesized and used as a robust heterogeneous catalyst for the preparation of phenacyl derivatives by an SN2 reaction of different phenacyl bromides with a broad range of nucleophiles. The products are obtained in high yields under mild conditions. The catalyst can be recycled efficiently.
- Kakesh,Sayyahi,Badri,Tahanpesar
-
p. 1218 - 1220
(2019/07/16)
-
- Synthesis of Isoxazolines and Isoxazoles via Metal-Free Desulfitative Cyclization
-
A novel, one-pot reaction for the synthesis of isoxazolines and isoxazoles is developed via a cascade process under metal-free conditions. The approach involves the formation of intramolecular C-N and C-O bonds and intermolecular C-C bonds from aromatic alkenes or alkynes and N -hydroxysulfonamides using hypervalent iodine(VII) and iodine as the oxidant. Activation of C-H and C-C bonds/construction of C-O bonds/elimination of SO 2 /C-N bond formation is achieved in sequence in the reaction system.
- Cheng, Jiaxin,Yang, Ze,Li, Yuansheng,Xi, Yulan,Sun, Qiu,He, Ling
-
p. 2385 - 2393
(2018/05/28)
-
- Metal-Free, Oxidant-Free, and Controllable Graphene Oxide Catalyzed Direct Iodination of Arenes and Ketones
-
A direct, metal-free, and oxidant-free method for the graphene oxide (GO)-catalyzed iodination of arenes and ketones with iodine in a neutral medium was explored. This iodination protocol was performed by using a simple technique to avoid the use of external metal catalysts and oxidants and harsh acidic/basic reaction conditions. In addition, by this method the degree of iodination could be controlled, and the reaction was scalable and compatible with air. This strategy opens a new field for GO-catalyzed chemistry and provides an avenue for the convenient direct iodination of arenes and ketones.
- Zhang, Jingyu,Li, Shiguang,Deng, Guo-Jun,Gong, Hang
-
p. 376 - 380
(2017/12/07)
-
- An AKAP-Lbc-RhoA interaction inhibitor promotes the translocation of aquaporin-2 to the plasma membrane of renal collecting duct principal cells
-
Stimulation of renal collecting duct principal cells with antidiuretic hormone (arginine-vasopressin, AVP) results in inhibition of the small GTPase RhoA and the enrichment of the water channel aquaporin-2 (AQP2) in the plasma membrane. The membrane inser
- Schrade, Katharina,Tr?ger, Jessica,Eldahshan, Adeeb,Zühlke, Kerstin,Abdul Azeez, Kamal R.,Elkins, Jonathan M.,Neuenschwander, Martin,Oder, Andreas,Elkewedi, Mohamed,Jaksch, Sarah,Andrae, Karsten,Li, Jinliang,Fernandes, Joao,Müller, Paul Markus,Grunwald, Stephan,Marino, Stephen F.,Vuki?evi?, Tanja,Eichhorst, Jenny,Wiesner, Burkhard,Weber, Marcus,Kapiloff, Michael,Rocks, Oliver,Daumke, Oliver,Wieland, Thomas,Knapp, Stefan,Von Kries, Jens Peter,Klussmann, Enno
-
-
- Rapid and efficient one-pot microwave-assisted synthesis of 2-phenylimidazo[1,2-a]pyridines and 2-phenylimidazo[1,2-a]quinoline in water–PEG-400
-
An effective, expeditious, environmentally benign one-pot synthesis of 2-phenylimidazo[1,2-a]pyridines and 2-phenylimidazo[1,2-a]quinoline from easily available starting materials as aromatic carbonyl compound, 2-amino pyridine, succinamide, and in situ g
- Jadhav, Santosh A.,Shioorkar, Mahesh G.,Chavan, Omprakash S.,Sarkate, Aniket P.,Shinde, Devanand B.
-
supporting information
p. 285 - 290
(2017/02/10)
-
- Mild and General Synthesis of Pyrrolo[2,1-a]isoquinolines and Related Polyheterocyclic Frameworks from Pyrrole Precursors Derived from a Mechanochemical Multicomponent Reaction
-
The combination of a three-component, solvent-free pyrrole synthesis performed under mechanochemical conditions with a TMSOTf-catalyzed oxonium-mediated cyclization gave general access to pyrrolo[2,1-a]isoquinoline derivatives under very mild conditions.
