- Extending the chemical product tree: A novel value chain for the production of: N -vinyl-2-pyrrolidones from biogenic acids
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The sustainable production of polymers from biogenic platform chemicals shows great promise to reduce the chemical industry's dependence on fossil resources. In this context, we propose a new two-step process leading from dicarboxylic acids, such as succinic and itaconic acid, to N-vinyl-2-pyrrolidone monomers. Firstly, the biogenic acid is reacted with ethanolamine and hydrogen using small amounts of water as solvent together with solid catalysts. For effective conversion, the optimal catalyst (carbon supported ruthenium) has to hold the ability of activating H2 as well as (imide) CO bonds. The obtained products, N-(2-hydroxyethyl)-2-pyrrolidones, are subsequently converted in a continuous gas phase dehydration over simple sodium-doped silica, with excellent selectivity of above 96 mol% and water as the sole by-product. With a final product yield of ≥72 mol% over two process steps and very little waste due to the use of heterogeneous catalysis, the proposed route appears promising-commercially as well as in terms of Green Chemistry.
- Haus, Moritz Otto,Louven, Yannik,Palkovits, Regina
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- A NEW SYTHESIS AND CRYSTAL STRUCTURE OF N-(2-HYDROXYETHYL)SUCCINIMIDE
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N-(2-hydroxyethyl)succinimide was formed with 80percent yield in the reaction of 2-oxazolidinone with succinic anhydride at 210 deg C instead of polyesteramides obtained from N-substituted 2-oxazolidinones.The identification based on the crystal structure
- Pitkanen, Maija,Pitkanen, Ilkka,Eriksson, Hans-Erik,Autio, Pekka
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- A procedure for preparing N-hydroxyethyl-substituted succinimide and phthalimide
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Conditions of synthesis of N-hydroxyethyl-substituted succinimide and phthalimide by reactions of dicarboxylic acid imides with aminoethanol were optimized.
- Gasanov,Allakhverdiev
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- PROCESS FOR PREPARATION OF DIROXIMEL FUMARATE
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The present invention relates to a process for the preparation of diroximel fumarate, a compound of formula I. The present invention relates to amorphous solid dispersion comprising diroximel fumarate, a compound of formula I or salt thereof together with at least one pharmaceutically acceptable carrier and process for its preparation.
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Paragraph 0144
(2021/04/01)
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- IMPROVED PROCESS FOR THE PREPARATION OF DIROXIMEL FUMARATE AND SOLID FORMS THEREOF
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Aspects of the present application relate to crystalline and amorphous solid forms of Diroximel fumarate, pharmaceutical compositions and processes thereof. Further, aspects relate to improved processes for the preparation of Diroximel fumarate and interm
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Page/Page column 22; 23
(2021/04/23)
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- Facile synthesis of indolizinoindolone, indolylepoxypyrrolooxazole, indolylpyrrolooxazolone and isoindolopyrazinoindolone heterocycles from indole and imide derivatives
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Chemo-, regio- and diastereoselective coupling reactions of indole with imide derivatives leading to unique heterocyclic systems are demonstrated. Acid-induced 3-position coupling reactions of indole with cyclic imide derived lactamols followed by acid promoted 2-position cyclizations with the corresponding aldehydes are described to obtain the indolizinoindolones and benzoindolizinoindolones. Base induced 2-position coupling reactions ofN-tosylindole withN-(2-iodoethyl)imides and the subsequent cyclizations provide indolylepoxypyrrolooxazole, indolylpyrrolooxazolone and indolyloxazoloisoindolone. Reductive cleavage of indolyloxazoloisoindolone to the corresponding alcohol followed by mesylation and base promotedN-cyclization affords thein situair-oxidized pentacyclic product hydroxyisoindolopyrazinoindolone. A regioisomeric structural revision of the natural product from 1,2,5,6,7,11c-hexahydro-3H-indolizino[7,8-b]indol-3-one to 1,2,5,6,11,11b-hexahydro-3H-indolizino(8,7-b)indol-3-one is also reported in the present studies focussed on the methodologies for heterocyclic synthesis.
