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Morpholine

About: Morpholine is a research topic. Over the lifetime, 5411 publications have been published within this topic receiving 51063 citations. The topic is also known as: diethylene imidoxide & diethylene oximide.


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Patent
07 Sep 1960
TL;DR: In this paper, the authors described a set of dyes of the formula where the ring A may contain a sulphonic acid group or up to two halogen atoms, the ring B may be substituted by halogen, alkoxy, alkyl, sulphonic acids or carboxylic acid, n and m are each 0 or 1, Y is -SO2-,-CO- or -NR2CO- where R2 is hydrogen or alkyls the carbonyl being attached to the alkylene radical, R and R1 are each hydrogen,
Abstract: The invention comprises dyes of the formula where the ring A may contain a sulphonic acid group or up to two halogen atoms, the ring B may be substituted by halogen, alkoxy, alkyl, sulphonic acid or carboxylic acid, n and m are each 0 or 1, Y is -SO2-,-CO- or -NR2CO-where R2 is hydrogen or alkyl the carbonyl being attached to the alkylene radical, R and R1 are each hydrogen, alkyl, hydroxyalkyl, sulphatoalkyl, sulphoalkyl, cycloalkyl, aralkyl, sulphonated aralkyl, aryl or substituted aryl, X is a divalent aliphatic radical or for an aromatic radical if neither R nor R1 is aromatic, and Z is an aryl radical which contain a group capable of reaction with cellulose fibre to form a covalent bond. Specified acyl radicals are those of acrylic, a -chloracrylic, propiolic, maleic, mono- and dichloromaleic, chloroacetic, sulphochloroacetic, b -chloro- and b -bromopropionic and a :b -dichloropropionic acids and radicals derived by reaction of one of the halogen atoms of 2:4:6-tribromo- and trichloro-pyrimidine, 2:4:5:6-tetrachloropyrimidine 5-methyl-, 5-nitro- and 5-cyano-2:4:6-trichloropyrimidine, 5-carboxy-, 5-carboethoxy-, 5-nitro-6-methyl- and 5-nitro-2:4-dichloropyrimidine, cyanuric bromide, cyanuric chloride and primary condensation products of cyanuric chloride or bromide with ammonia, methanol, ethanol, isopropanol, phenol, o-, m- and p-chlorophenol, o-, m- and p-cresol, o-, m- and p-sulphophenol, thiophenol, thioglycollic acid, diethyldithiocarbamic acid, mercaptobenzthiazole, methyl-, dimethyl-, ethyl-, diethyl-, n-propyl-, isopropyl-, butyl-, hexyl- and cyclohexyl-amine, toluidine, piperidine, morpholine, methoxyethylamine, ethanolamine, aminoacetic acid, aniline-2:5-disulphonic acid, orthanilic, metanilic and sulphanilic acid, 2-, 3- and 4-aminobenzoic acid, 5-amino-2-hydroxybenzoic acid, 2-aminoethane-sulphonic acid, aminonaphthalene mono- and di-sulphonic acid and N-methylaminoethane sulphonic acid. The dyes are made by acylating compounds of the above formula where Z is hydrogen and A, B, X, Y, R, R1, m and n are as above with an anhydride or acid halide of an acid containing a group capable of reacting with cellulose fibres. The compounds where Z is hydrogen are made by reacting compounds of the formulae or where A, B, Y and n are as above, Q is halogen, an esterified hydroxyl group or -S-Z where Z is a heterocycle or a negatively substituted phenyl group and Q1 is an alkenyl group having the unsaturated link in a :b -position to Y, with a compound of the formula and if desired sulphating or sulphonating the products, or by condensing a compound of the formula where P is chlorine or bromine, with an amine of the formula Examples are given. The dyes dye and print cotton, viscose rayon, regenerated cellulose, wool, silk, cellulose acetate, polyamides, polyacrylonitrile and aromatic polyester fibres and dye and print cellulose fibres in conjunction with an acid-binding agent. Specifications 822,047, 848,742, 867,571, 885,059, 885,547, 885,814, 885,815, 887,723, 891,601 and 917,780 are referred to.

