cas 941-69-5, N-Phenylmaleimide | Articles data

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Richards et al.
p. 485,486
(1966)
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Dual organic dyes as a pseudo-redox mediation system to promotion of tandem oxidation /[3+2] cycloaddition reactions under visible light
An atom- and step-economy protocol has been developed to synthesize some new biologically active pyrrolo[2,1-a]isoquinoline alkaloids via redox mediation system under visible light irradiation. A vast variety of double and triple bonds, as dipolarophiles, treated with in situ generated azomethine ylides to prepare corresponding products in good to excellent yields. This metal-free method effectively promoted oxidation/[3 + 2] cycloaddition/oxidative/aromatization domino reaction without further oxidant using dual organic dyes as pseudo-redox mediation system. Besides, for most of the products, product precipitate was readily separated from reaction media. To the best of our knowledge, this is the first report of dual dyes as a pseudo-redox mediation system.
Koohgard, Mehdi,Hosseinpour, Zeinab,Hosseini-Sarvari, Mona
(2021/05/10)

Visible-Light-Mediated Dearomatisation of Indoles and Pyrroles to Pharmaceuticals and Pesticides
Dearomatisation of indole derivatives to the corresponding isatin derivatives has been achieved with the aid of visible light and oxygen. It should be noted that isatin derivatives are highly important for the synthesis of pharmaceuticals and bioactive compounds. Notably, this chemistry works excellently with N-protected and protection-free indoles. Additionally, this methodology can also be applied to dearomatise pyrrole derivatives to generate cyclic imides in a single step. Later this methodology was applied for the synthesis of four pharmaceuticals and a pesticide called dianthalexin B. Detailed mechanistic studies revealed the actual role of oxygen and photocatalyst.
Schilling, Waldemar,Zhang, Yu,Riemer, Daniel,Das, Shoubhik
supporting information
p. 390 - 395
(2019/12/15)

Room-Temperature Synthesis of Isoindolone Spirosuccinimides: Merger of Visible-Light Photocatalysis and Cobalt-Catalyzed C-H Activation
A room-temperature C-H bond functionalization of benzamides has been developed by merging a photocatalyst with a cobalt catalyst for the synthesis of isoindolone spirosuccinimides. The reaction proceeds in aerobic conditions and does not require any sacrificial external oxidants such as Ag(I) or Mn(III) salts. Visible light activates the photocatalyst, and it acts as an electron-transfer reagent and helps in the fundamental organometallic steps by modulating the oxidation state of the cobalt complex. This C-H bond functionalization and spirocyclization showed wide substrate scope and good functional group tolerance. A possible reaction mechanism was proposed from the experimental outcome, showing that C-H bond activation is irreversible and not the rate-determining step.
Sen, Chiranjit,Sarvaiya, Bhavesh,Sarkar, Souvik,Ghosh, Subhash Chandra
p. 15287 - 15304
(2020/12/02)

Application of maleimide compound as chitin synthase inhibitor
The invention discloses an application of a maleimide compound as shown in a formula I. In the formula I, R0 is phenyl, benzyl, phenethyl, phenylpropyl, p-fluorophenyl, p-chlorophenyl, p-bromophenyl,p-methoxyphenyl, p-methylphenyl or p-hydroxyphenyl, R1 is hydrogen, methyl, phenyl or chlorine; and R2 is hydrogen, methyl, phenyl or chlorine. The provided maleimide compound has a good inhibition effect on chitin synthase.
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Paragraph 0024-0027

(2020/07/12)

Regioselective hydroarylation and arylation of maleimides with indazoles: Via a Rh(iii)-catalyzed C-H activation
Switchable Rh(iii)-catalyzed highly regioselective hydroarylation and oxidative arylation of maleimides with 2-arylindazoles via C-H activation have been demonstrated. The reaction affords 3-(2-(2H-indazol-2-yl)phenyl)succinimide and 3-(2-(2H-indazol-2-yl)phenyl)maleimide derivatives in high yields with wide functional group tolerance. A mechanistic study was performed to depict C-H bond cleavage that might be involved in the turnover limiting step.
Ghosh, Asim Kumar,Samanta, Sadhanendu,Ghosh, Payel,Neogi, Sukanya,Hajra, Alakananda
supporting information
p. 3093 - 3097
(2020/05/08)

Synthesis of Tetrahydroisoindolinones via a Metal-Free Dehydrogenative Diels-Alder Reaction
A metal-free dehydrogenative Diels-Alder reaction of substituted alkenes for the synthesis of tetrahydroisoindolinones has been exploited for the first time. This new method features functional group tolerance and broad substrate scope, providing an efficient access to biologically active tetrahydroisoindolinone skeletons with endo steroselectivity in good to excellent yields. (Figure presented.).
Xu, Wen-Lei,Tang, Lei,Ge, Chen-Yu,Chen, Jie,Zhou, Ling
supporting information
p. 2268 - 2273
(2019/04/10)

