Showing papers on "Morpholine published in 2005"
TL;DR: Results strongly suggest that the ruthenium-catalyzed anti-Markovnikov addition of alkylamines to vinylarenes occurs by a new reaction mechanism for hydroamination involving nucleophilic attack on the eta6-vinylarene complex and exchange of the aminoalkylarenes complex product with free vinylarene.
Abstract: Studies are described that reveal the steps of the anti-Markovnikov hydroamination of vinylarenes with alkylamines catalyzed by Ru(COD)(2-methylallyl)2, bis(diphenylphosphino)pentane, and TfOH. Treatment of the catalyst components with an excess of styrene under the catalytic reaction conditions afforded a new ruthenium η6-styrene complex with an ancillary tridentate PCP ligand. This ruthenium complex was active as catalyst for the hydroamination of styrene with morpholine to give the anti-Markovnikov adduct as a single regioisomer in high yield. Studies of the reactivity of the η6-styrene complex revealed two reactions that comprise a catalytic cycle for anti-Markovnikov hydroamination: nucleophilic addition of morpholine to the ruthenium η6-styrene complex to afford a ruthenium η6-(2-aminoethyl)benzene complex and arene exchange of the ruthenium η6-(2-aminoethyl)benzene complex with styrene to regenerate the ruthenium η6-styrene complex. The addition of morpholine and the exchange of arene occurred wit...
115 citations
TL;DR: In this article, the rhodium catalyzed hydroaminomethylation of 1-octene with morpholine has been studied using temperature-dependent solvent systems (TMS systems).
Abstract: The rhodium catalyzed hydroaminomethylation of 1-octene with morpholine has been studied using temperature-dependent solvent systems (TMS systems). High conversions of the olefin and high selectivities to the amines are obtained in TMS systems consisting of propylene carbonate, an alkane and a semi-polar mediator, although some morpholine reacts with propylene carbonate in a side reaction. With N-octylpyrrolidone as mediator the conversion of 1-octene and the selectivity of the corresponding amines reached in each time 92%. After the reaction the catalyst can be easily recovered by a simple phase separation with only a negligible loss of the rhodium catalyst.
73 citations
TL;DR: 4-methyl-and 4-phenyl-substituted derivatives, which were the most active compounds within this series, inhibited caspase-3 with IC50 of 23 and 27 nM, respectively.
Abstract: Synthesis, biological evaluation, and SAR dependencies for a series of novel 1,3-dioxo-2,3-dihydro-1H-pyrrolo[3,4-c]quinoline inhibitors of caspase-3 are described. The inhibitory activity of the synthesized compounds is highly dependent on the nature of 4-substituents on the core scaffold. 4-methyl-and 4-phenyl-substituted derivatives, which were the most active compounds within this series, inhibited caspase-3 with IC50 of 23 and 27 nM, respectively.
69 citations
TL;DR: In this paper, the inhibiting properties of four macrocyclic cobalt(III) complexes of the general formula [CoIII(Rdtc)cyclam](ClO4)2, where cyclam and Rdtc− refer to 1,4,8,11-tetraazacyclotetradecane and morpholine-, thiomorpholine-, piperazine-, N-methylpiperazine-dithiocarbamates, respectively, have been studied on the corrosion of iron in aerated 0.1 ǫ M H
68 citations
TL;DR: (S,S)-Reboxetine was synthesized stereospecifically in 30% overall yield and 99% ee in eight steps using selective oxidation of an N-protected hydroxymethylmorpholine and aryl-chromium-mediated aromatic nucleophilic substitution.
66 citations
TL;DR: By combining a Staudinger/aza-Wittig and an Ugi three-component reaction in a one-pot process (SAWU-3CR), a new and efficient multicomponent reaction was developed and gave easy access to highly functionalized, enantiomerically pure pipecolic acid amides and bridged morpholine amide derivatives.
Abstract: By combining a Staudinger/aza-Wittig and an Ugi three-component reaction in a one-pot process (SAWU-3CR), a new and efficient multicomponent reaction was developed. The application of this reaction on readily available azido-aldehydes gave easy access to highly functionalized, enantiomerically pure pipecolic acid amides and bridged morpholine amide derivatives. The versatility of this methodology is demonstrated by the construction of a molecular library.
61 citations
Patent•
09 Mar 2005
TL;DR: In this paper, the authors proposed a method for the removal of carbon dioxide from a gas flow with a carbon dioxide partial pressure in the gas flow of less than 200 mbar, whereby gas flow is brought into contact with a liquid absorption agent, selected from an aqueous solution of an amino compound with at least two tertiary amino groups in the molecule.
