- Maleimide-based metal-free ligation with dienes: A comparative study
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A brief literature survey reveals that metal-free ligation such as the maleimide-based cycloaddition with electron-rich (hetero)dienes is a widespread tool for the assembly of (bio)molecular systems with applications in biotechnology, materials science, polymers and bio-organic chemistry. Despite their everyday use, only scattered data about their kinetics as well as the stabilities of corresponding products under physiological conditions, are accessible. These key parameters are yet, of paramount importance to ensure the rapid and effective preparation of stable compounds. Herein is reported a systematic study regarding the different classes of dienes used in chemoselective ligation, including their accessibility and stability, as well as comparative kinetic experiments and products stability assays. We took advantage of these data to develop a double labeling strategy from the combined use of cyclopentadiene and oxazole dienes.
- Bailly, Laetitia,Frisby, Axel,Le Nahenec-Martel, Patricia,Lossouarn, Alexis,Renard, Pierre-Yves,Renault, Kévin,Sabot, Cyrille
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p. 3874 - 3887
(2020/06/03)
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- Cp?Co(III)-Catalyzed C-H Alkylation with Maleimides Using Weakly Coordinating Carbonyl Directing Groups
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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
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supporting information
p. 2835 - 2838
(2018/05/29)
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- Synthesis and biological evaluation of novel pyrrolidine acid analogs as potent dual PPARα/γ agonists
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The design, synthesis and structure-activity relationships of a novel series of 3,4-disubstituted pyrrolidine acid analogs as PPAR ligands is outlined. In both the 1,3- and 1,4-oxybenzyl pyrrolidine acid series, the preferred stereochemistry was shown to be the cis-3R,4S isomer, as exemplified by the potent dual PPARα/γ agonists 3k and 4i. The N-4-trifluoromethyl-pyrimidinyl pyrrolidine acid analog 4i was efficacious in lowering fasting glucose and triglyceride levels in diabetic db/db mice.
- Zhang, Hao,Ding, Charles Z.,Lai, Zhi,Chen, Sean S.,Devasthale, Pratik,Herpin, Tim,Morton, George,Qu, Fucheng,Ryono, Denis,Smirk, Rebecca,Wang, Wei,Wu, Shung,Ye, Xiang-Xang,Li, Yi-Xin,Apedo, Atsu,Farrelly, Dennis,Wang, Tao,Gu, Liqun,Morgan, Nathan,Flynn, Neil,Chu, Cuixia,Kunselman, Lori,Lippy, Jonathan,Locke, Kenneth,O'Malley, Kevin,Harrity, Thomas,Cap, Michael,Zhang, Lisa,Hosagrahara, Vinayak,Kadiyala, Pathanjali,Xu, Carrie,Doweyko, Arthur M.,Zahler, Robert,Hariharan, Narayanan,Cheng, Peter T.W.
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p. 1196 - 1205
(2015/04/27)
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- An unexpected formation of the novel 7-oxa-2-azabicyclo[2.2.1]hept-5-ene skeleton during the reaction of furfurylamine with maleimides and their bioprospection using a zebrafish embryo model
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An unexpected intramolecular cyclization during the reaction of furfurylamine with maleimides is reported as a novel strategy for the efficient green synthesis of the 7-oxa-2-azabicyclo[2.2.1]hept-5-ene skeleton. Under the same reaction conditions, 7-oxabicyclo[2.2.1]hept-5-enes were synthesized when furfurylamine was N-protected by the acetyl group. Both types of bicycloheptenes were screened using the zebrafish model system for genetics and developmental biology. The Royal Society of Chemistry 2013.
- Puerto Galvis, Carlos E.,Kouznetsov, Vladimir V.
