Synthesis of Chiral 2,4-Chiral 2,4-Dichloro-6-menthoxy-1,3,5-triazines and 2-Chloro-4, 6-Dimenthoxy-1,3,5-triazines as Enantiodifferentiating Coupling Reagents. An X-ray Study on 2,4,6-Trimenthoxy-1,3,5-triazine

Chiral mono-di-and trimenthoxy-1,3,5-triazines ware obtained from natural menthol and cyanuric chloride and applied as enantioselective coupling reagents in the synthesis of dipeptides.     

The Oxidation of Hexahydrotriazines

Summary. N-Alkyl-2,4-dioxohexahydro-1,3,5-triazines oxidize readily with oxygen to the corresponding cyanuric acid derivates. The oxidation of 1,3,5-trimethyl-2,4-dioxohexahydro-1,3,5-triazine resulted in a stable form of hydroperoxide. During the oxidation of 1,3,5-trimethyl- 6-phenyl-2,4-dioxohexahydro-1,3,5-triazine this hydroperoxide could not be identified, however, the result was the stable reaction product bis-[6-phenyl-1,3,5-trimethyl-2,4-dioxohexahydro-1,3,5-triazin]peroxide.     

Microwave Assisted Synthesis of 2,4,6-Triarylamino-1,3,5-triazines as Potential UV Absorbent

Abstract

2,4,6-Triarylamino-1,3,5-triazines was synthesized in a few minutes by reaction of cyanuric chloride with aromatic amines under microwave irradiation. This method is featured with rapid reaction, convenient operation, high yield, and clean. UV-absorption was tested for each compound.     

Synthesis of 2,4,6-tri-substituted-1,3,5-triazines

Several specific synthetic protocols were developed for the preparation from cyanuric chloride of a range of symmetric and non-symmetric di- and tri-substituted 1,3,5-triazines containing alkyl, aromatic, hindered, chiral and achiral hydroxyalkyl, ester and imidazole groups via sequential nucleophilic substitution of the C-Cl bond by C-O, C-N and C-S bonds.     

Liquid crystalline 1,3,5-triazines incorporating rod-like azobenzene sub-units

New liquid crystalline 1,3,5-triazines are presented that incorporate three mesogenic groups based on rod-like azobenzene moieties. The synthesis was carried out by reaction of cyanuric chloride with 4-alkoxy-4-aminoazobenzene derivatives. The mesomorphic behaviour was investigated by polarizing microscopy, differential scanning calorimetry and X-ray scattering. Besides a nematic and a SmA phase, the trisazomelamines form a higher ordered mesophase within a broad temperature range below the smectic A phase. With respect to the rod-like azobenzene sub-units, the low temperature phases display a smectic 'bilayer' structure. The molecules are antiparallel aligned within one layer. Furthermore, 1,3,5-triazines incorporating just two azobenzene groups are presented, these were prepared to investigate the influence of the number of rod-like sub-units linked to the triazine core on the mesomorphic properties.     

The umpolung of substituent effect in nucleophilic aromatic substitution. A new approach to the synthesis of N,N-disubstituted melamines (triazine triskelions) under mild reaction conditions

By the umpolung of substituent effect 1,3,5-triazines substituted with three dialkylamino groups were prepared under mild reaction conditions by treatment of cyanuric chloride with tertiary amines. Quaternary N-triazinylammonium salts were identified as reactive intermediates activating the triazine ring and strongly promoting the persubstitution of all chlorine atoms. The final degradation of intermediate N-triazinylammonium chlorides proceeded at room temperature or in boiling dichloromethane spontaneously within irreversible evolution of appropriate chloroalkane.     

New disc-shaped triarylamino-1,3,5-triazines with heteroaromatic central cores

New disc-shaped triarylamino-1,3,5-triazines were prepared by reaction of cyanuric chloride with two-fold alkoxy substituted anilines. Each of the triarylmelamines exhibits an enanti-otropic mesophase. X-ray investigations reveal the formation of columnar liquid crystalline structures with either a hexagonal or a rectangular lattice. The lattice parameters, as well as the intracolumnar ordering, depend on the length of the flexible lateral side chains. The new melamines form Langmuir monolayers at the air/water interface due to their amphiphilic nature. The monolayer organization is characterized by a side-on arrangement of the molecules. The polar central molecular parts lie flat on the water, whereas the lateral alkyl chains are oriented perpendicular to the water surface.     

