2827-46-5Relevant articles and documents
METHOD FOR ALKYLATING AN AMINO COMPOUND
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Page/Page column 13, (2018/06/12)
The invention relates to a method for alkylating an amino compound, characterized in that at least one triazine derivative of general formula (I) or at least one urea or urea derivative of the general formula (II), (II), wherein ? R4 and R5 mean independently from each other Q1 or a moiety of the formula R6-N-R7 or R8-N-R9 bound with its central nitrogen atom to the triazine ring of the structure of formula (I), whereat - Q1 means a linear or branched C1-C30-alkyl or a cyclic substituent in form of a C5-C20-cycloalkyl, a C5-C20-aryl, a C1-C20-alkylsubstituted C5-C20-aryl or an amide of a cyclic unsaturated carboxylic acid, whereat the C1-C30-alkyl or the cyclic substituent can be interrupted by one or multiple oxygen atoms, sulphur atoms, substituted nitrogen atoms and/or by one or multiple groups of the type –C(O)O-,-OC(O)-,-C(O)- and/or –OC(O)O-, ? R1, R2, R3, R6, R7, R8 and R9 mean independently from each other H, linear or branched C1-C20-alkyl, C5-C20-cyclo alkyl, C5-C20-aryl, C1-C20-alkylsubstituted C5-C20-aryl, which in each case can be interrupted by one or multiple oxygen atoms, sulphur atoms and/or substituted nitrogen atoms and/or by one or multiple groups of the type –C(O)O-, - OC(O)-, -C(O)- and/or –OC(O) O- and/or can be functionalized by one or multiple hydroxyl groups and/or mercapto groups, and ? X means O or S, is reacted with at least one alcohol of the general formula (III) R10-OH wherein R10 means a linear or branched C1-C20-alkyl, C5-C20-cycloalkyl, or C1-C20- alkylsubstituted C5-C20-aryl, which can be in each case interrupted by one or multiple oxygen atoms, sulphur atoms, substituted nitrogen atoms and/or by one or multiple groups of the type –C(O)O-, -OC(O)-, -C(O)- and/or –OC(O)O- and/or can be functionalized by one or multiple hydroxyl groups and/or mercapto groups, wherein the reaction is carried out in the presence of at least one Ruthenate of the general formula (IV) Mn(RuO4) and/or at least one Perruthenate of the general formula (V) M(RuO4)n wherein the cation M is selected from a group comprising an alkali, earth alkali or substituted or non-substituted ammonium cation.
N-Methylmelamines: Synthesis, Characterization, and Physical Properties
List, Manuela,Puchinger, Helmut,Gabriel, Herbert,Monkowius, Uwe,Schwarzinger, Clemens
, p. 4066 - 4075 (2016/06/09)
N-Methylmelamines have recently gained importance as valuable compounds for manufacturing modified melamine formaldehyde resins and other polymer building blocks. A great advantage of these polymers is the reduction of the carcinogenic formaldehyde. Selecting the polymerization processes (e.g., substance polymerization, polymerization in solution) and controlling the polymerization reaction and properties of these novel materials requires knowledge of the properties of the individual melamine derivatives used as new building blocks. All possible permutations of N-methylmelamines were prepared, and reaction progress was monitored by GC/MS. 2,4,6-Tris(dimethylamino)-1,3,5-triazine was prepared to complete the series; this is, however, also a possible byproduct in various synthesis routes. The reaction conditions were optimized to obtain high yields of each derivative with the highest possible purity. The substances were characterized by NMR and IR spectroscopy, mass spectrometry, elemental analysis, and single-crystal X-ray diffraction. In addition, physical properties, such as solubility, melting points, and pKb values, were determined. The number of amino-, methylamino-, and dimethylamino groups has a significant effect on these properties. In summary, we found that by increasing the number of amino- and methylamino groups, solubility and pKb increase. With increasing number of amino groups, the compounds tend to form hydrogen bonds, and thus, the melting point shifts to higher temperature ranges where they start to decompose.
Method for modifying a triazine compound
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Paragraph 0027; 0039, (2015/12/19)
The present invention relates to a method for modifying a triazine compound comprising the steps of a) Providing at least one triazine compound of the general formulae (I) wherein - R1 and R2 mean independently from each other Q1 or a moiety of the formula R3-N-R4 or R5-N-R6 bound with its central nitrogen atom to the triazine ring of the structure of formula (I), whereat - Q1 means H, hydroxyl, a linear or branched C1-C30-alkyl or a cyclic substituent in form of a C5-C20-cycloalkyl, a C5-C20-aryl, a C1-C20-alkylsubstituted C5-C20-aryl, wherein in each case one or multiple carbon atoms can be substituted by one or multiple oxygen atoms, sulphur atoms, substituted nitrogen atoms and/or by one or multiple groups of the type -C(O)O-,-OC(O)-,-C(O)- and/or -OC(O)O-, and/or can be functionalized by one or multiple hydroxyl groups and/or mercapto groups, - R3, R4, R5 and R6 mean independently from each other H, linear or branched C1-C20-alkyl, C5-C20-cyclo alkyl, C5-C20-aryl, C1-C20-alkylsubstituted C5-C20-aryl, wherein in each case one or multiple carbon atoms can be substituted by one or multiple oxygen atoms, sulphur atoms and/or substituted nitrogen atoms and/or by one or multiple groups of the type -C(O)O-, -OC(O)-, -C(O)- and/or -OC(O)O-, and/or can be functionalized by one or multiple hydroxyl groups and/or mercapto groups; or an amide of a carboxylic acid or an imide of a cyclic dicarboxylic acid, and b) Reacting said aminotriazine of the general formulae (I) with at least one ammonium salt of the general formulae (II) ???????? [(R7R8H2N+]nXn- wherein R7 and R8 linear or branched C1-C20-alkyl, C5-C20-cycloalkyl, or C1-C20-alkylsubstituted C5-C20-aryl or cyclic amines, or wherein R7 and R8 together form an alkyl ring, wherein in each case one or multiple carbon atoms can be substituted by one or multiple oxygen atoms, sulphur atoms and/or substituted nitrogen atoms and/or by one or multiple groups of the type -C(O)O-, -OC(O)-, -C(O)- and/or -OC(O) O- and/or can be functionalized by one or multiple hydroxyl groups and/or mercapto groups, and wherein R7 and R8 can be the same or different; wherein Xn- is an anion of an organic or inorganic acid, and wherein n ≥1, in particular 1, 2 or 3, and c) wherein the reaction takes place in a salt melt of the at least one ammonium salt of the general formuale (II).
