- An Oxidation Study of Phthalimide-Derived Hydroxylactams
-
A systematic study of the oxidation of 3-hydroxy-2-substituted isoindolin-1-ones (hy-droxylactams) and their conversion to the corresponding phthalimides was undertaken using three oxidants. Of special interest was the introduction of nickel peroxide (NiO2 ) as an oxidation system for hydroxylactams and comparison of its performance with the commonly used pyridinium chlorochromate (PCC) and iodoxybenzoic acid (IBX) reagents. Using a range of hydroxylactams, optimal conversions of these substrates to the corresponding imides was achieved with 50 equivalents of freshly prepared NiO2 in refluxing toluene over 5–32 h reaction times. By comparison, oxidations of the same substrates using PCC/silica gel (three equivalents) and IBX (three equivalents) required oxidation times of 1–3 h for full conversion but required lengthier purification. While nominal amounts (~25 mg) of substrate hydroxylactams were used to ascertain conversion, scale-up procedures using all three methods gave good to excellent isolated yields of imides.
- Adjei, Bernard L.,Luzzio, Frederick A.
-
-
- “On water” nano-Cu2O-catalyzed CO-free one-pot multicomponent cascade cyanation-annulation-aminolysis reaction toward phthalimides
-
An efficient nano-Cu2O-catalyzed cascade multicomponent reaction of 2-halobenzoic acids and trimethylsilyl cyanide with diverse amines was developed using water as a solvent, affording versatileN-substituted phthalimide derivatives in moderate to excellent yields. This novel strategy features carbon monoxide gas-free, environmentally benign, one-pot multistep transformation, commercially available reagents, a cheap catalyst without any additives, wide functional group tolerance, and operational convenience.
- Wen, Xiaowei,Liu, Xiaojuan,Yang, Zhiqi,Xie, Menglan,Liu, Yuxi,Long, Lipeng,Chen, Zhengwang
-
supporting information
p. 1738 - 1743
(2021/03/14)
-
- Visible-Light-Induced Metal-/Photocatalyst-Free C-H Bond Imidation of Arenes
-
In this study, a visible-light-induced intermolecular C-H bond imidation of arenes was achieved at ambient condition. By using simple phthalimide with (diacetoxyiodo)benzene and molecular iodine, direct metal-/photocatalyst-free C-N bond formation was achieved. The imidation protocol was designed by using time-dependent density functional theory calculations and experimentally demonstrated for 28 substrates with as high as 96% yield. Mechanistic studies indicated that radical-mediated aromatic substitution occurred via photolysis of N-iodophthalimide under visible-light irradiation.
- Kuribara, Takahito,Nakajima, Masaya,Nemoto, Tetsuhiro
-
supporting information
p. 2235 - 2239
(2020/03/13)
-
- Ru-Catalyzed Selective C-H Bond Hydroxylation of Cyclic Imides
-
We report on cyclic imides as weak directing groups for selective monohydroxylation reactions using ruthenium catalysis. Whereas acyclic amides are known to promote the hydroxylation of the C(sp2)-H bond enabling five-membered ring ruthenacycle intermediates, the cyclic imides studied herein enabled the hydroxylation of the C(sp2)-H bond via larger six-membered ruthenacycle intermediates. Furthermore, monohydroxylated products were exclusively obtained (even in the presence of overstoichiometric amounts of reagents), which was rationalized by the difficulty to accommodate coplanar intermediates once the first hydroxyl group was introduced into the substrate. The same reactivity was observed in the presence of palladium catalysts.
- Yuan, Yu-Chao,Bruneau, Christian,Dorcet, Vincent,Roisnel, Thierry,Gramage-Doria, Rafael
-
p. 1898 - 1907
(2019/02/05)
-
- Palladium Catalyzed Regioselective Synthesis of Substituted Biaryl Amides through Decarbonylative Arylation of Phthalimides
-
The Pd(OAc)2 catalyzed cross-coupling of N-substituted phthalimides with aryl halide provides a single step direct access of a wide range of synthetically appealing ortho-substituted biarylamides in high yields through unique carbonyl (CO) replacement. The reaction proceeds through a ligand-free condition and is well tolerant to the diverse functionality of both imide and halide units. The reaction negates any requirement of organometallic reagent and needs a shorter reaction time and comparatively lower temperature as required for previously reported decarbonylative processes.