Synthesis and biological evaluation of novel benzylidene-succinimide derivatives as noncytotoxic antiangiogenic inhibitors with anticolorectal cancer activity in vivo
A novel series of benzylidene-succinimide derivatives were synthesized, characterized and evaluated for their cytotoxicities against HCT116, and SW480 cancer cells and NCM460 normal human cells. Their antiangiogenic capabilities were evaluated using a chick chorioallantoic membrane (CAM) assay. The compound, XCF-37b, was selected as the most potent antiangiogenic inhibitor with noncytotoxicity to evaluate the pharmacological effects on human umbilical vein endothelial cells (HUVECs) and cancer cells in vivo and in vitro. The results showed that XCF-37b inhibited HT29-cell colon tumor growth in vivo, without showing cytotoxicity against the five other cancer cell lines in vitro. Experiments confirmed that XCF-37b had obvious antiangiogenic activity by HUVEC migration and invasion and rat aortic ring angiogenesis ex vivo. Mechanism studies showed that XCF-37b inhibited the AKT/mTOR and VEGFR2 signaling pathways, as evidenced by decreased expressions of phosphor-AKT (p-AKT), p-mTOR, p-VEGFR2 (Tyr175), p-Src (Tyr416), p-FAK (Tyr925), and p-Erk1/2 (Thr202/Tyr204). Moreover, XCF-37b significantly decreased the protein expressions of matrix metalloproteinase-2 (MMP-2), MMP-9 and hypoxia-inducible factor-1α (HIF-1α). XCF-37b generally regulated angiogenic inhibition through several regulatory pathways, without significantly interfering with colorectal cancer cell growth.
Luo, Kaixiu,Bao, Yafeng,Liu, Feifei,Xiao, Chuanfan,Li, Ke,Zhang, Conghai,Huang, Rong,Lin, Jun,Zhang, Jihong,Jin, Yi
p. 805 - 827
(2019/07/10)

The base-catalysed Tamura cycloaddition reaction: Calculation, mechanism, isolation of intermediates and asymmetric catalysis
A combined experimental and computational investigation has revealed that the base-catalysed Tamura cycloaddition between homophthalic anhydride and activated alkenes/alkynes-a reaction previously thought of as a Diels-Alder type process-proceeds via a stepwise mechanism involving conjugate addition and ring closure; which allowed the first catalytic asymmetric α-substitution reactions to be demonstrated with up to >99% ee.
Lockett-Walters, Bruce,Trujillo, Cristina,Twamley, Brendan,Connon, Stephen
supporting information
p. 11283 - 11286
(2019/09/30)

Method for synthesizing N-phenylmaleimide through one-step method
The invention provided a method for synthesizing N-phenylmaleimide through a one-step method. Under the situation of not adding a polymerization inhibitor, the N-phenylmaleimide is directly synthesized by aniline and maleic anhydride through the one-step method. The method comprises the steps that a benzene solvent and a catalyst are added into a rector, maleic anhydride and a cosolvent are addedat the temperature of 50-100 DEG C, temperature increasing and reflux are conducted, then the aniline is added dropwise until the aniline is completed dropped, the time is maintained for 25-100 min, N-phenylmaleimide reaction liquid is obtained, and the yield of the reaction liquid is 98.5% or above; and the reaction liquid is washed, neutralized and distilled, and thus a product is obtained. According to the method, the time is saved, energy consumption is low, the cost is low, the working procedures are less, the content is high (can reach 99.2% or above), operation is easy, the environment-friendly effect is achieved, and the method is an improved version of a process for synthesizing N-phenylmaleimide through the one-step method.
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Paragraph 0031-0036

(2019/05/08)

SYNTHESIS METHOD OF N-SUBSTITUTED MALEIMIDE USING SOLID ACID CATALYSTS
The present invention relates to a synthesis method of N-substituted maleimides using a non-homogeneous solid acid catalyst, and particularly, a synthesis method of N-substituted maleimides with high synthesis yield by using a zirconium(IV) hydrogen phosphate as a catalyst, by which, the loss of the catalyst is minimized, the separation and recovering processes of the catalyst are simplified, in case when the activity of the separated and recovered catalyst is decreased, the complete regeneration of the catalyst is possible via washing or firing, and solvents that could be used during a washing process of the catalyst are not limited.
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Paragraph 0070-0074

(2019/06/07)

METHOD FOR PURIFYING N-SUBSTITUTED MALEIMIDE
The present invention relates to a method for purifying N-substituted maleimide comprising steps of: 1) preparing an N-substituted maleimide solution produced by conducting a reaction of maleic anhydride and primary amine in the presence of an organic solvent and a catalyst; and 2) cooling the N-substituted maleimide solution to 50 to 70anddeg;C to separate crystallized N-substituted maleimide, wherein the organic solvent is an alkane-based solvent having 9 or more carbon atoms. The method for purifying N-substituted maleimide of the present invention has an effect of being purified with high-purity N-substituted maleimide without performing a distillation process.(AA) Squalane(PMI solubility Wt.%)(BB) Temperature ( anddeg;C )COPYRIGHT KIPO 2019
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Paragraph 0113-0138

(2019/10/11)

METHOD FOR PREPARING IMIDE COMPOUNDS
The present invention relates to a method for recycling a catalyst cleaning solvent for manufacturing N-substituted maleimide and a method for manufacturing N-substituted maleimide using the same. Specifically, by a step of washing a catalyst recovered by a catalyst recovery process for manufacturing N-substituted maleimide through a washing solvent; and a step of regeneration which is adding a maleic acid isomerization catalyst to the washing solvent after washing to isomerize maleic anhydride or maleic acid included in the washing solvent into fumaric acid, and then removing and distilling the same, it is possible to regenerate and recycle the catalyst cleaning solvent for manufacturing N-substituted maleimide, thereby being able to increase economic efficiency and productivity.COPYRIGHT KIPO 2019
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Paragraph 0149-0156

(2019/10/19)