- Leonardi, Marco,Villacampa, Mercedes,Menéndez, J. Carlos
-
p. 2570 - 2578
(2017/03/14)
-
- Expeditious one-pot multicomponent microwave-assisted green synthesis of substituted 2-phenyl Quinoxaline and 7-bromo-3-(4-ethylphenyl) pyrido[2,3-b]pyrazine in water–PEG and water–ethanol
-
An eco-friendly, expeditious one-pot multicomponent synthesis of substituted 2-phenyl quinoxaline and 7-bromo-3-(4-ethylphenyl) pyrido[2,3-b]pyrazine 4a–k in water–ethanol from easily available starting materials as acetophenone 1, succinamide 2, aromatic
- Jadhav, Santosh A.,Sarkate, Aniket P.,Shioorkar, Mahesh G.,Shinde, Devanand B.
-
p. 1661 - 1667
(2017/09/08)
-
- Metal-free hydration of aromatic haloalkynes to α-halomethyl ketones
-
A highly regioselective and efficient metal-free hydration of aromatic haloalkynes to α-halomethyl ketones using cheap tetrafluoroboric acid as catalyst is described. The protocol is conducted under convenient conditions and affords products in good to excellent yields, with broad substrate scope, including a variety of aromatic alkynyl chlorides, alkynyl bromides, and alkynyl iodides.
- Ye, Min,Wen, Yuelu,Li, Huifang,Fu, Yejuan,Wang, Qinghao
-
supporting information
p. 4983 - 4986
(2016/10/21)
-
- Integration of aqueous biphasic with magnetically recyclable systems: Polyethylene glycol-grafted Fe3O4 nanoparticles catalyzed phenacyl synthesis in water
-
The present work trends to define an efficient phenacyl catalytic synthesis method employing a new nano-magnetite-supported organocatalyst. Polyethylene glycol (PEG) was bonded successfully onto silica coated ferrite and the resultant nanoparticles (PEG@SiO2@Fe3O4) characterized by fourier transform infrared spectroscopy (FT-IR), atomic force microscopy (AFM), thermal gravimetric analysis (TGA), vibrating sample magnetometry (VSM), energy dispersive X-ray analysis (EDAX) and X-ray diffraction (XRD) that exhibited a good catalytic activity in the reaction. The nanoparticles could be easily separated from the reaction mixture by an external magnet and reused in seven reaction cycles without significant loss of activity.
- Amini, Atefeh,Sayyahi, Soheil,Saghanezhad, Seyyed Jafar,Taheri, Narges
-
-
- A simple method for the synthesis of furfuryl ketones and furylacetic acid derivatives
-
A simple preparative method has been developed for the synthesis of aryl(furfuryl) ketones, amides, and furylacetic acid esters, based on radical alkylation of furan derivatives at the α-position with O-ethyl(phenacyl)xanthogenates and phenacyl iodides in the presence of Fenton's reagent (H2O2/FeSO4·7H2O) in DMSO. The range of applicability and mechanisms for the formation of major and side products have been considered.
- Chalikidi, Petrakis N.,Nevolina, Tatyana A.,Uchuskin, Maxim G.,Abaev, Vladimir T.,Butin, Alexander V.
-
p. 621 - 629
(2015/10/12)
-
- Direct one-pot synthesis of zolimidine pharmaceutical drug and imidazo[1,2-a]pyridine derivatives via I2/CuO-promoted tandem strategy
-
An efficient one-pot synthetic protocol was developed for the synthesis of imidazo[1,2-a]pyridines from easily available starting materials: Aromatic ketones, α,β-unsaturated ketones, β-keto esters and 2-aminopyridines. The present reaction proceeded well in MeOH under the media of I2/CuO. By using this method, the marketed drug zolimidine could be prepared easily with 95% yield. All these target products were characterized by NMR, HRMS and IR spectra. Furthermore, the target compound 3fa was determined by X-ray crystallographic analysis.