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supporting information
p. 407 - 411
(2013/02/25)
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- Heat-resistant poly(N-(1-phenylethyl)maleimide-co-styrene) microspheres prepared by dispersion polymerization
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This article reports on a novel type of polymeric microsphere consisting of poly(N-(1-phenylethyl)maleimide-co-styrene) (poly(N-PEMI-co-St)) and showing remarkable heat resistance. Such microspheres were prepared by dispersion polymerization with 2,2′-azo
- Tong, Linyue,Cui, Xin,Yang, Wantai,Deng, Jianping
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supporting information; experimental part
p. 6697 - 6703
(2012/08/08)
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- Synthesis and stereochemistry of some novel dihydropyrrolo[3,4-c]pyrazoles
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Eleven novel dihydropyrrolo[3,4-c]pyrazole derivatives were obtained by the reaction of chiral (1R)-N-(1-phenylethyl)maleimide and C,N-aryl-substituted nitril-imines. The reaction afforded the cycloadducts as a regioisomeric mixture which can be separable in some cases. The structure and stereochemistry of cycloadducts were assigned on the basis of infrared (IR), 1H and 13C nuclear magnetic resonance (NMR), mass and X-ray spectra, optical rotation measurements, and CHN analyses.
- Dueruest, Yasar,Yildirm, Muhammet,Fronczek, Chris F.,Fronczek, Frank R.
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experimental part
p. 127 - 138
(2012/07/27)
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- A facile synthesis of N-substituted maleimides
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A simple and efficient method for the synthesis of N-substituted maleimides from the corresponding maleamic acids under the phase transfer catalysis has been described.
- Deshpande, Sunita R.,Maybhate, Shailaja P.,Likhite, Anjali P.,Chaudhary, Preeti M.
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experimental part
p. 487 - 488
(2010/10/18)
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- A flexible approach to methyl (5S)-5-alkyltetramate derivatives
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Regioselective Grignard reagent additions to 3-methoxymaleimides and subsequent diastereoselective reductive dehydroxylation of the resulting N,O-acetals were studied. On the basis of these studies, a flexible and highly regio- and diastereoselective approach to methyl 5-alkyltetramate derivatives was disclosed. The method is the first direct and flexible asymmetric cationic synthon-based approach, and allows for the synthesis of various methyl (5S)-5-alkyltetramate derivatives that are otherwise inaccessible by the commonly used methods based on α-amino acids. Georg Thieme Verlag Stuttgart.
- Jiang, Li-Jiao,Lan, Hong-Qiao,Zheng, Jian-Feng,Ye, Jian-Liang,Huang, Pei-Qiang
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scheme or table
p. 297 - 301
(2009/06/25)
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- Base-induced alcoholysis of N-arylmaleimides: Facile in situ oxa-Michael addition to alkyl maleanilates: Two-step one-pot rapid access to alkoxysuccinic acids
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A simple, efficient and general two-step, one-pot approach to alkoxysuccinic acids is described. The potassium carbonate-catalyzed reactions of alcohols with N-p-tolylmaleimide (4) followed by an acid-induced hydrolysis of intermediate products furnished alkoxysuccinic acids 1a-f in 90-98% yields. All the intermediates from the reaction of imide 4 with alcohols have been isolated and characterized, proving that the in situ formed alkyl maleanilates 3 are the actual Michael acceptors.
- Mhaske, Santosh B.,Argade, Narshinha P.
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p. 863 - 870
(2007/10/03)
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- Synthesis and reactivity of (1S)-N-(1-phenylethyl)maleimide towards nucleophiles: An application to preparation of chiral pyrroloisothiochroman and pyrrolobenzo[d]thiepine based on π-cationic cyclization
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Chiral pyrroloisothiochroman and pyrrolo[d]thiepine were obtained efficiently in four steps from N-alkylated maleimides via, successively, sulfurization, regioselective reduction followed by π-cationic cyclization of the N-acyliminium ion intermediates. These latter, in addition, led to conjugate enamides as a consequences of the dehydration reaction.
- Chihab-Eddine, Abderrahim,Dach, Adam,Jilale, Abderrahim,Decroix, Bernard
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p. 573 - 576
(2007/10/03)
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- Solvent free N-alkyl and N-arylimides preparation from anhydrides catalyzed by TaCl5-silica gel
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The first Lewis acid catalyzed and solvent free procedure for the preparation of imides from the corresponding anhydrides is described involving TaCl5-silica gel as Lewis acid under microwave irradiation.