METHOD FOR PREPARING IMIDE COMPOUNDS
The present invention relates to a method for recycling N-substituted maleimide washing water and a method for manufacturing N-substituted maleimide using the same. Specifically, by adding and isomerizing a catalyst capable of isomerizing maleic anhydride or maleic acid present in the N-substituted maleimide washing waste water with fumaric acid, the washing waste water is regenerated and recycled, thereby being able to reduce additional wastewater treatment facilities and costs for maintaining the same unlike in the prior art.COPYRIGHT KIPO 2019
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Paragraph 0118-0121

(2019/10/29)

METHOD FOR RECYCLING CATALYSTS FOR PREPARING N-SUBSTITUTED MALEIMIDE
The present invention relates to a method for recycling a catalyst for manufacturing N-substituted maleimide. Specifically, by recycling a zirconium hydrogen phosphate solid acid catalyst through washing or calcining, the recycled catalyst can be reused for N-substituted maleimide synthesis.COPYRIGHT KIPO 2019
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Paragraph 0125-0140; 0149; 0152-0160

(2019/10/29)

Iron(III) Chloride/Phenylsilane-Mediated Cascade Reaction of Allyl Alcohols with Maleimides: Synthesis of Poly-Substituted γ-Butyrolactones
A iron-catalyzed free radical cascade reaction of allyl alcohols with N-substituted maleimides for accessing poly-substituted γ-butyrolactones has been developed. In this protocol, various allyl alcohols can open N-substituted maleimide rings to form allyl ester intermediates, and the allyl ester intermediates can be converted into an allyl ester alkyl radicals and undergo intramolecular free radical addition cyclization to form a polysubstituted γ-butyrolactones. In this protocol, spiro γ-butyrolactone compounds can be also synthesized. Meanwhile, the strategy could be applied to further construct a fully substituted tetrahydrofuran. The reaction is not sensitive to oxygen or moisture and has been performed on gram-scale. (Figure presented.).
Zhang, Hua,Zhan, Xiao-Yu,Chen, Xu-Ling,Tang, Lei,He, Shuai,Shi, Zhi-Chuan,Wang, Yu,Wang, Ji-Yu
supporting information
p. 4919 - 4925
(2019/11/03)

Acetylcholinesterase inhibition by products generated in situ from the transformation of N-arylisomaleimides
When N-arylisomaleimides were transformed under enzymatic reaction conditions, the transformation reaction proved to be influenced by electronic effects. This was demonstrated qualitatively by 1H NMR spectroscopy and quantitatively by monitoring the kinetic of isomerization of N-phenylisomaleimide to N-phenylmaleimide. Subsequently, the first pseudo-order and activation energy (Ea) of the process were determined. The compounds showed in situ influence on AChE inhibition. The derivatives with electron-withdrawing groups exhibited a better effect than those having electron-donating groups. The in silico experiments show that the ligands evaluated established interactions with the CAS site. This suggests that these compounds could be useful for generating better reversible and competitive inhibitors of AChE.
Guevara, Juan A.,Trujillo, José G.,Quintana, Delia,Jiménez, Hugo A.,Arellano, Mónica G.,Bahena, José R.,Tamay, Feliciano,Ciprés, Fabiola J.
p. 989 - 1003
(2017/12/18)

Alizarin red S-TiO2-catalyzed cascade C(sp3)-H to C(sp2)-H bond formation/cyclization reactions toward tetrahydroquinoline derivatives under visible light irradiation
A very low amount of organic dye (Alizarin red S) sensitized TiO2 and it was successfully used to catalyze cascade C(sp3)-H to C(sp2)-H bond formation/cyclization reactions under visible light irradiation. The modified TiO2 photocatalyst efficiently, for the first time, advanced [4+2] cyclization of N,N-dimethylanilines and maleimides to the corresponding tetrahydroquinolines in air atmosphere. The reaction proceeds through α-amino radicals without additional oxidant at ambient temperature to afford products in good to excellent yields.
Hosseini-Sarvari, Mona,Koohgard, Mehdi,Firoozi, Somayeh,Mohajeri, Afshan,Tavakolian, Hosein
supporting information
p. 6880 - 6888
(2018/05/04)

Three-Component Synthesis of Quinolines Based on Radical Cascade Visible-Light Photoredox Catalysis
Synthesis of highly substituted quinolines has been developed based on three-component radical cascade based on visible-light photoredox catalysis. This tandem coupling reaction has been coordinated to proceed with high chemoselectivity based on the differential electronic properties of coupling partners. Subjection of electron-rich β-aminoacrylates with electron-deficient halides and alkenes to the optimized conditions leads to the formation of quinolines in good yields after in situ oxidation of tetrahydroquinolines. Detailed mechanistic studies which reveal an unexpected reaction pathway is described. (Figure presented.).
Choi, Jun-Ho,Park, Cheol-Min
supporting information
p. 3553 - 3562
(2018/09/22)

Catalyst and Additive-Free Diastereoselective 1,3-Dipolar Cycloaddition of Quinolinium Imides with Olefins, Maleimides, and Benzynes: Direct Access to Fused N,N′-Heterocycles with Promising Activity against a Drug-Resistant Malaria Parasite
A convenient and eco-friendly synthesis of various fused N-heterocyclic compounds through catalyst and additive-free 1,3 dipolar cycloadditions of quinolinium imides with olefins, maleimides, and benzynes in excellent yields and diastereoselectivities is reported. The thermally controlled diastereoselective [3 + 2] cycloaddition reaction between quinolinium imides and olefins provided cis-isomers at low temperature and trans-isomers at high temperature. A reaction between quinolinium imides with substituted maleimides gave four-ring-fused N-heterocyclic compounds in high yields as a single diastereomer. The aryne precursors also provided four-ring-fused N,N′-heterocyclic compounds in high yields. The in vitro antiplasmodial activity of selected molecules revealed that this class of molecules possesses potential for ongoing studies against malaria.
Kumar, Rakesh,Chaudhary, Sandeep,Kumar, Rohit,Upadhyay, Pooja,Sahal, Dinkar,Sharma, Upendra
p. 11552 - 11570
(2018/09/25)