Abstract: The invention relates to a method for the removal of carbon dioxide from a gas flow with a carbon dioxide partial pressure in the gas flow of less than 200 mbar, whereby the gas flow is brought into contact with a liquid absorption agent, selected from an aqueous solution (A) of an amino compound with at least two tertiary amino groups in the molecule and (B) an activator, selected from the primary and secondary amines, or (A) a tertiary aliphatic amine, the reaction enthalpy ΔRH for the protonation of which is greater than that for methyldiethanolamine and (B) an activator, selected from 3-methylaminopropylamine, piperazine, 2-methylpiperazine, N-methylpiperazine, homopiperazine, piperidine and morpholine. The method is particularly suitable for the treatment of flue gases and also relates to an absorption agent.
60 citations
TL;DR: The crystal structures of the proton transfer compounds of 5-nitrosalicylic acid (5-nsa) with morpholine (morph), hexamethylenetetramine (hmt), and ethylenediamine (en) have been determined and their solid-state packing structures described.
Abstract: The crystal structures of the proton-transfer compounds of 5-nitrosalicylic acid (5-nsa) with morpholine (morph), hexamethylenetetramine (hmt), and ethylenediamine (en) have been determined and their solid-state packing structures described. The compounds are [(morph)+(5-nsa)–] 1, [(hmt)+(5-nsa)–·H2O] 2, and [(en)2+2(5-nsa)–·H2O] 3. In all compounds, protonation of the hetero-nitrogen of the Lewis base occurs. With 1, the 5-nsa anions and the morpholine cations lie, respectively, in or across crystallographic mirror planes and are linked within the planes by hydrogen-bonding interactions through the aminium group and the carboxylic and phenolic oxygens of the anionic 5-nsa species giving a two-dimensional sheet polymer. Compound 2 is an unusual structure with the planar 5-nsa anions lying within pseudo mirror planes and cyclically linked by duplex water bridges through a single carboxylate oxygen into centrosymmetric dimers. The hmt cation molecules are disordered across the pseudo mirror and are strongly linked by N+–H···O hydrogen bonds only to the water molecules with peripheral weak hmt C–H···O hydrogen bonds extending the dimer within and between the dimer planes. Compound 3 is a network polymer comprised of the 5-nsa anions, the en dianions, and the water molecule in an extensive hydrogen-bonded structure.
57 citations
TL;DR: In this article, it was shown that HMPA and amine used as solvents facilitate transmetallation of the ethynyl group on 1 to the palladium by intermolecular coordination between antimony and oxygen (for HMPA) or nitrogen (for amine).
55 citations
TL;DR: The most active compound within this series, 7{49} and 7{58}, inhibited caspase-3 with IC50=3 nM, and represents a new chemotype of nonpeptide small molecule inhibitors of caspases-3.
51 citations
TL;DR: The synthesis and antibacterial activity of oxazolidinones containing dihydro-1,2-oxazine and 2-pyrazoline ring systems are described and both had potency similar to linezolid against a panel of Gram-positive bacteria.
TL;DR: Under microwave irradiation and solvent-free conditions, cyanoacetates (cyanoacetamides) react with ketones and sulphur in the presence of a small amount of morpholine to give 2-amino-thiophene-3-carboxylic derivatives.
TL;DR: Good fungicidal results were obtained against the various types of fungi under investigation and the target compounds showed good inhibition towards Gram +ve bacteria, Gram -ve bacteria and yeast.
TL;DR: An efficient new method is reported for the chemical synthesis ofcyl glucuronides by selective 1beta-acylation of allyl glucuronate with carboxylic acids catalyzed by HATU and then mild deprotection through treatment with Pd(PPh(3))(4) and morpholine.
TL;DR: The structures of newly synthesized compounds were evidenced from their spectral and micro-analytical data as mentioned in this paper, which showed that all newly synthesised compounds were shown to have similar structures.
Abstract: 6-Aryl-4-pyrazol-1-yl-pyridazin-3-one (1) reacted with a PCl5POCl3 mixture to give the 3-chloropyridazine derivative 3. Reaction of 3 with 2-hydroxybenzoylhydrazide and semicarbazide hydrochloride afforded 4 and 5. Reaction of 1 with ethyl chloroacetate gave 8. Reaction of 8 with hydrazine hydrate yielded the hydrazide 9. The hydrazide 9 condensed with the acetylenic ketones and esters 10a10d and acetylacetone to give the adducts 11a, 11b, 12, 13, and 14. Reacting 1 with formaldehyde and piperidine, morpholine, or piperazine, 3-bromopropanoic acid, acetic anhydride, p-toluenesulphonyl chloride, succinyl chloride, oxalyl chloride, ethanolamine, or ethyl chloroacetate gave the adducts 1522. The structures of all newly synthesized compounds were evidenced from their spectral and microanalytical data. Key words: 6-aryl-4-pyrazol-1-yl-pyridazinone derivative, 6-aryl-3-chloropyridazine derivative, 3,6-diaryl-1,2,4-triazino[4,3-b]pyridazine derivative, 6-aryl-3-ethoxycarbonylmethoxypyridazine derivative, 6-ar...