- Cai, Qun,Liu, Mei-Cai,Mao, Bi-Ming,Xie, Xuan,Jia, Feng-Cheng,Zhu, Yan-Ping,Wu, An-Xin
-
p. 881 - 884
(2015/03/04)
-
- Metal-free in situ sp3, sp2, and sp C-H functionalization and oxidative cross coupling with benzamidines hydrochloride: A promising approach for the synthesis of α-ketoimides
-
A new metal-free tandem protocol for the synthesis of α-ketoimides via sp3, sp2, and sp C-H functionalization followed by oxidative cross coupling with benzamidines hydrochloride using catalytic iodine with TBHP in DMSO has been developed. A wide range of functional group tolerance, an inexpensive catalyst, operational simplicity and good to excellent yields of the products are the striking features of this method.
- Kalmode, Hanuman P.,Vadagaonkar, Kamlesh S.,Chaskar, Atul C.
-
p. 60316 - 60326
(2015/02/19)
-
- The α-chlorination of aryl methyl ketones under aerobic oxidative conditions
-
The novel reaction system air/ammonium nitrate/iodine/hydrochloric acid [air/NH4NO3(cat.)/I2(cat.)/HCl] is introduced as a simple, safe, cheap, efficient and regioselective mediator for the α-chlorination of aryl, heteroaryl and alkyl methyl ketones under aerobic oxidative conditions. The inventive use of a catalytic amount of iodine enabled the moderate to quantitative, regioselective chlorination of a comprehensive scope of different methyl ketone derivatives including those bearing oxidizable heteroatom (S, N) substituents, some of which possess declared potential biological and pharmaceutical activity. Air oxygen under a slight overpressure plays the role of the terminal oxidant catalytically activated by redox cycles of nitrogen oxides released from the catalytic amount of ammonium nitrate (NH4NO3) under acidic conditions of hydrochloric acid (HCl) and co-catalyzed by elemental iodine (I2), which was found to be essential for the high efficiency of the reaction system.
- Prebil, Rok,Stavber, Stojan
-
supporting information
p. 1266 - 1274
(2014/05/06)
-
- Aerobic oxidative α-iodination of carbonyl compounds using molecular iodine activated by a nitrate-based catalytic system
-
The novel reaction system comprising air/NH4NO3(cat.)/I2/H2SO4(cat.)is introduced as a simple, safe, cheap, efficient, and regioselective mediator for direct aerobic oxidative α-iodination of aryl, heteroaryl, alkyl, and cycloalkyl methyl ketones. The reaction system enabled the moderate to quantitative regioselective iodination of a large range of different methyl ketone derivatives including those bearing oxidizable heteroatom (S, N) substituents. Several activated aromatic compounds were also efficiently and selectively iodinated. The practical applicability of the presented reaction system was shown on 20 mmol scale under ambient pressure and 100% conversion of substrate was achieved.
- Prebil, Rok,Stavber, Stojan
-
supporting information
p. 5643 - 5647
(2014/12/11)
-
- Synthesis of α-iodoketals from methyl ketones via sustainable and orthogonal tandem catalysis
-
A highly efficient method for the direct synthesis of α-iodoketals from methyl ketones has been developed via sustainable integration of orthogonal tandem catalytic reactions: copper(ii) oxide catalyzed iodination reaction and the subsequent excess or reg
- Yang, Yan,Gao, Meng,Shu, Wen-Ming,Wu, Liu-Ming,Zhang, Dong-Xue,Wu, An-Xin
-
p. 1226 - 1233
(2013/03/29)
-
- Bronsted acidic ionic liquid accelerated halogenation of organic compounds with N-halosuccinimides (NXS)
-
The Bronsted-Acidic ionic liquid 1-methyl-3-(4-sulfobutyl) imidazolium triflate [BMIM(SO3H)][OTf] was demonstrated to act efficiently as solvent and catalyst for the halogenation of activated organic compounds with N-halosuccinimides (NXS) under mild conditions with short reaction times. Methyl aryl ketones were converted into a-halo and a,a-dihaloketones, depending on the quantity of NXS used. Ketones with activated aromatic rings were selectively halogenated, however in some cases mixtures of a-halogenated ketone and ring-halogenated ketones were obtained. Activated aromatics were regioselectively ring halogenated to give mono- and dihalo-substituted products. The [BMIM(SO3H)][OTf] ionic liquid (IL-A) was successfully reused eight times in a representative monohalogenation reaction with no noticeable decrease in efficiency. An effective halogenation scale-up in this IL is also presented. The reactivity trend and the observed chemo- and regioselectiivities point to an ET process in these IL-promoted halofunctionalization reactions.