Solvent-free and room temperature visible light-induced C-H activation: CdS as a highly efficient photo-induced reusable nano-catalyst for the C-H functionalization cyclization of: T -amines and C-C double and triple bonds
Nano-sized CdS was successfully prepared, fully characterized and applied as a highly efficient reusable photocatalyst for the synthesis of pyrrolo[3,4-c]quinolone and pyrrolo[2,1-a]isoquinoline-8-carboxylate derivatives through a condensation reaction of N,N-dimethylanilines or alkyl 2-(3,4-dihydroisoquinolin-2(1H)-yl)acetates with maleimides via a C-H activation approach under benign and eco-friendly conditions at room temperature without using any solvent and oxidant under visible light irradiation. Besides, the prepared photocatalyst has been successfully applied for the condensation reaction of N,N-dimethylanilines with alkyl but-2-ynedioates or phenyl acetylenes for the synthesis of novel 1,2-dihydroquinoline-3,4-dicarboxylate and aryl-1,2-dihydroquinoline derivatives for the first time. Using this method, all favourable products were obtained in good yields and relatively short reaction times under benign conditions with the application of visible light irradiation, a renewable energy source. The catalyst was easily recovered and reused several times without any loss of its activity.
Firoozi, Somayeh,Hosseini-Sarvari, Mona,Koohgard, Mehdi
supporting information
p. 5540 - 5549
(2019/01/03)

Catalyzed preparation method of N-phenylmaleimide
The invention discloses a catalyzed preparation method of N-phenylmaleimide. The method is characterized by taking metalloporphyrin as a catalyst and enabling maleic anhydride to be reacted with aniline, wherein metalloporphyrin is mononuclear metalloporphyrin. The catalyzed preparation method of N-phenylmaleimide is a solvent-free method; organic solvent is not used as a water-carrying agent except the preparation raw materials; the cost is low; the catalyst is excellent in effect and is simple and easily available; the usage amount of the catalyst is extremely small and is only ppm-grade; the operation is simple; pressure-reduced distillation is directly carried out to obtain high-quality product without post-treatment after reaction is completed. The preparation method is environmentally friendly; the organic solvent is not used in reaction; the operations such as washing with water are not needed in post-treatment; the wastewater is not generated.
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Paragraph 0037-0051

(2019/01/07)

Cp?Co(III)-Catalyzed C-H Alkylation with Maleimides Using Weakly Coordinating Carbonyl Directing Groups
A novel protocol for ortho-C-H alkylation of aromatic and heteroaromatic ketones and esters under Cp?Co(III) catalysis has been developed for the first time. The reaction proceeds through initial cyclometalation via weak chelation-assisted C-H bond activation, followed by coordination of activated alkene, insertion between Co-C, and protodemetalation.
Mandal, Rajib,Emayavaramban, Balakumar,Sundararaju, Basker
supporting information
p. 2835 - 2838
(2018/05/29)

2. 3 - Naphthalenedicarboxylic acid imide derivative and its preparation method and application (by machine translation)
The invention provides a compound of formula I illustrated compound or isomer thereof or solvates or salts and its preparation method and application, the compounds of the HAUGLAND gram negative bacteria over-expression AcrB has better antibacterial synergistic activity and efflux inhibitory activity. (by machine translation)
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Paragraph 0112-0114

(2019/01/05)

Synthesis and Evaluation of Novel Spiro[oxindole-isoxazolidine] Derivatives as Potent Antioxidants
The antioxidant activity of isatin derivatives can be described with the presence of enolic hydroxyl group at the second position of the ring because of the keto-enol tautomerism between NH and C O groups of indolone moiety. The reducing ability of the tested compounds was evaluated by their interaction with the stable free radical 1,1-diphenyl-2-picrylhydrazyl (DPPH) at various concentrations. Novel spiro[oxindole-isoxazolidine] derivatives (4a, 4b, 4c, 4d, 4e, 4f, 4g, 4h, 4i) have been synthesized by 1,3-dipolar cycloaddition reactions of variously substituted maleimides (1) with isatin ketonitrone (3) and tested for their in vitro antioxidant potency in the DPPH assay. All the synthesized compounds have been identified as potent in vitro antioxidants.
Kaur, Manpreet,Singh, Baldev,Singh, Baljit,Arjuna, Anania
p. 1348 - 1354
(2017/03/27)

N-substituted benzal pyrrolidinedione and preparation method and application thereof
The invention discloses an N-substituted benzal pyrrolidinedione compound and a preparation method and application thereof. The N-substituted benzal pyrrolidinedione compound has very high tumor cell growth inhibition activity and particularly has a remarkable inhibition effect on growth of vascular endothelial growth factor receptor subtype 2 (VEGFR-2) high-expression human colon cancer cells (HCT116), the IC50 value of the N-substituted benzal pyrrolidinedione compound can reach 5.93 micromoles, and the N-substituted benzal pyrrolidinedione compound has an obvious inhibition effect on new vessel generation of chick embryos.
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Paragraph 0038

(2017/08/28)