- Samanta, Partha Kumar,Biswas, Papu
-
p. 3968 - 3976
(2019/03/26)
-
- Br?nsted acid mediated intramolecular cyclopropane ring expansion/[4 + 2]-cycloaddition
-
A cascade reaction of 3-hydroxy-2-phenylisoindolin-1-one and cyclopropyl ketone has been developed via a Br?nsted acid-promoted ring-opening/intramolecular cross-cycloaddition/[4 + 2]-cycloaddition process. The developed methodology provides straightforward access to pentacyclic isoindolin-1-one derivatives under simple reaction conditions.
- Li, Jian,Zhu, Shangrong,Xu, Qiuneng,Liu, Li,Yan, Shenghu
-
p. 10004 - 10008
(2019/12/23)
-
- Novel method for constructing N-(4-bromophenyl)phthalimide for one step from imine as initial raw material
-
The invention discloses a method for constructing N-(4-bromophenyl)phthalimide for one step from imine as an initial raw material. The method uses (E)-N-(4-bromophenyl)-1-phenyl methylenimine as a reaction raw material for constructing the N-(4-bromopheny
- -
-
Paragraph 0018; 0022-0048
(2019/01/14)
-
- Carbonylation Access to Phthalimides Using Self-Sufficient Directing Group and Nucleophile
-
Herein we report a novel palladium-catalyzed oxidative carbonylation reaction for the synthesis of phthalimides with high atom- and step-economy. In our strategy, the imine and H2O, which are generated in situ from the condensation of aldehyde and amine, serve as self-sufficient directing group and nucleophile, respectively. This method provides rapid access to phthalimides starting from readily available materials in a one-pot manner. Various phthalimide derivatives are constructed efficiently, including medicinally and biologically active phthalimide-containing compounds.
- Ji, Fanghua,Li, Jianxiao,Li, Xianwei,Guo, Wei,Wu, Wanqing,Jiang, Huanfeng
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p. 104 - 112
(2018/02/19)
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- NITROGEN-CONTAINING BIOPOLYMER-BASED CATALYSTS, THEIR PREPARATION AND USES IN HYDROGENATION PROCESSES, REDUCTIVE DEHALOGENATION AND OXIDATION
-
The present invention relates to a process for the preparation of a nitrogen containing biopolymer-based catalyst by pyrolysis of a metal complex with a nitrogen-containing biopolymer and to the nitrogen containing biopolymer-based catalysts obtainable by this process. In particular, the invention relates to a nitrogen containing biopolymer-based catalyst comprising metal particles and at least one nitrogen containing carbon layer. The invention also relates to the use of a nitrogen containing biopolymer-based catalyst in a hydrogenation process, preferably in a process for hydrogenation of nitroarenes, nitriles or imines; in a reductive dehalogenation process of C-X bonds, wherein X is CI, Br or I, preferably in a process for dehalogenation of organohalides or in a process for deuterium labelling of arenes via dehalogenation of organohalides; or in an oxidation process. Further, the invention relates to a metal complex with the nitrogen containing biopolymer, wherein the metal is a transition metal selected from the group consisting of manganese, ruthenium, cobalt, rhodium, nickel, palladium and platinum, preferably cobalt or nickel, and wherein the nitrogen containing biopolymer is selected from chitosan, chitin and a polyamino acid, preferably chitosan or chitin.
- -
-
Page/Page column 20-21
(2018/07/29)
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- Unmasking Amides: Ruthenium-Catalyzed Protodecarbonylation of N-Substituted Phthalimide Derivatives
-
The unprecedented transformation of a wide range of synthetically appealing phthalimides into amides in a single-step operation has been achieved in high yields and short reaction times using a ruthenium catalyst. Mechanistic studies revealed a unique, homogeneous pathway involving five-membered ring opening and CO2 release with water being the source of protons.