- Chandrasekhar,Takhi, Mohamed,Uma
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p. 8089 - 8092
(2007/10/03)
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- Asymmetric cycloaddition of anthrone with n-substituted maleimides with C2-chiral pyrrolidines
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Base-catalyzed asymmetric cycloaddition of anthrone with achiral and chiral N-substituted maleimides was carried out in the presence of C2-chiral pyrrolidines in almost quantitative yields. Chiral, non-racemic [4+2] adducts up to 61% ee were produced with achiral N-methyl and N-benzylmaleimide using the chiral catalysts. De's of the adducts up to 38% were observed in the cases of chiral N-substituted maleimides and achiral pyrrolidine, in which the absolute configuration Of the major product was established by X-ray analysis. The combination of chiral maleimides and chiral catalysts afforded the adducts having up to 80% de.
- Tokioka, Kyohei,Masuda, Satoshi,Fujii, Tomomi,Hata, Yasuo,Yamamoto, Yukio
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p. 101 - 107
(2007/10/03)
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- Use of readily available monomers in the synthesis of vinyl copolymers with optical activity arising from the configuration of stereogenic carbon atoms in the main chain
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The present work was aimed at synthesising vinyl copolymers with optical activity arising only from the configuration of the stereogenic carbon atoms in the main chain. By copolymerising optically active diesters of fumaric acid with styrene, backbones wi
- Donnelly, Irene H.,Kambouris, Peter,Nonhebel, Derek C.,Rohr, Thomas,Sherrington, David C.
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p. 1821 - 1829
(2007/10/03)
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- Method for preparing homochiral maleimide intermediates, via silylation techniques
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A method is provided for preparing homochiral maleimide intermediates of the structure STR1 wherein R7, R8 and R9 are as defined herein by reacting a homochiral amine of the structure STR2 with maleic anhydride and a silylating agent. The maleimide intermediate is used in the enantio-selective preparation of thromboxane A2 receptor antagonists.
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- 7-oxabicycloheptane carboxylic acid prostaglandin analog intermediates useful in the preparation of anti-thrombotic and anti-vasospastic compounds and method for preparing same
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A method is provided for preparing carboxylic acid intermediates of the structure STR1 wherein an aldehyde of the structure STR2 is prepared and subjected to a Horner-Emmons reaction to form the ester of the structure STR3 and the ester is hydrogenated to the carboxylic acid which may be used in making the final anti-thrombotic--anti-vasospastic compounds.
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- Diastereoselective Diels-Alder reactions between substituted 1,3-butadienes and N-α-methylbenzylmaleimide
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The TiCl4 catalyzed reaction between 2-t-butyl-1,3-butadiene and N-α-methylbenzylmaleimide at -65°C affords diastereomeric Diels-Alder adducts in a 15:1 ratio. The structure of the major adduct was determined by x-ray.
- Baldwin,Greenspan,Alaimo,McPhail
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p. 5877 - 5880
(2007/10/02)
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- Synthesis of N-Aryl/heteroaryl/-substituted-methyl-&α-(p-substituted anilino)succinimides as Antituberculosis Agents
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A series of N-Aryl/heteroaryl/substituted-methyl-α-(p-substituted anilino)succinimides (II) have been prepared and screened in vitro against H37Rv strain of Mycobacterium tuberculosis.Some of these compounds exhibit activity upto 0.39 μg/ml concentration.
- Rangnekar, V. M.,Bhamaria, R. P.,Khadse, B. G.
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p. 342 - 344
(2007/10/02)
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- Synthesis of N-Aryl/substituted-methyl/heteroaryl-&α-pyrrolidino/piperidino Succinimides as Antituberculosis Agents
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A series of N-Aryl/substituted-methyl/heteroaryl-α-pyrrolidino- and piperidino-succinimides (II) have been prepared and screened in vitro against H37Rv strain of Mycobacterium tuberculosis.Some of these compounds exhibit activity upto 1.56 μg/ml concentration.
- Rangnekar, V. M.,Lokhande, S. R.,Bhamaria, R. P.,Khadse, B. G.
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p. 1070 - 1071
(2007/10/02)
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