Improvement of thermal properties of poly(vinyl chloride) using chemical blending assisted ultrasonic technique
The thermal stabilization of poly(vinyl chloride) through blending techniques has been studied. Poly(vinyl chloride) was blended with modified polymer (cellulose acetate-diallyl amine) in different compositions to improve the thermal stability of poly(vinyl chloride). The thermal stability and morphology of the blend films were characterized by scanning electron microscope (SEM) and thermogravimetry. The results revealed that the presence of modified cellulose acetate improved the thermal stability of poly(vinyl chloride). This was attributed to the thermal stable diallylamine moieties among the cellulose acetate chains. The addition of traces of maleimide derivatives to poly(vinyl chloride) prior to the blend process led to an extra thermal stability of the blend film as shown from the values of the initial decomposition temperature (To) measured by thermogravimetry.
Al-Ghamdi, Azza
p. 2285 - 2288
(2017/10/05)

Stable and Rapid Thiol Bioconjugation by Light-Triggered Thiomaleimide Ring Hydrolysis
Maleimide-mediated thiol-specific derivatization of biomolecules is one of the most efficacious bioconjugation approaches currently available. Alarmingly, however, recent work demonstrates that the resulting thiomaleimide conjugates are susceptible to breakdown via thiol exchange reactions. Herein, we report a new class of maleimides, namely o-CH2NHiPr phenyl maleimides, that undergo unprecedentedly rapid ring hydrolysis after thiol conjugation to form stable thiol exchange-resistant conjugates. Furthermore, we overcome the problem of low shelf lives of maleimide reagents owing to their propensity to undergo ring hydrolysis prior to bioconjugation by developing a photocaged version of this scaffold that resists ring hydrolysis. UV irradiation of thiol bioconjugates formed with this photocaged maleimide unleashes rapid thiomaleimide ring hydrolysis to yield the desired stable conjugates within 1 h under gentle, ice-cold conditions.
Kalia, Dimpy,Pawar, Sharad P.,Thopate, Jyoti S.
supporting information
p. 1885 - 1889
(2017/02/05)

Graphene Oxide as a Carbocatalyst for a Diels–Alder Reaction in an Aqueous Medium
The Diels–Alder (DA) reaction, a [4+2] cycloaddition reaction, is highly important in synthetic organic chemistry and is frequently used in the synthesis of natural products containing six-membered rings. Herein, we report an efficient protocol for the DA reaction between 9-hydroxymethylanthracene and N-substituted maleimides using two-dimensional graphene oxide (GO) as a heterogeneous carbocatalyst in an aqueous medium at room temperature. High yields, a wide substrate scope, low temperature, excellent functional group tolerance, atom economy, and water as a green solvent are noteworthy features of this protocol. The heterogeneous GO catalyst can be easily recovered and used multiple times without any significant loss in catalytic activity.
Girish, Yarabhally R.,Pandit, Subrata,Pandit, Subhendu,De, Mrinmoy
supporting information
p. 2393 - 2398
(2017/09/11)

Method for synthesizing N-phenylmaleimide and special catalyst for method
The invention discloses a synthesis method of N-phenylmaleimide (N-PMI). Under the action of a catalyst, the N-phenylmaleimide is directly synthesized by aniline and maleic anhydride in an organic solvent; the mass ratio of the organic solvent to maleic anhydride is (0.2-0.45) to 1; the mass ratio of aniline to maleic anhydride is (0.8-0.9) to 1; the reaction temperature is 135 DEG C-140 DEG C; and the reaction time is 0.8h-1h. By adopting the method provided by the invention, wastewater can be effectively reduced; and after the reaction is finished, the amount of acid remained in an N-PMI solution is few, so that the amount of water and alkali, which are used for water washing and neutralization in a post-treatment process, can be reduced. The synthesis method is a environment-friendly process route.
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Paragraph 0019; 0020; 0021; 0022; 0023; 0024; 0025; 0026

(2017/04/03)

N a one-step synthesis method of-phenyl maleimide
The invention relates to a one-step synthesis method of N-phenylmaleimide. The method comprises the following steps: adding organic acid or inorganic acid and a benzene solvent according to the volume ratio of 1:95-143 into a reactor, heating for dehydration, maintaining for 30-150 min to generate a mixed solvent; cooling, adding DMF and maleic anhydride, heating again, and dripping aniline within 40-150 min from below the liquid level after backflow of a liquid in the reactor so as to obtain a N-phenylmaleimide crude product; and processing the crude product to obtain a solid, namely N-phenylmaleimide. The method provided by the invention has advantages of low cost, high yield (which can reaches more than 90%), few process (one-step direct synthesis of N-PMI is adopted without the need of refining) and simple operation, is environmentally friendly, and is suitable for industrial production.
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Paragraph 0022; 0023; 0024; 0025

(2017/04/06)

Fluorene derivative and its preparation method
The invention discloses 1 and 4-disubstituted fluorene and synthesis of cyclic derivative thereof. A preparation method of fluorene derivative comprises the following steps: a precursor compound 1 and 3-bis(4-bromine phenyl)-2-acetone or 1 and 3-bis(2-bromine phenyl)-2-acetone and ninhydrin are reacted to synthesize indene cyclopentadiene ketone derivative; and then 1 and 4-disubstituted fluorene derivative generated by a molecular conjugated system is magnified through Diels-Alder cyclic addition. 9-oxo-1 and 4-bis(4-bromine phenyl) fluorene, 9-oxo-1 and 4-bis(2-bromine phenyl) fluorene or 2-phenyl-4, 10-bis(4-bromine phenyl)-fluorene[1 and 2-f] isobenzazole-1, 3 and 5-triketone and 2- thiophene boric acid are reacted through the Suzuki reaction to generate the fluorene derivative containing terminated thiophene. As the fluorine derivative has good heat stability, the novel possibility is provided for exploring novel organic electroluminescence and solar cell materials.
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Paragraph 0068; 0069; 0070