Patent•
25 Feb 2005TL;DR: In this article, a scavenger was selected from a 1,3,5-trisalkanylamino hexahydro-1, 3, 5-triazine derivative or morpholine or piperazine derivative.
Abstract: Hydrogen sulfide and mercaptans may be removed from a fluid or gaseous stream by reacting the hydrogen sulfide and mercaptans in the stream with a scavenger selected from a: (i.) 1,3,5-trisalkanylamino hexahydro-1,3,5-triazine derivative; (ii.) morpholine or piperazine derivative; (iii.) amine oxide; (iv.) alkanolamine; or (v.) aliphatic or aromatic polyamine.
TL;DR: Aryllithium generated by lithium-iodine exchange undergo intramolecular cyclisation to give pyrrolo[1,2-b ]isoquinolines, in high yields.
TL;DR: In this paper, the development of an asymmetric route to an aminomethyl morpholine intermediate via palladium-catalysed allylic substitution is described, which is a variant of the asymmetric path described in this paper.
TL;DR: Amphiphilic maleic anhydride-stearyl methacrylate (MA-SMA) random copolymers were synthesized via the free radical copolymerization and its amide was prepared through the MA moieties being reacted with morpholine as mentioned in this paper.
TL;DR: In this article, the reaction of imidazole, pyrazole, pyrrole, morpholine, and piperazine with dimethyl carbonate to afford N−methylated products was reported.
TL;DR: The results indicate that the amidine derivatives of anthracyclines show similar, but not identical sequence specificity as parent compounds, though they exert their effect at a higher concentration.
TL;DR: In this paper, a simple system that monitors NO2 gas in air was developed, which was used for one-shot detection of NO2 concentrations in air using poly(styrene-co-chloromethyl styrene) reaction with morpholine.
Abstract: Piezoelectric devices coated with cross-linked poly(styrene-co-chloromethyl styrene) reacted with morpholine were fabricated to develop a simple system that monitors NO2 gas in air. The introduction of NO2 gas irreversibly decreased the oscillation frequencies of all the devices tested, indicating that these devices can be used for one-shot detection of NO2 concentrations in air. The NO2 sensitivity was defined as hourly changes in frequency. The use of the cross-linked structure clearly increased sensitivity. The largest sensitivity obtained in this study was 1200 Hz/h for 50 ppm of NO2, which demonstrated a sub-ppm level of NO2 detection.
TL;DR: In this article, the cycloaddition of organic azides with some conjugated enamines of the 2-amino-1,3-diene, 1-amide, and 2-aminobut-1-en-3-yne type is investigated.
Abstract: The cycloaddition of organic azides with some conjugated enamines of the 2-amino-1,3-diene, 1-amino-1,3-diene, and 2-aminobut-1-en-3-yne type is investigated. The 2-morpholinobuta-1,3-diene 1 undergoes regioselective [3+2] cycloaddition with several electrophilic azides RN32 (a, R=4-nitrophenyl; b, R=ethoxycarbonyl; c, R=tosyl; d, R=phenyl) to form 5-alkenyl-4,5-dihydro-5-morpholino-1H-1,2,3-triazoles 3 which are transformed into 1,5-disubstituted 1H-triazoles 4a,d or α,β-unsaturated carboximidamide 5 (Scheme 1). The cycloaddition reaction of 4-[(1E,3Z)-3-morpholino-4-phenylbuta-1,3-dienyl]morpholine (7) with azide 2a occurs at the less-substituted enamine function and yields the 4-(1-morpholino-2-phenylethenyl)-1H-1,2,3-triazole 8 (Scheme 2). The 1,3-dipolar cycloaddition reaction of azides 2a–d with 4-(1-methylene-3-phenylprop-2-ynyl)morpholine (9) is accelerated at high pressure (ca. 7–10 kbar) and gives 1,5-disubstituted dihydro-1H-triazoles 10a,b and 1-phenyl-5-(phenylethynyl)-1H-1,2,3-triazole (11d) in significantly improved yields (Schemes 3 and 4). The formation of 11d is also facilitated in the presence of an equimolar quantity of tBuOH. The three-component reaction between enamine 9, phenyl azide, and phenol affords the 5-(2-phenoxy-2-phenylethenyl)-1H-1,2,3-triazole 14d.