- Vrazic, Dejan,Jereb, Marjan,Laali, Kenneth K.,Stavber, Stojan
-
-
- Design and synthesis of 2-acylbenzothiazoles via in situ cross-trapping strategy from benzothiazoles with aryl ketones
-
An I2/KOH synergistically promoted direct ring-opening aroylation of benzothiazoles with aryl ketones has been discovered. Aryl ketones were seen to act as carbonyl sources to construct 2-acylbenzothiazoles. This reaction could provide an example for the convergent integration of self-labor domino sequences based on an in situ cross-trapping strategy.
- Gao, Qinghe,Wu, Xia,Jia, Fengcheng,Liu, Meicai,Zhu, Yanping,Cai, Qun,Wu, Anxin
-
p. 2792 - 2797
(2013/04/24)
-
- A direct method for the synthesis of indolizine derivatives from easily available aromatic ketones, pyridines, and acrylonitrile derivatives
-
A concise and efficient strategy has been proposed to synthesize indolizine derivatives from easily available aryl or heteroaryl methyl ketones, pyridines, and acrylonitriles. The mechanistic pathway involved the integration of iodination, pyridinium ylid
- Cai, Qun,Zhu, Yan-Ping,Gao, Yang,Sun, Jing-Jing,Wu, An-Xin
-
supporting information
p. 414 - 419
(2013/07/25)
-
- Target-oriented synthesis: Miscellaneous synthetic routes to access 1,4-enediones through the coupling of 1,3-dicarbonyl compounds with multiform substrates
-
Target-oriented synthetic protocol was presented for the synthesis of 1,4-enediones. The approach can efficiently construct 1,4-enediones through different reaction pathways from multiform substrates α-halo aromatic ketones, 2-hydroxy-aromatic ketones and methyl carbinols. In this reaction, CuI was found to be the most efficient catalyst. Multiform substrates were also found to perform well to afford the products in a one-pot fashion.
- Zhu, Yan-Ping,Cai, Qun,Gao, Qing-He,Jia, Feng-Cheng,Liu, Mei-Cai,Gao, Meng,Wu, An-Xin
-
supporting information
p. 6392 - 6398
(2013/07/25)
-
- Direct preparation of thiazoles, imidazoles, imidazopyridines and thiazolidines from alkenes
-
A range of heterocycles, namely thiazoles, imidazoles, imidazopyridines, thiazolidines and dimethoxyindoles, have been synthesised directly from alkenes via a two-step ketoidoination/cyclisation protocol. The alkene starting materials are themselves readily accessible using many different and well-established approaches, and allow access to a variety of heterocycles with excellent yields and regioselectivity.
- Donohoe, Timothy J.,Kabeshov, Mikhail A.,Rathi, Akshat H.,Smith, Ian E. D.
-
experimental part
p. 1093 - 1101
(2012/04/04)
-
- IBX/Imediated reaction of sodium arenesulfinates with alkenes: Facile synthesis of β-keto sulfones
-
A direct synthesis of -keto sulfones from alkenes is described. A combination of o-iodoxybenzoic acid/iodine (IBX/I was found to mediate the reactions of alkenes with arenesulfinates to yield -keto sulfones in good yields via a one-pot reaction. Georg Thieme Verlag Stuttgart · New York.
- Samakkanad, Natthapol,Katrun, Praewpan,Techajaroonjit, Thanachart,Hlekhlai, Sornsiri,Pohmakotr, Manat,Reutrakul, Vichai,Jaipetch, Thaworn,Soorukram, Darunee,Kuhakarn, Chutima
-
experimental part
p. 1693 - 1699
(2012/07/03)
-
- A multipathway coupled domino strategy: Metal-free oxidative cyclization for one-pot synthesis of 2-acylbenzothiazoles from multiform substrates
-
A multipathway coupled domino strategy has been developed for the efficient synthesis of 2-acylbenzothiazoles from multiform substrates arylethenes, arylacetylenes, 2-hydroxy-aromatic ketones, and carbinols via four distinct pathways. Through a logical coupled oxidation/heterocyclization domino process, a variety of 2-acylbenzothiazoles were synthesized free of metal in one pot.