- Yuan, Yu-Chao,Kamaraj, Raghu,Bruneau, Christian,Labasque, Thierry,Roisnel, Thierry,Gramage-Doria, Rafael
-
supporting information
p. 6404 - 6407
(2017/12/08)
-
- Organic electroluminescence material and organic photoelectric device
-
The invention provides a compound with a structure as shown in formula I. The invention also provides an application of the compound in an organic photoelectric device and the organic photoelectric device. The compound provided by the invention has a thermal activation delayed fluorescence (TADF) material luminous mechanism, can be used as a novel TADF material applied to the field of the organic photoelectric device and can increase the illuminating efficiency. No expensive metal complex is used by the compound provided by the invention; the manufacturing cost is low; the application prospect is wider.
- -
-
Paragraph 0095; 0096; 0097
(2017/07/21)
-
- PdII/AgI-Catalyzed Room-Temperature Reaction of γ-Hydroxy Lactams: Mechanism, Scope, and Antistaphylococcal Activity
-
The present work reports a PdII/AgI-promoted amidoalkylation reaction involving various γ-hydroxy lactams and C/O/S nucleophiles at room temperature. The dual mode of activation of both the electrophile and nucleophile by in situ generated catalytically active cationic PdII species facilitates the reaction at room temperature. Among the synthesized isoindoline derivatives, three compounds are found to be active against vancomycin and methicillin-resistant S. aureus strain with appreciable MIC values.
- Dutta, Manali,Mandal, Santi M.,Pegu, Rupa,Pratihar, Sanjay
-
p. 2193 - 2198
(2017/03/01)
-
- Palladium-Catalyzed Synthesis of 1H-Indenes and Phthalimides via Isocyanide Insertion
-
A new and versatile multicomponent domino strategy has been developed for the synthesis of a series of 1H-indene and phthalimide derivatives from simple and readily available starting materials. This process operating under mild conditions shows a broad substrate scope with moderate to excellent yields.
- Wang, Xu,Xiong, Wenfang,Huang, Yubing,Zhu, Jiayi,Hu, Qiong,Wu, Wanqing,Jiang, Huanfeng
-
p. 5818 - 5821
(2017/11/10)
-
- A Biomass-Derived Non-Noble Cobalt Catalyst for Selective Hydrodehalogenation of Alkyl and (Hetero)Aryl Halides
-
Hydrodehalogenation is a straightforward approach for detoxifications of harmful anthropogenic organohalide-based pollutants, as well as removal of halide protecting groups used in multistep syntheses. A novel sustainable catalytic material was prepared from biowaste (chitosan) in combination with an earth-abundant cobalt salt. The heterogeneous catalyst was fully characterized by transmission electron microscope, X-ray diffraction, and X-ray photoelectron spectroscopy measurements, and successfully applied to hydrodehalogenation of alkyl and (hetero)aryl halides with broad scope (>40 examples) and excellent chemoselectivity using molecular hydrogen as a reductant. The general usefulness of this method is demonstrated by successful detoxification of non-degradable pesticides and fire retardants. Moreover, the potential of the catalyst as a deprotection tool is demonstrated in a multistep synthesis of (±)-peronatin B (alkaloid).
- Sahoo, Basudev,Surkus, Annette-Enrica,Pohl, Marga-Martina,Radnik, J?rg,Schneider, Matthias,Bachmann, Stephan,Scalone, Michelangelo,Junge, Kathrin,Beller, Matthias
-
supporting information
p. 11242 - 11247
(2017/09/02)
-
- Thermolysis and radiofluorination of diaryliodonium salts derived from anilines
-
Aniline-derived diaryliodonium salts were synthesized and functionalized in good to excellent yields by judicious utilization of electron-withdrawing protecting groups. This simple approach opens another route to radiolabeling amino arenes in relatively complex molecules, such as flutemetamol.
- Linstad, Ethan J.,Vāvere, Amy L.,Hu, Bao,Kempinger, Jayson J.,Snyder, Scott E.,DiMagno, Stephen G.
-
supporting information
p. 2246 - 2252
(2017/03/17)
-
- Synthetic method for N-substituted imide
-
The invention provides a synthetic method for N-substituted imide. According to the method, aromatic ketone and amine are used as substrates, air or oxygen is used as an oxygen source, and cyclic imide is produced under liquid phase conditions under the action of a catalyst. The method is mild in conditions, high in oxidation efficiency and high in product yield; and since the method uses air or oxygen as the oxygen source, the method is economic and environment-friendly and has good application prospect.