Patent•
25 Apr 2005
TL;DR: In this paper, the authors provided quinazoline compounds of the formula: wherein R 1 is halo, R 2 is H or halo; R 3 is a) C 1-C3 alkyl, optionally substituted by halo and R 4 is -(CH2)m-Het; m is 1-3; and X is O, S or NH; or a pharmaceutically acceptable salt thereof.
Abstract: The invention provides quinazoline compounds of the formula: wherein R1 is halo; R2 is H or halo; R3 is a) C1-C3 alkyl, optionally substituted by halo; or b) -(CH2)n-morpholino, -(CH2)n-piperidine, -(CH2)n-piperazine, -(CH2)n-piperazine-N(C1-C3 alkyl), -(CH2)n-pyrrolidine, or -(CH2)n imidazole; n is 1 to 4; R4 is -(CH2)m-Het; Het is morpholine,piperidine, piperazine, piperazine-N(C1-C3 alkyl), imidazole,pyrrolidine, azepane, 3,4-dihydro-2H-pyridine, or 3,6-dihydro-2H-pyridine, each optionally substituted by alkyl, halo, OH, NH2, NH(C1-C3 alkyl) or N (C1-C3 alkyl)2; m is 1-3; and X is O, S or NH; or a pharmaceutically acceptable salt thereof, as well as processes and intermediate compounds for making them, useful pharmaceutical compositions and methods of using the compounds in the treatment of proliferative diseases.
TL;DR: Amines (piperidine, morpholine, diisopropylamine, terbutylamine), which may be used as bases in copper-free palladium-catalyzed Sonogashira reactions, substitute one phosphane PPh3 in trans-ArPdX(PPh3)2 complexes as discussed by the authors.
Abstract: Amines (piperidine, morpholine, diisopropylamine, terbutylamine), which may be used as bases in copper-free palladium-catalyzed Sonogashira reactions, substitute one phosphane PPh3 in trans-ArPdX(PPh3)2 complexes (Ar = Ph, 4-NC–C6H4, 4-MeOC–C6H4, 2-thienyl; X = I, Br, Cl) to generate ArPdX(PPh3)(amine) complexes in a reversible reaction whose equilibrium constant is determined in chloroform, THF, and DMF. The equilibrium constant depends on Ar, X, the basicity, and the steric hindrance of the amine. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2005)
TL;DR: In spite of partial deprotonation upon inclusion of morpholine, Dianin's compound maintains its well-known clathrate structure in the solid state.
Patent•
09 Mar 2005TL;DR: In this paper, the present invention relates to morpholine and thiomorpholine derivatives of the general formula I or pharmaceutically acceptable salts thereof and their use and is related to the present paper.
Abstract: The present invention relates to morpholine and thiomorpholine derivatives of the general formula I or pharmaceutically acceptable salts thereof and their use.
TL;DR: In this paper, the linkage isomers trans-bis[4-(2-aminoethyl)morpholine]dinitronickel(II) (brown, 1a) andtrans-bis [4-( 2-amide)-morpholine)dinitritonickel (II)(blue-violet, 1b) have been synthesized from solution.
Patent•
19 Apr 2005TL;DR: In this paper, the authors defined R'- Re, A, X, and Z as compounds of the formulae (I, (II), (III), (IV), (V), (VI) and (VIII) for the treatment of central nervous system disorders.
Abstract: This invention relates to compounds of the formulae (I), (II), (III), wherein R'- Re, A, X, and Z are defined as in the specification, pharmaceutical compositions containing them and their use in the treatment of central nervous system disorders.
TL;DR: The asymmetric oxidation of sulfides to sulfoxides was realized with layered double hydroxides (LDH)-supported OsO4 catalyst using N-methyl morpholine Noxide as co-oxidant and (DHQD)2PHAL (hydroquinidine 1,4-phthalazinediyl diether) as a chiral ligand in good yields albeit moderate enantiomeric excess.
Abstract: The asymmetric oxidation of sulfides to sulfoxides is realised with layered double hydroxides (LDH)-supported OsO4 catalyst using N-methyl morpholine N-oxide as co-oxidant and (DHQD)2PHAL (hydroquinidine 1,4-phthalazinediyl diether) as a chiral ligand in good yields albeit moderate enantiomeric excess (e.e's).