- Zhu, Yan-Ping,Jia, Feng-Cheng,Liu, Mei-Cai,Wu, An-Xin
-
supporting information
p. 4414 - 4417
(2012/10/29)
-
- Catalytic electrophilic halogenation of silyl-protected and terminal alkynes: Trapping gold(I) acetylides vs. a Bronsted acid-promoted reaction
-
In the presence of a cationic gold(I) catalyst and N-halosuccinimide, both trimethylsilyl-protected and terminal alkynes are converted into alkynyl halides. Further experiments showed that silyl-protected alkynes undergo electrophilic iodination and bromination under Bronsted acid catalysis, whilst terminal alkynes require a cationic gold catalyst. The former reactions probably proceed via activation of the electrophile, whilst the latter reactions proceed via a gold(I) acetylide intermediate. Gold-catalysed halogenation was further combined with gold-catalysed hydration and subsequent annulation to provide convenient routes to iodomethyl ketones and five-membered aromatic heterocycles. Copyright
- Starkov, Pavel,Rota, Filippo,D'Oyley, Jarryl M.,Sheppard, Tom D.
-
supporting information
p. 3217 - 3224
(2013/01/15)
-
- Solid-phase organic synthesis of α-iodo ketones using recyclable resin-bound selenium bromide
-
A novel facile method for the traceless solid-phase synthesis of α-iodo ketones using a recyclable resin-bound selenium bromide reagent is reported. Various ketones and α-dicarbonyl compounds can be converted to the corresponding α-iodo-substituted compou
- Mao, Xue-Chun,Liu, Xiao-Ling,Deng, Qiang,Sheng, Shou-Ri
-
experimental part
p. 100 - 102
(2012/04/23)
-
- I2/CuO-catalyzed tandem cyclization strategy for one-pot synthesis of substituted 2-aminothiozole from easily available aromatic ketones/α,β-unsaturated ketones and thiourea
-
A concise and efficient one-pot process from easily available methyl ketones/unsaturated methyl ketones and thiourea was developed for the synthesis of 2-aminothiazoles under the media of I2/CuO. The method can highly stereoselectivity obtain the E-isomers of 4-ethenyl-2-aminothiazoles (5a-f). All these target molecules were characterized by NMR, HRMS and IR spectra. Furthermore, the target compounds 3c and 5b were further determined by X-ray crystallographic analysis.
- Zhu, Yan-Ping,Yuan, Jing-Jing,Zhao, Qin,Lian, Mi,Gao, Qing-He,Liu, Mei-Cai,Yang, Yan,Wu, An-Xin
-
supporting information; experimental part
p. 173 - 178
(2012/01/05)
-
- Logic design and synthesis of quinoxalines via the integration of iodination/oxidation/cyclization sequences from ketones and 1,2-diamines
-
A novel protocol for the synthesis of quinoxalines has been developed from simple ketones and 1,2-diamines. This process underwent a logic approach to bis-substituted quinoxalines via a consecutive iodination/Kornblum oxidation/cyclization in the presence of I2/CuO/DMSO and to mono-substituted quinoxalines via an iodination/cyclization/aromatization in the presence of I2/CuO/K3PO4·3H 2O.
- Lian, Mi,Li, Qi,Zhu, Yanping,Yin, Guodong,Wu, Anxin
-
p. 9598 - 9605
(2012/11/07)
-
- Oxidative iodination of carbonyl compounds using ammonium iodide and oxone
-
A simple, efficient, mild, and regioselective method for oxyiodination of carbonyl compounds has been reported by using NH4I as the source of iodine and Oxone as an oxidant. Various carbonyl compounds such as aralkyl ketones, aliphatic ketones (acyclic and cyclic), and β-keto esters proceeded to the respective α-monoiodinated products in moderate to excellent yields. Unsymmetrical aliphatic ketones reacted smoothly yielding a mixture of 1-iodo and 3-iodo ketones with the predominant formation of 1-iodoproduct.