- -
-
Paragraph 0016; 0028; 0029; 0030; 0031
(2017/04/20)
-
- A facile and practical copper diacetate mediated, ligand free C-N cross coupling of trivalent organobismuth compounds with amines and N-heteroarenes
-
In present work, an efficient Cu(OAc)2·H2O catalyzed protocol in the absence of any additional ligand has been developed for the N-arylation of amines and nitrogen containing heterocycles using trivalent organobismuth reagents under mild conditions. This protocol tolerates a variety of functional groups on amines and the organobismuth reagent with a high degree of chemoselectivity.
- Jadhav,Pardeshi
-
p. 14531 - 14537
(2016/02/19)
-
- Stable and Reusable Binaphthyl-Supported Palladium Catalyst for Aminocarbonylation of Aryl Iodides
-
A binaphthyl-supported Pd nanoparticles (Pd-BNP)-catalyzed aminocarbonylation of aryl iodides in the presence of carbon monoxide and amines for the synthesis of amides has been developed. This methodology provides an efficient route for the synthesis of a COX-2 enzyme inhibitor having anti-inflammatory activity.
- Sharma, Nidhi,Sekar, Govindasamy
-
p. 314 - 320
(2016/02/14)
-
- Cuprous Oxide Catalyzed Oxidative C-C Bond Cleavage for C-N Bond Formation: Synthesis of Cyclic Imides from Ketones and Amines
-
Selective oxidative cleavage of a C-C bond offers a straightforward method to functionalize organic skeletons. Reported herein is the oxidative C-C bond cleavage of ketone for C-N bond formation over a cuprous oxide catalyst with molecular oxygen as the oxidant. A wide range of ketones and amines are converted into cyclic imides with moderate to excellent yields. In-depth studies show that both α-C-H and β-C-H bonds adjacent to the carbonyl groups are indispensable for the C-C bond cleavage. DFT calculations indicate the reaction is initiated with the oxidation of the α-C-H bond. Amines lower the activation energy of the C-C bond cleavage, and thus promote the reaction. New insight into the C-C bond cleavage mechanism is presented.
- Wang, Min,Lu, Jianmin,Ma, Jiping,Zhang, Zhe,Wang, Feng
-
supporting information
p. 14061 - 14065
(2016/01/25)
-
- Regioselective gold-catalyzed oxidative C-N bond formation
-
A novel protocol for the regioselective intermolecular amination of various arenes has been developed. By using an I(III) oxidant in the presence of a Au(I) catalyst, a direct and novel route for regioselectively accessing a variety of substituted aniline moieties has been achieved with yields as high as 90%. Mechanistic insight suggests that regioselectivity can be predicted based on electrophilic aromatic metalation patterns.
- Marchetti, Louis,Kantak, Abhishek,Davis, Riley,Deboef, Brenton
-
supporting information
p. 358 - 361
(2015/01/30)
-
- A phthalimidation protocol that follows protein defined parameters
-
This work outlines the first phthalimidation protocol suitable for protein labeling and performed in aqueous media at room temperature and neutral pH with no catalyst or co-reagent required. The methodology is suitable for a range of amines and its efficiency was determined with chemoselective and site-selective protein labeling. This journal is
- Singudas, Rohith,Adusumalli, Srinivasa Rao,Joshi, Pralhad Namdev,Rai, Vishal
-
supporting information
p. 473 - 476
(2015/01/09)
-
- An expeditious synthesis of imides from phthalic, maleic and succinic anhydrides and chemoselective C=C reduction of maleic amide esters
-
Phthalic, maleic and succinic anhydrides have been reacted with aromatic amines to obtain the corresponding monoacid monoamides. The latter have been each transformed into the corresponding cyclic imide derivatives by treating with SOCl2. Alternatively, anhydrides have been reacted with methanolic KOH to obtain monomethyl ester derivatives which on reaction with aromatic amines in the presence of EDC. HCl and HOBt give cyclic imide derivatives. Reaction of monoacid monoamides independently, with SOCl 2 at 0-5°C give the monoamide monoester derivatives. Treatment of monoamide monoester of malic anhydride with NaBH4 leads to the unusual reduction of C=C grouping as well as the carbonyl group of the ester group to from monoamide monoalcohol of succinic anhydride. Preparation of monoamide monoalcohol of succinic anhydride can also be achieved by chemoselective reduction of monoamide monoester of malic anhydride with Mg turnings yielding monoamide monoester of succinic anhydride followed by reduction of the latter with NaBH4.