- Argade, Narshinha P.,Shelar, Santosh V.
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p. 6160 - 6169
(2021/07/21)
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- METHOD FOR PRODUCING MONOMETHYL FUMARATE COMPOUNDS
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The present invention relates to a novel method for preparing monomethyl fumarate, which can preferably be used in the treatment and/or prevention of systemic diseases, autoimmune diseases, inflammatory diseases such as multiple sclerosis and psoriasis. Further, the present invention relates to the use of specific compounds as intermediates in the process for preparing a monomethyl fumarate prodrug.
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Page/Page column 41; 42; 44; 45; 46
(2017/07/14)
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- Transition State-Based Sialyltransferase Inhibitors: Mimicking Oxocarbenium Ion by Simple Amide
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In the new transition-state based sialyltransferase inhibitors, an amide group was placed at the corresponding C-2 position of CMP-sialic acid to mimic the geometry and charge distribution in the transition state, and simple aromatic or aliphatic rings were used instead of the sialic acid moiety. All synthetic compounds exhibited excellent α(2-6)-sialyltransferase inhibition, resulting in up to a 2600-fold higher affinity for the enzyme than CMP-Neu5Ac, suggesting that amide is a key element for simulating transition-state features.
- Guo, Jian,Li, Wenming,Xue, Weiwei,Ye, Xin-Shan
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supporting information
p. 2135 - 2141
(2017/03/17)
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- Process for production of cyclic N-vinyl carboxylic acid amide
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There is provided a process for producing a cyclic N-vinyl carboxylic acid amide stably in safety and low cost, using, as starting raw materials, a cyclic carboxylic acid ester and monoethanolamine both available inexpensively and easily. The process comprises subjecting a cyclic carboxylic acid ester and monoethanolamine to an intermolecular dehydration reaction (a first-step reaction) in a liquid phase to produce a cyclic N-(2-hydroxyethyl) carboxylic acid amide and then subjecting the cyclic N-(2-hydroxyethyl) carboxylic acid amide to an intramolecular dehydration reaction (a second-step reaction) in a gas phase in the presence of an oxide catalyst containing an alkali metal element and/or an alkaline earth metal element and silicon, to produce a cyclic N-vinyl carboxylic acid amide.
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- Attempted synthesis of substituted 8-oxo-4-oxa-1-azabicyclooctane through intramolecular reductive cyclisation
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Reductive intramolecular cyclisation of 2-(N-succinimido)-1-ethanol gives 8-oxo-4-oxa-1-azabicyclooctane in a good yield.On introduction of further substitution of C-1 and C-2 no cyclisation is observed.A mechanistic rational is presented.
- Mishra, Shri Krishna,Vani, T R,Rao, R Balaji
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p. 641 - 644
(2007/10/02)
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- DIASTEREOSELECTIVE ALKYLATION OF CHIRAL TIN(II) ENOLATES ONTO CYCLIC ACYL IMINIUM IONS. ASYMMETRIC TOTAL SYNTHESIS OF (-)-SUPINIDINE
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The scope and mechanism of the asymmetric alkylation of chiral tin(II) enolate 10 with cyclic acyl iminium ion 5 were investigated.An application of the reaction to the asymmetric synthesis of (-)-supinidine was also achieved.
- Nagao, Yoshimitsu,Dai, Wei-Min,Ochiai, Masahito,Shiro, Motoo
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p. 6361 - 6380
(2007/10/02)
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- NEW CHIRAL RECOGNITION OF CHIRAL TIN(II) ENOLATES TOWARD CYCLIC ACYL IMINIUM SPECIES. ASYMMETRIC TOTAL SYNTHESIS OF (-)-SUPINIDINE
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Diastereoselective alkylation of chiral tin(II) enolates 1 onto cyclic acyl iminium ion 7 proceeded in a different chiral recognition mode from the case of 1 onto cyclic acyl imines 3.This new diastereoselective alkylation was efficiently utilized for an asymmetric total synthesis of (-)-supinidine (20).
- Nagao, Yoshimitsu,Dai, Wei-Min,Ochiai, Masahito
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p. 6133 - 6136
(2007/10/02)
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