- Marri, Mahender Reddy,MacHarla, Arun Kumar,Peraka, Swamy,Nama, Narender
-
supporting information; experimental part
p. 6554 - 6559
(2012/01/02)
-
- The conversion of aryl and heteroaryl methylketones to the corresponding secondary or tertiary amides
-
Secondary or tertiary amides have been prepared directly from aryl, heteroaryl methyl ketones using an iodineamine-NaOH system which afforded the expected products in good yields in an aqueous medium. The present method has the advantages of using inexpensive reagents, mild reaction condition and ease of manipulation.
- Ding, Jiaoyang,Cao, Liping,Wang, Jungang,Xue, Weijian,Zhu, Yanping,Wu, Anxin
-
experimental part
p. 298 - 301
(2011/10/02)
-
- An efficient method for synthesis of phenacyl derivatives under homogeneous phase transfer catalyst condition in aqueous media
-
In this letter, a mild and efficient procedure for synthesis of phenacyl derivatives under homogenous catalysis in the presence of tetrabutylammonium bromide in aqueous media is described. The nucleophilic substitution reactions were performed under ecofriendly conditions and gave the corresponding products in high yields and short reaction times.
- Sayyahi, Soheil,Saghanezhad, Jafar
-
experimental part
p. 300 - 302
(2012/01/14)
-
- Functionalized 3(2H)-furanones via photooxygenation of (β-keto)-2- substituted furans: Application to the biomimetic synthesis of merrekentrone C
-
Photooxygenation of (β-keto)-2-substituted furans leads, in a one pot operation, to functionalized 3(2H)-furanones with good to excellent yields. This methodology was applied as a key-step to the concise and biomimetic synthesis of the sesquiterpene merre
- Gryparis, Charis,Lykakis, Ioannis N.,Efe, Christina,Zaravinos, Ioannis-Panayotis,Vidali, Theonymphi,Kladou, Eugenia,Stratakis, Manolis
-
supporting information; experimental part
p. 5655 - 5658
(2011/09/16)
-
- Facile aerobic photo-oxidative synthesis of phenacyl iodides and bromides from styrenes using I2 or aqueous HBr
-
We report a useful method for facile synthesis of phenacyl iodides and bromides from styrene derivatives by aerobic photo-oxidation using I2 or 48% aqueous HBr in the presence of water. Georg Thieme Verlag Stuttgart - New York.
- Nobuta, Tomoya,Hirashima, Shin-Ichi,Tada, Norihiro,Miura, Tsuyoshi,Itoh, Akichika
-
experimental part
p. 2335 - 2339
(2010/11/04)
-
- Formation of unsymmetrical 1,4-enediones via A focusing domino strategy: Cross-coupling of 1,3-dicarbonyl compounds and methyl ketones or terminal aryl alkenes
-
A highly efficient synthesis of unsymmetrical 1,4-enediones from 1,3-dicarbonyl compounds and methyl ketones or terminal aryl alkenes has been developed via a focusing domino strategy. Simple and readily available starting materials, mild reaction conditions, and a very simple operation are advantages of the reaction, which allow straightforward synthesis of a variety of unsymmetrical 1,4-enediones.
- Gao, Meng,Yang, Yan,Wu, Yan-Dong,Deng, Cong,Cao, Li-Ping,Meng, Xiang-Gao,Wu, An-Xin
-
supporting information; experimental part
p. 1856 - 1859
(2010/10/03)
-
- Fluorescent analogues of the insect neuropeptide helicokinin I: Synthesis, photophysical characterization and biological activity
-
In insects numerous physiological processes are regulated by neuropeptides. Two fluorescent analogues of the amino acids tryptophan and tyrosine were synthesized and incorporated in the diuretic neuropeptide helicokinin I from the moth Heliothis zea. By fluorescence emission measurements it was shown that both fluorescent helicokinin I analogues react sensitive on the dielectricity of their microenvironment. A helicokinin I analogue containing the fluorescent tryptophan mimic β-[6'-(N,N-dimethyl)-amino-2'-naphthoyl]alanine (Ald) was shown to bind to dodecylphosphocholine (DPC) micelles by the Ald residue. A membrane binding model for helicokinin I is proposed based on data from related mammalian and insect-neuropeptides.