- Kumar, Padam Praveen,Reddy, Y. Dathu,Kumari, Y. Bharathi,Devi, B. Rama,Dubey
-
p. 392 - 398
(2014/05/06)
-
- Nitrogen-centered radical-mediated C-H imidation of arenes and heteroarenes via visible light induced photocatalysis
-
The C-H imidation of arenes and heteroarenes has been achieved via visible light induced photocatalysis. In the presence of an iridium(iii) photoredox catalyst, the reaction of aromatic substrates with N-chlorophthalimide furnishes the N-aryl products at room temperature through a nitrogen-centered radical mediated aromatic substitution.
- Kim, Hyejin,Kim, Taehoon,Lee, Dong Gil,Roh, Sang Weon,Lee, Chulbom
-
supporting information
p. 9273 - 9276
(2014/08/05)
-
- Catalyst-free, eco-friendly, one-pot syntheses of 2-(3H-imidazo [4,5-b] pyridine-2-yl)-N-arylbenzamides in water
-
Eco-friendly, one-pot three-component syntheses of 2-(3H-imidazo [4,5-b]pyridine-2-yl)-N-arylbenzamides have been developed by combining phthalic anhydride with anilines and pyridine-2,3-diamine in water without any catalyst. These reactions involves easy workup, provide good yields and use of water as solvent which were the merits of this preparation.
- Reddy, Y. Dathu,Kumar, P. Praveen,Devi, B. Rama,Reddy, Ch. Venkata Ramana,Dubey
-
p. 768 - 773
(2015/04/14)
-
- A facile and green synthesis of N-substituted imides
-
Anhydrides 1, 6 and 10 have been reacted, independently, with aromatic primary amines 2 in solid phase by simple physical grinding of reactants with p-toluenesulphonicacid as a catalyst to yield corresponding open chain derivatives, monoacid monoamides3,7 and 11 respectively. The latter have each been transformed into the corresponding cyclic derivatives, i.e. imides 5, 9 and 13 respectively in solid phase by simple physical grinding of each with K 2CO3, alkylating agent and tetrabutylammoniumbromide as a catalyst with short reaction times. These cyclic imides can also be obtained by physical grinding of each of 3, 7 and 11 with dicyclohexylcarbodimide as a dehydrating agent in solid phase.
- Kumar, Padam Praveen,Rama Devi,Dubey
-
p. 1166 - 1171
(2013/09/24)
-
- Sterically controlled, palladium-catalyzed intermolecular amination of arenes
-
We report the Pd-catalyzed amination of arenes to form N-aryl phthalimides with regioselectivity controlled predominantly by steric effects. Mono-, di-, and trisubstituted arenes lacking a directing group undergo amination reactions with moderate to high yields and high regioselectivities from sequential addition of PhI(OAc)2 as an oxidant in the presence of Pd(OAc) 2 as catalyst. This sterically derived selectivity contrasts that for analogous arene acetoxylation.
- Shrestha, Ruja,Mukherjee, Paramita,Tan, Yichen,Litman, Zachary C.,Hartwig, John F.
-
supporting information
p. 8480 - 8483
(2013/07/19)
-
- Imidazole-promoted synthesis of n-substituted phthalimide from N,N'-disubstituted ureas in solventless conditions
-
A series of N-substituted phthalimides was synthesized by a thermal reaction between N,N0-disubstituted ureas and phthalic acid catalyzed by imidazole in solventless conditions. The products have been obtained in moderate to good yields (53-92%). Supplemental materials are available for this article. Go to the publisher's online edition of Synthetic Communications1 to view the free supplemental file. Copyright Taylor & Francis Group, LLC.
- Neves Filho, Ricardo A. W.,Palm-Forster, Mieder A. T.,De Oliveira, Ronaldo N.