(2016/10/07)

Photoorganocatalysed and visible light photoredox catalysed trifluoromethylation of olefins and (hetero)aromatics in batch and continuous flow
Trifluoromethylation of olefins and (hetero)aromatics with sodium triflinate as CF3 source and readily accessible benzophenone derivatives as photosensitisers has been developed in batch and flow. The use of an iridium-based photocatalyst enables the trifluoromethylation to proceed under visible light irradiation.
Lefebvre, Quentin,Hoffmann, Norbert,Rueping, Magnus
supporting information
p. 2493 - 2496
(2016/02/18)

Pyrazole-type N-phenyl maleimide derivative with chromone structure, and preparation method and application thereof
The invention discloses 3-(6-bromine-4-oxygen-4H-chromone)-1, 5-diphenyl-1, 6a-dihydrogen pyrroline [3, 4-c] pyrazole-4, 6 (3aH, 5H)-diketone, and a preparation method and application thereof. According to the preparation method, a pyrazole ring is introduced into an n-replaced phenyl maleimide structure according to a 1, 3-dipole cycloaddition method, the chromone structure is imported after reaction between the pyrazole ring and a chromone derivate, and accordingly, the novel 3-(6-bromine-4-oxygen-4H-chromone)-1, 5-diphenyl-1, 6a-dihydrogen pyrroline [3, 4-c] pyrazole-4, 6 (3aH, 5H)-diketone is compounded. The compound has good inhibition effect on tumor cell strains, has higher inhibition ratio and selectivity for oral cavity cancer cells, and has good industrial application prospect in preparation of antineoplastic drugs and the like.
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Paragraph 0014; 0029; 0030

(2017/01/26)

Identification of an anti-inflammatory derivative with anti-cancer potential: The impact of each of its structural components on inflammatory responses in macrophages and bladder cancer cells
Inflammation plays a crucial role in many types of cancer and is known to be involved in their initiation and promotion. As such, it is presently recognized as an important risk factor for several types of cancers such as bladder, prostate and breast cancers. The discovery of novel anti-inflammatory compounds can have a huge implication not only for the treatment of cancer but also as preventive and protective treatment modalities. We have recently identified a new compound (1) that presents interesting anti-inflammatory activity. In order to better understand its biological action, we have divided the molecule in its basic components and verified their respective contribution towards the anti-inflammatory response of the whole molecule. We have discovered that only the combination of the maleimide function together with the tert-butyloxycarbonylhydrazinamide function lead to important anti-inflammatory properties. The main derivative 1 can decrease the activating effects of INFγ or IL6 on human (hMωs) macrophages by 38% or by 64% at a concentration of 10 μM as indicated by a decrease of STAT1 or STAT3 activation. The expression of pro-inflammatory markers CD40 and MHCII in INFγ stimulated hMωs were reduced by 87% and 49%, respectively with a 3 h pretreatment of 1 at 10 μM. The cell motility assay revealed that 1 at 10 μM can reduce relative cell motility induced by IL6 by 92% in comparison with the untreated control hMω monolayers. Compound 1 reduced by 91% the inflammatory response induced by the cytokines (INFγ + TNFα) in the macrophage-like J774A.1 cells at a concentration of 25 μM, as measured by the detection of NO production with the Griess reagent. Furthermore, upon removal of the tert-butyloxycarbonyl protective group the unprotected derivative as a hydrochloride salt (1A) retains interesting anti-inflammatory activity and was found to be less toxic than the parent compound (1).
Hamelin-Morrissette, Jovane,Cloutier, Suzie,Girouard, Julie,Belgorosky, Denise,Eiján, Ana María,Legault, Jean,Reyes-Moreno, Carlos,Bérubé, Gervais
p. 259 - 268
(2015/04/27)

DABCO-catalyzed [3+2] cycloaddition reactions of azomethine imines with N-aryl maleimides: Facile access to dinitrogen-fused heterocycles
DABCO-catalyzed [3+2] cycloaddition of azomethine imines with maleimides has been developed. This method could efficiently furnish dinitrogen-fused tetracyclic heterocycles in high levels of regioselectivity and with good yields.
Jia, Qianfa,Chen, Lei,Yang, Gongming,Wang, Jian,Wei, Jia,Du, Zhiyun
supporting information
p. 7150 - 7153
(2015/12/12)

Radical-mediated dehydrative preparation of cyclic imides using (NH4)2S2O8-DMSO: Application to the synthesis of vernakalant
Ammonium persulfate-dimethyl sulfoxide (APS-DMSO) has been developed as an efficient and new dehydrating reagent for a convenient one-pot process for the synthesis of miscellaneous cyclic imides in high yields starting from readily available primary amines and cyclic anhydrides. A plausible radical mechanism involving DMSO has been proposed. The application of this facile one-pot imide forming process has been demonstrated for a practical synthesis of vernakalant.
Garad, Dnyaneshwar N.,Tanpure, Subhash D.,Mhaske, Santosh B.
supporting information
p. 1008 - 1016
(2015/08/18)