- Chen, Heru,Scherkenbeck, Juergen,Zdobinsky, Tino,Antonicek, Horst
-
scheme or table
p. 431 - 436
(2011/12/14)
-
- Aerobic oxidative iodination of ketones catalysed by sodium nitrite "on water" or in a micelle-based aqueous system
-
Selective and efficient aerobic oxidative iodination of ketones in aqueous media was achieved by using molecular iodine as the source of iodine atoms, air as the terminal oxidant, sodium nitrite (NaNO2) as the catalyst and H2SO4
- Stavber, Gaj,Iskra, Jernej,Zupan, Marko,Stavber, Stojan
-
supporting information; experimental part
p. 1262 - 1267
(2010/05/02)
-
- Direct conversion of aromatic ketones to arenecarboxylic esters via carbon-carbon bond-cleavage reactions
-
Aromatic methyl ketones, ss-keto esters, and trifluoromethyl-l,3- diketones can be directly converted to arene-carboxylic esters via carbon-carbon bond cleavage of pyridinium iodide intermediates in the presence of copper(II) oxide, iodine, pyridine, and potassium carbonate in alcoholic media. The advantages of the present method in terms of good yields, mild reaction conditions, and inexpensive reagents should make this protocol a valuable alternative to the existing methods.
- Yin, Guodong,Gao, Meng,Wang, Zihua,Wu, Yandong,Wu, Anxin
-
scheme or table
p. 369 - 372
(2009/04/07)
-
- N-Phenethyl and N-naphthylmethyl isatins and analogues as in vitro cytotoxic agents
-
A range of N-phenethyl, N-phenacyl, and N-(1- and 2-naphthylmethyl) derivatives of 5,7-dibromoisatin 2 were prepared by N-alkylation reactions. Their activity against human monocyte-like histiocytic lymphoma (U937), leukemia (Jurkat), and breast carcinoma
- Matesic, Lidia,Locke, Julie M.,Bremner, John B.,Pyne, Stephen G.,Skropeta, Danielle,Ranson, Marie,Vine, Kara L.
-
p. 3118 - 3124
(2008/09/20)
-
- Iodination of organic compounds with elemental iodine in the presence of hydrogen peroxide in ionic liquid media
-
Iodo-transformations using the reagent system I2/H 2O2 were studied in the water miscible ionic liquid (IL) 1-butyl-3-methyl imidazolium tetrafluoroborate (bmimBF4) and in water immiscible IL, 1-butyl-3-methyl i
- Pavlinac, Jasminka,Laali, Kenneth K.,Zupan, Marko,Stavber, Stojan
-
experimental part
p. 946 - 955
(2009/04/05)
-
- Highly efficient and clean method for direct α-iodination of aromatic ketones
-
Under neutral reaction conditions, aromatic ketones were transformed into the corresponding α-iodo ketones in high yields by the combination of copper(II) oxide and iodine. The reaction mechanism showed that copper(II) oxide played multiple roles through random self-sorting. Georg Thieme Verlag Stuttgart.
- Yin, Guodong,Gao, Meng,She, Nengfang,Hu, Shengli,Wu, Anxin,Pan, Yuanjiang
-
p. 3113 - 3116
(2008/09/16)
-
- Solvent-free iodination of organic molecules using the I 2/urea-H2O2 reagent system
-
Introduction of iodine under solvent-free conditions into several aromatic compounds activated toward electrophilic functionalisation was found to proceed efficiently using elemental iodine in the presence of a solid oxidiser, the urea-H2O2 (UHP) adduct. Two types of iodo- functionalisation through an electrophilic process were observed: iodination of an aromatic ring, and side-chain iodo-functionalisation in the case of arylalkyl ketones. Two reaction routes were established based on the required substrate: iodine: oxidiser ratio for the most efficient iodo-transformation, and the role of UHP was elucidated in each route. The first, requiring a 1: 0.5: 0.6 stoichiometric ratio of substrate to iodine to UHP, followed the atom economy concept in regard to iodine and was valid in the case of aniline (1a), 4-t-Bu-phenol (3), 1,2-dimethoxy benzene (5a), 1,3-dimethoxy benzene (5b), 1,2,3-trimethoxy benzene (7a), 1,2,4-trimethoxy benzene (7b), 1,3,5-trimethoxy benzene (7c), 1-indanone (11a) and 1-tetralone (11b). The second reaction route, where a 1: 1: 1 stoichiometric ratio of substrate: I2: UHP was needed for efficient iodination, was suitable for side-chain iodo-functionalisations of acetophenone (1c) and methoxy-substituted acetophenones. Moreover, addition of iodine to 1-octene (13a) and some phenylacetylenic derivatives (15a, 15b) was found to proceed efficiently without the presence of any oxidiser and solvent at room temperature. This journal is The Royal Society of Chemistry.