Melamine based Mannich-compounds and a process for obtaining the same
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Page/Page column 16, (2011/06/26)
The present invention relates to Melamine based Mannich compounds of the general formulae (1)-(12) and a process for synthesizing melamine based Mannich-products products comprising the steps of a) reacting at least one substituted melamine with at least one aldehyde, in particular formaldehyde, under basic conditions to form at least one OH-containing compound, b) reacting the at least one OH-containing compound in the presence of a catalysts to form at least one mannich-base, c1) reacting the at least one mannich-base with at least one enol-forming carbonyl compound, or c2) reacting the at least one mannich-base with at least one aromatic compound, and d) working up the reaction mixture. The invention relates further to pre-condensates obtainable from these products.
Synthesis and cytotoxic activity of trisubstituted-1,3,5-triazines
Arya, Kapil,Dandia, Anshu
, p. 3298 - 3304 (2008/02/09)
1,3,5-Triazine derivatives were screened for phototoxicity as well as the cytotoxic activities against leukemia and adenocarcinoma derived cell lines in comparison to the normal human keratinocytes. A simple and environmentally friendly procedure has been developed for the synthesis of 1,3,5-triazine derivatives under microwave irradiation in the presence of a HY zeolite. The catalyst can be recovered and reused. Thus, the procedure provides a simple and green synthetic methodology under environmentally friendly conditions. Structure-activity relationships between the chemical structures and antimycobacterial and photosynthesis-inhibiting activity of the evaluated compounds are also discussed.
PROCESS FOR PREPARING N-METHYLATED MELAMINES
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Page 4, (2008/06/13)
The present invention provides a process for preparing N-methylated melamines in simple steps by using inexpensive raw materials in such a manner that the proportion of mono-type, bis-type and tris-type of the N-methylated melamines as prepared can be controlled. The process comprises reacting by heating melamine with methylamine in the presence of an acidic catalyst under pressure to substitute at least one amino group of the melamine by methylamino group
Framework-reactive siderophore analogs as potential cell-selective drugs. Design and syntheses of trimelamol-based iron chelators
Ramurthy, Savithri,Miller, Marvin J.
, p. 4120 - 4124 (2007/10/03)
Currently, the role of DNA-directed alkylating agents as potential anticancer/antimicrobial drugs is of wide interest. Most of the alkylating agents used clinically as drugs damage DNA in cells without specificity, and this can lead to undesired toxicity problems. Minimizing serum residence time by targeting the drug to select pathogens or organs might diminish the effects of nonselective reactivity. This paper describes the syntheses and preliminary studies of analogs of siderophores (microbial iron chelators) 2 and 20 that incorporate centers within the siderophore framework capable of generating potent electrophiles (iminium ions), hopefully after directed cellular recognition and uptake. Formation of N-aminals from trimelamol (3) and substituted hydroxamic acid 4 or 5 was critical for the design and synthesis of the targets. In preliminary biological testing, compound 2, a trimelamol-based siderophore analog, was active against Escherichia coli X580, illustrating the therapeutic potential of this new type of siderophore-mediated drug design and delivery.
Studies on the stability of trimelamol, a carbinolamine-containing antitumor drug
Jackson,Crabb,Gibson,Godfrey,Saunders,Thurston
, p. 245 - 251 (2007/10/02)
The stability of trimelamol (N2,N4,N6-trimethylol-N2,N4,N6-trimethylmelamine) a synthetic carbinolamine-containing antitumor drug, has been studied. Two major degradation pathways have been characterized and a unified mechanism proposed to rationalize the chemistry involved. One degradation pathway involves the consecutive loss of hydroxymethylene units by elimination of formaldehyde until the parent trimethylmelamine (4) results. An HPLC method was used to obtain kinetic data for the loss of trimelamol and to monitor the order of appearance of three degradation products. This pathway was shown to follow first-order kinetics at all pH values studied at both 18 and 37°C. The second pathway involves the coupling of two trimelamol molecules via a methylene bridge to form bis(trimelamol) (6) which had been previously refered to in the literature as a ''polymer''. This reaction is acid catalyzed and temperature dependent. Bis(trimelamol) is virtually water insoluble and adheres strongly to glass surfaces. Finally, t( 1/2 ) values have been determined for trimelamol in aqueous solution at different temperatures, and the kinetics of formation of degradation products has been studied over a period of 30 h under a variety of conditions of pH and temperature. The data reported here are relevant to both the formulation and clinical administration of trimelamol, and may contribute to an understanding of mechanism of action and future analogue development studies.