-
supporting information
p. 1571 - 1576
(2013/05/22)
-
- An environmentally benign solvent/catalyst-free one-pot synthesis of N-substituted phthalimides via Aza-wittig reaction
-
For the first time an environmentally benign solvent/catalyst-free protocol for the synthesis of a variety of N-substituted phthalimides is submitted. It involves a one-pot coupling of nascent phosphazene generated in situ with phthalic anhydride. The protocol is novel in (1) avoiding toxic solvents, (2) no catalyst is employed and (3) no isophthalimide is formed as noted in the prevailing solution phase/catalysed methodology. Iranian Chemical Society 2012.
- Sathishkumar, Murugan,Palanikumar, Kulandaivel,Mariappan, Arumugam,Archana, Sivasubramaniyan,Ponnuswamy, Alagusundaram
-
p. 681 - 685
(2013/02/22)
-
- An efficient protocol for the synthesis of N-Alkyl- and N-Arylimides using the lewis acidic ionic liquid choline chloride-2ZnCl2
-
Lewis acidic ionic liquid choline chloride-2ZnCl2 is shown to be for the first time an excellentmedium and efficient catalyst for the synthesis of N-alkyl- and N-arylimides in good yields under mild conditions.
- Xiea, You-Teng,Houb, Rei-Sheu,Wangb, Huey-Min,Kangc, Iou-Jiun,Chena, Ling-Ching
-
experimental part
p. 839 - 842
(2010/08/13)
-
- Palladium-catalyzed one-step synthesis of isoindole-1,3-diones by carbonylative cyclization of o-halobenzoates and primary amines
-
(Chemical Equation Presented) The palladium-catalyzed aminocarbonylation of o-halobenzoates produces 2-substituted isoindole-1,3-diones in good yields. This methodology provides a good one-step approach to this important class of heterocycles and tolerates a variety of functional groups, including methoxy, alcohol, ketone, and nitro groups.
- Worlikar, Shilpa A.,Larock, Richard C.
-
supporting information; experimental part
p. 7175 - 7180
(2009/05/09)
-
- Synthesis and screening of anilides having olefinic and alkyl moiety in the side chain as chemical hybridizing agents for wheat (Triticum aestivum L.)
-
Induction of male sterility by deployment of chemical hybridizing agents (CHAs) holds immense potential in heterosis breeding of wheat. A total of 21 anilides having different aromatic substitutions and side-chain variation were synthesized and screened as CHAs on three genotypes of wheat viz., PBW 343, HW 2046, and HD 2733, at winter season. Various anilides having vinyl moiety in the acyl side chain were synthesized by condensation between substituted anilines with different esters or acid chlorides. Another lead in the form of N-alkyl anilines also became evident. The percent male sterility data caused by CHAs revealed the significant contribution of anilides containing vinyl double bond incorporated in the form of closed ring structure viz., furyl moiety as the side chain. 4′-Fluoro-furyl anilide (1) and 4′-bromo-furyl anilide (2) are found to be promising lead CHAs for the design of highly active molecules. QSAR analysis revealed a direct relationship of field effect exemplified by the Swain-Lupton constant Fp for the aromatic substitution but an inverse relationship of molar refractivity MR for the side chain. The negative influences of parachor for the acyl domain have been underlined. The real guiding principle for selectivity of CHA action was found to be the π value. The CHAs act by mimicking UDP-glucose, the key substrate in the synthesis of callose, or lead to an imbalance in acid-base equilibrium in pollen mother cells resulting in dissolution of callose wall by premature callase secretion.
- Chakraborty, Kajal,Devakumar
-
p. 5959 - 5968
(2007/10/03)
-
- A convenient procedure for the synthesis of phthalimides under microwave irradiation
-
An efficient, extremely fast and clean procedure for the synthesis of phthalimides 2 and 3 by the reaction of phthalic anhydrides 1 with urea and aromatic amines in the presence of catalytic amount of DMF under microwave irradiation is described. The products are obtained in quantitative yields and excellent purities.