- Pavlinac, Jasminka,Zupan, Marko,Stavber, Stojan
-
p. 699 - 707
(2008/03/27)
-
- Efficient C-C double-bond formation reaction via a new synthetic strategy: A self-sorting tandem reaction
-
A novel and efficient carbon-carbon double-bond formation reaction via coupling of aryl or heteroaryl methyl ketones has been developed. A dimethyl sulfoxide-iodine-CuO system was proven to be efficient for this reaction and afforded the expected products in good yields. A new synthetic strategy, a self-sorting tandem reaction, was involved in this type of reaction and was presented for the first time.
- Yin, Guodong,Zhou, Baohan,Meng, Xianggao,Wu, Anxin,Pan, Yuanjiang
-
p. 2245 - 2248
(2007/10/03)
-
- Effect of water on the functionalization of substituted anisoles with iodine in the presence of F-TEDA-BF4 or hydrogen peroxide
-
Water was found to be a convenient reaction medium for functionalization of substituted anisoles using iodine in the presence of Selectfluor F-TEDA-BF 4 or hydrogen peroxide as mediators and oxidizers. Two types of functionalization were observ
- Pavlinac, Jasminka,Zupan, Marko,Stavber, Stojan
-
p. 1027 - 1032
(2007/10/03)
-
- Metal catalyst-free direct α-iodination of ketones with molecular iodine
-
Ketones are directly converted to the corresponding α-iodoketones in good yields with molecular iodine under metal catalyst-free conditions. A significant difference in the reactivities was observed for aliphatic and aromatic ketones; whereas aliphatic ke
- Rao, Maddali L.N.,Jadhav, Deepak N.
-
p. 6883 - 6886
(2007/10/03)
-
- Efficient microwave induced direct α-halogenation of carbonyl compounds
-
A novel and direct method for the synthesis of α-halocarbonyl compounds using sequential treatment of carbonyl compounds with [hydroxy(tosyloxy)iodo]benzene followed by magnesium halides under solvent-free microwave irradiation conditions is described.
- Lee, Jong Chan,Park, Jin Young,Yoon, So Young,Bae, Yong Hun,Lee, Seung Jun
-
p. 191 - 193
(2007/10/03)
-
- Efficient α-iodination of carbonyl compounds under solvent-free conditions using microwave irradiation
-
Direct conversion of carbonyl compounds into α-iodocarbonyl compounds has been successfully achieved under solvent-free microwave irradiation conditions using N-iodosuccinimide and p-toluenesulfonic acid.
- Lee, Jong Chan,Bae, Yong Hun
-
p. 507 - 508
(2007/10/03)
-
- Direct α-iodination of aryl alkyl ketones by elemental iodine activated by 1-chloromethyl-4-fluoro-1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate)
-
Selective introduction of an iodine atom at the α-carbonyl position in various aryl alkyl ketones was effectively achieved by reaction of target molecules with elemental iodine in the presence of N-F reagents. The best results were obtained by using 1-chl
- Jereb, Marjan,Stavber, Stojan,Zupan, Marko
-
p. 853 - 858
(2007/10/03)
-
- Selectfluor F-TEDA-BF4 mediated and solvent directed iodination of aryl alkyl ketones using elemental iodine
-
Reactions of aryl alkyl ketones with methanol solution of elemental iodine and 1-fluoro-4-chloromethyl-1,4-diazonia-bicyclo[2.2.2]octane bis(tetrafluoroborate) (Selectfluor F-TEDA-BF4) result in the formation of corresponding α-iodo ketones, wh
- Stavber, Stojan,Jereb, Marjan,Zupan, Marko
-
p. 488 - 489
(2007/10/03)
-