A convenient one-pot synthesis of trisubstituted 1,3,5-triazines through intermediary amidinothioureas

A thiophile-promoted one-pot synthesis of trisubstituted 1,3,5-triazines starting from isothiocyanates, N,N-diethylamidines, and carbamidines has been studied. The reaction proceeds through the formation of intermediary amidinothioureas, which react with carbamidines in the presence of mercury(II) chloride to generate the desired 1,3,5-triazines in good to moderate yields (40-70%).     

Mass spectra of chloro-, aminochloro- and ethylaminochloro-s-triazines

The mass spectra of cyanuric chloride and all of the possible amino-and ethylaminochloro-s-triazines have been investigated. The simpler compounds provide evidence for the structures of low mass fragment ions found in the spectra of the more complex derivatives. Fragmentation patterns are presented which account for most of the major ions. These pathways involve either the initial loss of a chlorine atom (important for the simple aminochlorotriazines) or ring cleavage with expulsion of cyanogen chloride (important for cyanuric chloride). The ethyl derivatives undergo cleavage of the side chain prior to either ring cleavage or chlorine expulsion.     

The synthesis and characterization of some 2,1,6-triaryl and alkylsulfonylhydrazido-s-triazines

2,4,6-Trialkyl- and triarylsulfonylhydrazido-s-triazines (I) have been synthesized by the reaction of cyanuric chloride with a variety of sulfonylhydrazides in a hydrocarbon solvent. The subject compounds (I) were characterized by elemental analysis, molecular weight and spectroscopy.     

Temperature dependence of the nitrogen-14 nuclear quadrupole resonance frequencies in selected triazine compounds

Symmetric-1,3,5 triazine compounds are heterocyclic ring molecules containing three nitrogen atoms at the 1,3,5 sites. Because of their inherent high symmetry and the existence of a large number of compounds with different chemical groups attached to the ring, this class of compounds is ideally suited to NQR studies. We are reporting measurements of T^★₂ and the temperature dependence of the frequencies for a number of the nitrogen-14 NQR lines in trichloromelamine, cyanuric acid, trichloroisocyanuric acid, cyanuric chloride, and melamine. The results of these measurements yielded T^★₂'s for cyanuric chloride almost an order of magnitude larger than for the other compounds. The variations of the frequencies with temperature appear to be consistent with the Bayer—Kushida model.     

2,4,6-三对氨基苯氧基-1,3,5-均三嗪的合成

以三聚氯氰和对硝基苯酚为原料,经取代、还原合成了2,4,6-三对氨基苯氧基-1,3,5-均三嗪。对Pd/C水合肼、SnCl2·2H2O-HCl及Pd/C催化加氢三种不同还原体系进行比较。采用1H-NMR、FT-IR和元素分析方法对产物进行结构表征。     

Derivatives Of ditraizinylamine and tritriazinylamine

2-Arylamino-4,6-dichloro-s-triazine reacts with cyanuric chloride in the presence of alkali to yield N,N-bis(4,6-dichloro-s-triazin-2-yl)-arylamine. In like manner, 2-substituted o-chloro-, p-chloro-, o-nitro- and p-carbomethoxyphenylamino-4,6-dimethoxy-s-triazines react with cyanuric chloride to yield the corresponding 4,6-dichloro-s-triazin-2-yl-4′,6′-dimethoxy-s-triazin-2′-ylaryl-amine, while anilino-, p-toluidino, o- and p-methoxyphenylamino and o-carbomethoxyphenylamino derivatives did not. The reaction of cyanuric chloride with 2,4-dichloro-6-ethylamino-s-triazine in the presence of alkali yields the condensation product of the ditriazinylamine type and the reaction of cyanuric chloride with ammonia yields N,N-bis(4,6-dichloro-s-triazin-2-yl)- or tris(4,6-dichloro-s-triazin-2-yl)amine.     