17 citations

Journal ArticleDOI
TL;DR: In this article, the synthesis of 2-(trifluoromethyl)acrylic acid (TFMAA) was carried out in the presence of PdCl 2 (PPh 3 ) 2.
Abstract: Esters and amides of 2-(trifluoromethyl)acrylic acid (TFMAA) have been synthesised by two different routes involving CO-chemistry. The alkoxycarbonylation of 2-bromo-3,3,3-trifluoropropene was carried out in the presence of PdCl 2 (PPh 3 ) 2 . High substrate conversions were obtained, but the yield in acrylic esters was generally low because the desired unsaturated esters reacted further adding a molecule of alcohol to the C–C double bond. The carbonylation of 2-bromo-3,3,3-trifluoropropene in the presence of secondary amines produced the corresponding unsaturated amides in high yields; the addition of the amine to the C–C double bond also occurred, but this side reaction was minimised by using secondary cyclic amines such as morpholine or piperidine. Alternatively, the acrylic esters can be obtained by hydromethoxycarbonylation of 3,3,3-trifluoropropyne using the catalytic system Pd(OCOCH 3 ) 2 /2-pyridyldiphenylphosphine/CH 3 SO 3 H. In this process the most important side product is the isomeric crotonic ester. The regioselectivity of the reaction can be controlled to a great extent by a suitable choice of the solvent.

17 citations

Journal ArticleDOI
TL;DR: In this article, the synthesis and structural studies of an [O,N,O, N′]-type phenolic ligand (H2L) and two new uranyl complexes of this ligand are described.

17 citations

Journal ArticleDOI
TL;DR: In this article, a morpholine ring system from epoxide and amino alcohol was constructed in a two-step process using a previous four-step synthesis, which was converted into a more efficient two-stage process.

17 citations

Journal ArticleDOI
TL;DR: The whole biological activity results revealed that the sulfonamide derivatives behaved as potent antifungal agents as compared to the carbamate derivatives.
Abstract: The precursor compound 3-fluoro-4-morpholinoaniline (7) is an important intermediate of the antibiotic drug linezolid and was synthesized initially by the substitution of morpholine (5) on 1,2-difluoro-4-nitrobenzene (4) under neat conditions, resulting in 4-(2-fluoro-4-nitrophenyl)morpholine (6) followed by its nitro group reduction with Fe/NH4Cl. A series of new sulfonamides (9a–e) and carbamates (11a–e) have been synthesized in good yields (75–89%) by the reaction of substituted aryl sulfonyl chlorides (8a–e) and substituted aryl/acyclic chloroformates (10a–e) with precursor compound 7, respectively, for biological interest. Structures of the title products were elucidated by spectroscopic data such as IR, NMR (1H and 13C NMR) and mass and elemental analyses. The antimicrobial potency of title products was examined by the screening of growth of zone of inhibition against four bacteria and four fungi, and minimum inhibitory concentration (MIC) was also determined. Most of the compounds showed good to potent antimicrobial activity, whereas the title products, 9d and 9e against bacterial strains, and 9a, 9b, 9d and 11a against fungi, exhibited promising activity in the MIC range of 6.25–25.0 µg/mL. The whole biological activity results revealed that the sulfonamide derivatives behaved as potent antifungal agents as compared to the carbamate derivatives. Molecular docking studies of the crystal structure of topoisomerase II gyrase A complexed with natural inhibitor, clorobiocin (1kzn), using the molecular operating environment (MOE) programme were performed in order to predict the affinity and orientation of the synthesized compounds at the active enzyme site. The test compounds showed good binding affinities and formed hydrogen bonds with a surrounding of amino acids at the active sight, whereas compounds 9d (−189.0 kcal/mol) and 11a (−280.3 kcal/mol) exhibited high binding affinities and good agreement with in vitro antimicrobial screening.

17 citations


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Performance
Metrics
No. of papers in the topic in previous years
YearPapers
202385
2022177
202191
2020135
2019129
2018143