- Studies on the carbenium-iminium ions derived from N-methylmorpholine-N- oxide (NMMO)
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Two carbenium-iminium ions, an exo-centered species 2 and a ring-centered form 3, are derived from the widely used oxidant and cellulose solvent N-methylmorpholine-N-oxide (1) by heterolytic degradation. 3 rearranges into 2 in the presence of water, in an endothermic, bimolecular reaction involving a highly organized transition state, which is the first example of a carbenium-iminium ion interconversion. The reaction mechanism was investigated by a combined approach consisting of trapping reactions, isotopic labeling, kinetic studies, and computations on the DFT level.
- Rosenau, Thomas,Potthast, Antje,Kosma, Paul
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Read Online
- Aminomethylation of BINOL with methyleneiminium salts
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A new method for synthesizing chiral 3,3′-bis(N,N-dialkylaminomethyl) -1,1′-bi-2-naphthols with high enantiomeric excess is described. The procedure consists of bis-lithiation of diprotected (S)-or (R)-1,1′-bis(2- naphthol) followed by treatment of the intermediate with methyleneiminium salts. Mild reaction conditions prevent racemization and provide 3,3′-bis(N,N- dialkylaminomethyl)-1,1′-bi-2-naphthols or 3-(N,N-dialkylaminomethyl)-1, 1′-bi-2-naphthols with an enantiomeric excess >99%.
- Shustov, Gennady,Khlebnikov, Vladimir
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experimental part
p. 1319 - 1324
(2011/12/13)
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- Substituted Sulfonamide Compounds
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Substituted sulfonamide compounds corresponding to the formula I wherein m, n, p, Q, R1, R2, R3, R4, X, Y and Z have the respective meanings defined herein, pharmaceutical compositions containing such compounds, a process for their preparation, and the use of such compounds for the treatment and/or inhibition of pain and other conditions mediated by bradykinin receptor 1 (B1R) and/or bradykinin receptor 2 (B2R).
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Page/Page column 36-37
(2009/07/25)
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- SUBSTITUTED SULFONAMIDE DERIVATIVES
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The invention relates to substituted sulfonamide derivatives of the general formula (I'); processes for their preparation, medicaments containing these compounds, and the use of substituted sulfonamide derivatives for the preparation of medicaments
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Page/Page column 110
(2009/08/16)
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- 4-oxo-4,7-dihydro-thieno[2,3-b]pyridine-5carboxamides as antiviral agents
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The invention provides a compound of formula I: wherein R1, R2, R3, and R4 have any of the values defined in the specification, or a pharmaceutically acceptable salt thereof, as well as processes and intermediat
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- Hypolipidemic effects of α, β, and γ-alkylaminophenone analogs in rodents
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A number of N-substituted β-alkylaminophenone derivatives including two (α- and two γ-alkylaminophenone analogs were synthesized and investigated for hypolipidemic activity in mice at 8 mg/kg/day ip. Most of these analogs were found to be significantly more active than lovastatin and clofibrate. N-Phenylpiperazinopropiophenone 16 was one of the best derivatives, lowering serum cholesterol levels 41% and serum triglyceride levels 48% after 16 days of drug administration in CF1 mice. In Sprague-Dawley rats, N-phenylpiperazinopropiophenone at 8 mg/kg/day orally also demonstrated more potent hypolipidemic activity than clofibrate, gemfibrozil, and lovastatin at their therapeutic dosage. It significantly reduced tissue cholesterol and triglyceride levels in the aorta wall tissue and lowered the cholesterol and triglyceride levels in chylomicron, very low density lipid (VLDL) and low density lipid (LDL) fractions, while it significantly elevated the cholesterol levels in high density lipid (HDL) fraction. This compound also proved to be active in lowering both cholesterol and triglyceride levels in hyperlipidemic mice and rats induced with atherogenic diet. In vitro liver acetyl coenzyme A (CoA) synthetase, 3-hydroxy-3-methyl glutaryl (HMG) CoA reductase, acyl CoA cholesterol acyl transferase (ACAT), sn-glycerol-3-phosphate acyltransferase, phosphatidylate phosphohydrolase, and hepatic lipoprotein lipase activities were significantly inhibited by N-phenylpiperazinopropiophenone from 25 to 100 μM.
- Huang,Hall
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p. 281 - 290
(2007/10/03)
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- MANNICH REACTIONS OF FURAN AND 2-METHYLFURAN USING PRE-FORMED IMONIUM SALTS
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Good yields of 2-dialkylaminomethylfurans are obtained when N,N-dialkylmethylene-imonium chlorides are allowed to interact with furan in acetonitrile at room temperature; similar results are obtained using 2-methylfuran.
- Heaney, Harry,Papageorgiou, George,Wilkins, Robert F.
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p. 2377 - 2380
(2007/10/02)
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- SYNTHESIS AND NMR STUDY OF MANNICH BASES OF 8-ACETOXY-INDOLIZINES
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Crystallized hydrochlorides of some unstable Mannich bases derived from 8-acetoxyindolizine (1) and 3-acetyl-8-acetoxyindolizine (3) have been prepared by condensation of iminium salts on these substrates.The nmr study of the free bases and their hydrochlorides shows the selectivity of the reaction which introduces the aminomethyl side chain at position 3 in 1 and 1 in 3.The disappearance of the strong deshielding observed for H-5, in the 3-acetyl series, when one passes from the free to the corresponding hydrochloride is discussed in term of restricted rotation and dipolar interactions.
- Sliwa, Henri,Blondeau, Dominique
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p. 2159 - 2167
(2007/10/02)
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- 3-(Substituted aminomethyl)-7-substituted-3,5-dihydro-as-triazino[4,3-a][1,5]benzodiazepines
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A compound of the formula: SPC1 Wherein R, R0, and R3 are hydrogen or alkyl of 1 to 3 carbon atoms, inclusive; wherein R1 and R2 are alkyl of 1 to 3 carbon atoms, or the group EQU1 together is pyrrolidino, piper
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