Visible light mediated cyclization of tertiary anilines with maleimides using nickel(II) oxide surface-modified titanium dioxide catalyst
Surface-modified titanium dioxides by highly dispersed NiO particles have an extended absorption in the visible light region and a reduced hole-electron pair recombination than unmodified TiO2. They have now been successfully applied as highly active heterogeneous photocatalysts in the visible light mediated direct cyclization of tertiary anilines with maleimides to give tetrahydroquinoline products in moderate to high yields at ambient temperature. In contrast with unmodified titanium dioxide catalysts that are conventionally used in a stoichiometric amount in combination with UVA light, only a catalytic amount (1 mol %) of the surface-modified TiO2 catalyst is needed along with visible light to efficiently catalyze the reaction. Compared with transition-metal complexes such as Ru(bpy)3Cl2 or Ir(ppy)2(dtbbpy)PF6, advantages of these surface-modified titanium dioxides as photocatalyst include high catalytic activity, low cost, ease of recovering, and being able to be used for at least nine times without significant decay of catalytic activity.
Tang, Jian,Grampp, Günter,Liu, Yun,Wang, Bing-Xiang,Tao, Fei-Fei,Wang, Li-Jun,Liang, Xue-Zheng,Xiao, Hui-Quan,Shen, Yong-Miao
supporting information
p. 2724 - 2732
(2015/03/18)

Study of the diels-alder and retro-diels-alder reaction between furan derivatives and maleimide for the creation of new materials
The Diels-Alder reaction leads to a mixture of two diastereomers, one called endo and the other one exo. The cyclo-reversion temperature of the first one is lower than the exo adduct and the ratio between endo and exo adducts varies according to the substituents of the Diels-Alder partners and experimental parameters. Therefore, the influence of some reaction parameters such as the substituents of furan and maleimide derivatives, the reaction temperature and the presence of a nucleophile on the endo/exo Diels-Alder ratio and/or the retro-Diels-Alder reaction have been studied. For instance, furan and maleimide derivatives with electron withdrawing substituents induced the creation of the endo adduct preferentially. Also the presence of a far electron withdrawing substituent on furan and/or an electron attracting mesomeric substituent on maleimide resulted in a faster reversibility of the endo adduct. Finally, a high temperature and the presence of a nucleophile (thiol) also induced faster retro-Diels-Alder kinetics. Moreover, it was proved that isomerization from the endo to the exo diastereomer is preceded by a retro-Diels-Alder reaction of the endo adduct. The presence of a nucleophile in the mixture confirmed this result. This study allowed the highlighting of different parameters of the Diels-Alder reaction to obtain as much endo adduct as possible, and a fast and/or full retro-Diels-Alder reaction of this adduct.
Froidevaux,Borne,Laborbe,Auvergne,Gandini,Boutevin
p. 37742 - 37754
(2015/05/13)

Polyethylene as a Cosolvent and Catalyst Support in Ring-Opening Metathesis Polymerization
Polyethylene oligomers (PEOlig) can be used as cosolvents and sometimes soluble catalyst supports in ring-opening metathesis polymerization (ROMP) reactions. As a catalyst support, this polyolefin serves as an N-heterocyclic carbene ligand for a ROMP catalyst, making it soluble at 70 °C and insoluble at room temperature. As a cosolvent, unfunctionalized PE oligomers facilitate quantitative separation of PEOlig-bound Ru-catalyst residues from polymer products. In these cases, the insolubility of the unfunctionalized polyethylene (Polywax) and its entrapment of the PEOlig-supported Ru residue in the product phase at room temperature afford ROMP products with Ru contamination lower than other procedures that use soluble catalysts. These separations require only physical processes to separate the product and catalyst residues - no additional solvents are necessary. Control experiments suggest that most (ca. 90%) of the Ru leaching that is seen results from Ru byproducts formed in the vinyl ether quenching step and not from the polymerization processes involving the PEOlig-supported Ru complex. (Chemical Equation Presented).
Suriboot, Jakkrit,Hobbs, Christopher E.,Guzman, William,Bazzi, Hassan S.,Bergbreiter, David E.
p. 5511 - 5516
(2015/09/02)

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)

Unusual regio- and stereo-selectivity in Diels-Alder reactions between bulky N-phenylmaleimides and anthracene derivatives
Unusual regio- and stereo-selectivity in Diels-Alder (D-A) reactions were achieved between bulky N-phenylmaleimides and anthracene derivatives. Using multiple substituents with steric hindrance on both diene and dienophile, a noticeable shift toward 1,4-addition was successfully obtained. The substrate scope in this reaction was broad and the highest yield of anti-1,4-adducts was over 90%. Novel structures of anti-1,4-adducts were confirmed by single crystal X-ray diffraction analysis. This study not only provides the first reported method of synthesizing anti-1,4-adducts and achieving otherwise unattainable regio- and stereo-selectivity, but also elucidates the importance of combining the steric effects of two reactants to shift products toward 1,4-adducts. Moreover, the resulting 1,4-adducts could be further functionalized through their halogen groups via carbon-carbon coupling reactions.
Chen, Hao,Yao, Erdong,Xu, Chi,Meng, Xiao,Ma, Yuguo
supporting information
p. 5102 - 5107
(2014/07/08)