- Mogilaiah,Reddy, G. Randheer
-
p. 882 - 884
(2007/10/03)
-
- A New Simple and Efficient Synthesis of N-Aryl Phthalimides in Ionic Liquid [bmim][PF6]
-
The room temperature ionic liquid [bmim][PF6], namely 1-butyl-3-methyl-imidazolium hexafluorophosphate, is used as an alternative solvent to classic solvents for the synthesis of a series of N-aryl phthalimides in good to excellent yields.
- Zhou, Mei-Yun,Li, Yi-Qun,Xu, Xin-Ming
-
p. 3777 - 3780
(2007/10/03)
-
- A rapid synthesis of N-aryl phthalimides under microwave irradiation in the absence of solvent
-
A mixture of phthalic anhydride (1) and aromatic amines (2a-h) were irradiated in a microwave oven for 2-10 min to provide N-aryl phthalimides (3a-h) in 91-95% yields.
- Li, Hui-Zhang,Zhang, Jin-Song,Zhou, Ya-Ming,Li, Tong-Shuang
-
p. 927 - 930
(2007/10/03)
-
- Indoloquinones, Part 6.13 First palladium-mediated oxidative cyclization of arylamino-1,2-benzoquinones to carbazole-3,4-quinones - Application to the total synthesis of carbazoquinocin C and (±)- carquinostatin A
-
A highly convergent synthesis of the carbazole-3,4-quinone alkaloids carbazoquinocin C and (±)-carquinostatin A is reported using a palladium- mediated oxidative coupling of arylamines and substituted 1,2-benzoquinones.
- Kn?lker, Hans-Joachim,Reddy, Kethiri R.
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p. 596 - 598
(2007/10/03)
-
- Multivariate regression with substituent shift increments. IV. 2-(4-X-phenyl)-1,3-dihydro-2H-isoindole-1,3-diones and 3-(4-X-phenyl)-3,4-dihydro-2H-1,3-benzoxazine-2,4-diones
-
Two series of para disubstituted benzenes were studied: 2-(4-X-phenyl)-1,3-dihydro-2H-isoindole-1,3-diones (1) and 3-(4-X-phenyl)-3,4-dihydro-2H-1,3-benzoxazine-2,4-diones (2). Their 1H and 13C chemical shifts were correlated with substituent shift increments (SSI) aj and zj, respectively. For 13C chemical shifts, all four zj values, zj, zo, zm, and zp, were used to check the assignment and to find out possible variables for improvement of regression equations. Significant deviations from plain additivity were observed in the case of δH3 and δC3 chemical shifts. This can be explained by changes in diamagnetic anisotropy contribution induced by different twist of 4-substituent from the benzene plane caused by variable substituent in position 1.
- Holik, Miroslav,Friedl, Zdenek,Waisser, Karel,Gregor, Jiri
-
p. 1709 - 1726
(2007/10/03)
-
- Microwave Irradiation Promoted Reactions of Anhydrides with Isocyanates. Preparation of N-Substituted Phthalimides
-
The synthesis of N-substituted phthalimides by the condensation of anhydrides and isocyanates was conducted efficiently in a few minutes in unmodified commercial microwave ovens using unsealed vessels.
- Khajavi, Mohammad S.,Nikpour, Farzad,Hajihadi, Mostafa
-
-
- HYDROLYSIS OF 1-OXO-3-ETHYL-4-ARYL-2,3-BEZOXAZINIUM SALTS
-
Irrespective of the character of the substituent at position 4, the action of triethyloxonium fluoroborate on 1-oxo-4-aryl(methyl)-2,3-benzoxazines leads to the formation of 1-oxo-3-ethyl-4-aryl(methyl)-2,3-benzoxazinium tetrafluoroborates, which readily exchange the anion, being converted into the corresponding perchlorates and tetrachloroferrates.Hydrolysis of the oxobenzoxazinium perchlorates leads to 4-hydroxy-3-ethyl-4-aryl(methyl)-2,3-benzoxazin-1-ones, which exhibit the characteristics of carbinol bases.The formation of N-arylphthalimides is also observed in the case of the oxobenzoxazinium salts containing accepting or weakly don ating substituents.
- Volynets, N. F.,Samartseva, I. V.,Pavlova, L. A.
-
p. 574 - 577
(2007/10/02)
-