Synthesis and biological evaluation of novel N-aryl maleimide derivatives clubbed with α-hydroxyphosphonates
A series of novel molecules 5a-g containing N-aryl maleimide and α-hydroxyphosphonate moieties were synthesized. A distinct approach for high-yielding synthesis of α-hydroxyphosphonates has been discovered using various catalyst and solvents. The structures of the synthesized compounds were elucidated by IR, NMR, MS and CHN analysis. All the synthesized compounds were tested for qualitative (Zone of inhibition) and quantitative (MIC) antimicrobial activities against two pathogenic bacteria such as Bacillus subtilis (NCIM 2250) and Escherichia coli (ATCC 25922) and four pathogenic fungi such as Candida albicans (MTCC 277), Candida tropicalis (MTCC184), Aspergillus niger (MCIM 545) and Aspergillus clavatus (MTCC 132). The investigation of antimicrobial screening data revealed that most of the tested compounds are moderate to good microbial inhibitors.
Patil, Nilesh S.,Deshmukh, Ganesh B.,Patil, Sambhaji V.,Bholay, Avinash D.,Gaikwad, Nitin D.
p. 490 - 497
(2014/07/21)

Phosphine-catalyzed [4+1] annulation of 1,3-(aza)dienes with maleimides: Highly efficient construction of azaspiro[4.4]nonenes
Phosphine-catalyzed [4+1] annulation of electron-deficient 1,3-dienes or 1,3-azadienes with maleimides has been successfully developed under very mild conditions, providing a convenient and highly efficient method for constructing 2-azaspiro[4.4]nonenes and 1,7-diazaspiro[4.4]nonenes. This reaction represents the first example of [4+1] cyclization between electron-deficient 4π-conjugated systems and non-allylic phosphorus ylides.
Yang, Mei,Wang, Tianyi,Cao, Shixuan,He, Zhengjie
supporting information
p. 13506 - 13509
(2015/01/09)

Synthesis of Diels-Alder adducts of the quinolizidine alkaloids N-methylcytisine, (-)-leontidine, and (-)-thermopsine with N-phenylmaleimide
The Diels-Alder adducts of the quinolizidine alkaloids N-methylcytisine, (-)-leontidine, and (-)-thermopsine with N-phenylmaleimide have been synthesized. The structures and absolute configurations of the new asymmetric centers of the products were determ
Tsypysheva, Inna P.,Lobov, Alexander N.,Kovalskaya, Alena V.,Vinogradova, Valentina I.,Suponitsky, Kyrill Yu.,Khursan, Sergey L.,Yunusov, Marat S.
p. 1318 - 1323
(2013/11/19)

Synthesis and evaluation of novel 2,3,5-triaryl-4H,2,3,3a,5,6,6a- hexahydropyrrolo[3,4-d]isoxazole-4,6-diones for advanced glycation end product formation inhibitory activity
The synthesis of some biologically interesting pyrrolo-isoxazolidine derivatives was accomplished by the 1,3-dipolar cycloaddition reaction of substituted azomethine N-oxides 1 with substituted N-aryl maleimides 2 leading to the formation of new stereoisomeric 2,3,5-triaryl-4H,2,3,3a,5,6,6a- hexahydropyrrolo[3,4-d]isoxazole-4,6-dione derivatives 3 in excellent yields. The synthesized compounds have been screened for their advanced glycation end (AGE) product formation inhibitory activity on the basis of their ability to inhibit the formation of AGEs in the bovine serum albumin (BSA)-glucose assay. All the synthesized compounds have been found to exhibit significant activity against AGE formation.
Kaur, Anjandeep,Singh, Baldev,Jaggi, Amteshwar Singh
supporting information
p. 797 - 801
(2013/02/25)

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)

Solvent-mediated one-pot synthesis of cyclic N-Substituted imides
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Patil, Sambhaji V.,Mahale, Keshao A.,Gosavi, Kirankumar S.,Deshmukh, Ganesh B.,Patil, Nilesh S.
p. 314 - 320
(2013/07/26)

Porous material-immobilized iodo-Bodipy as an efficient photocatalyst for photoredox catalytic organic reaction to prepare pyrrolo[2,1-a]isoquinoline
Iodo-Bodipy immobilized on porous silica was used as an efficient recyclable photocatalyst for photoredox catalytic tandem oxidation-[3+2] cycloaddition reactions of tetrahydroisoquinoline with N-phenylmaleimides to prepare pyrrolo[2,1-a]isoquinoline.
Guo, Song,Zhang, Hongli,Huang, Ling,Guo, Zhendong,Xiong, Guang,Zhao, Jianzhang
supporting information
p. 8689 - 8691
(2013/09/23)

Iridium-catalyzed asymmetric hydrogenation of α-alkylidene succinimides
Not to be out PhOXed! The title reaction provides a new approach to chiral succinimide derivatives with excellent yields and ee values by using a low catalyst loading (0.05 mol %) and mild reaction conditions. Chiral 3-benzyl pyrrolidines and 1-hydroxypyrrolidine-2,5-diones, important structural motifs in natural products and pharmaceuticals, could be readily prepared. BARF -=tetrakis[3,5-bis(trifluoromethyl)phenyl]borate. Copyright
Liu, Yuanyuan,Zhang, Wanbin
supporting information
p. 2203 - 2206
(2013/03/28)

C60-Bodipy dyad triplet photosensitizers as organic photocatalysts for photocatalytic tandem oxidation/[3+2] cycloaddition reactions to prepare pyrrolo[2,1-a]isoquinoline
C60-Bodipy hybrids exhibiting strong absorption of visible light and long-lived triplet excited states were used as photocatalysts for tandem oxidation/[3+2] cycloaddition of tetrahydroisoquinoline with N-phenylmaleimide to produce pyrrolo[2,1-a]isoquinolines. The reaction is substantially accelerated, compared to that catalyzed by Ru(bpy)3Cl2.
Huang, Ling,Zhao, Jianzhang
supporting information
p. 3751 - 3753
(2013/05/22)