Cyanuric chloride catalyzed mild protocol for synthesis of biologically active dihydro/spiro quinazolinones and quinazolinone-glycoconjugates

We have developed an efficient cyanuric chloride (2,4,6-trichloro-1,3,5-triazine, TCT) catalyzed approach for the synthesis of 2,3-dihydroquinazolin-4(1H)-one (3a-3x), 2-spiroquinazolinone (5, 7), and glycoconjugates of 2,3-dihydroquinazolin-4(1H)-one (10a, 10b) derivatives. The reaction allows rapid cyclization (8-20 min) with 10 mol % cyanuric chloride to give skeletal complexity in good to excellent yield. We believe that this novel procedure may open the door for the easy generation of new and bioactive quinazolinones.     

Multicomponent Molecular Systems Based on Porphyrins, 1,3,5-Triazine and Carboranes: Synthesis and Characterization

2,4,6-Trichloro-1,3,5-triazine (cyanuric chloride) is an excellent coupling reagent for the preparation of highly structured multifunctional molecules. Three component systems based on porphyrin, cyanuric chloride and carborane clusters were prepared by a one-pot stepwise amination of cyanuric chloride with 5-(4-aminophenyl)-10,15,20-triphenylporphyrin, followed by replacement of the remaining chlorine atoms with carborane S- or N-nucleophiles. Some variants of 1,3,5-triazine derivatives containing porphyrin, carborane and residues of biologically active compounds such as maleimide, glycine methyl ester as well as thioglycolic acid, mercaptoethanol and hexafluoroisopropanol were also prepared. A careful control of the reaction temperature during the substitution reactions will allow the synthesis of desired compounds in a good to high yields. The structures of synthesized compounds were determined with UV-vis, IR, ¹H NMR, ¹¹B NMR, MALDI-TOF or LC-MS spectroscopic data. The dark and photocytotoxicity as well as intracellular localization and photoinduced cell death for compounds 8, 9, 17, 18 and 24 were evaluated.     

On the kinetics and energetics of one-electron oxidation of 1,3,5-triazines

One-electron oxidation of 1,3,5-triazines is observed with both excited uranyl ion (*UO2(2+)) and sulfate radical anion (SO4.-) in aqueous solution, but not with Tl2+, indicating that the standard reduction potentials E degree of 1,3,5-triazine radical cations are = 2.3 +/- 0.1 V vs. NHE, consistent with theoretical calculations; this suggests that if triazines inhibit electron transfer during photosynthesis, they would need to act on the reductive part of the electron transport chain.     

Heterocyclen, 73. Mitt.: Synthesen einiger substituierter 1,3,5-Triazine und Imidazo[1,2-a]-[1,3,5]-triazine

Zusammenfassung Substituierte 1,3,5-Triazine mit verschiedenen funktionellen Gruppen wurden synthetisiert und einige Azido-1,3,5-triazine wurden aufeine denkbare Azido—Tetrazol-Valenz-Isomerisierung untersucht; nur die Azid-Form konnte jedoch nachgewiesen werden. Von einigen Amino-1,3,5-triazinen ausgehend, gelang die Synthese von substituierten Imidazo[1,2-a]-[1,3,5]-triazinen.

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Heterocycles, LXXIII: Synthesis of some substituted 1.3.5-triazines and imidazo[1,2-a]-[1.3.5]-triazines

The synthesis of 1.3.5-triazines carrying various functional groups is described. 1.3.5-triazines with azido groups were studied for possible azido-tetrazolo valence isomerization; however, only the azido form could be detected. Some amino-1.3.5-triazines were used as starting material for the synthesis of substituted imidazo[1,2-a]-[1.3.5]-triazines. *** DIRECT SUPPORT *** A3615139 00009

     

Microwave Assisted Synthesis of Triaryl Cyanurates

Rapid synthesis of triarylcyanurates (2,4,6-triaryloxy-1,3,5-triazine) was carried out by reacting cyanuric chloride with the sodium salt of hydroxyaryl compounds in water using focused microwaves. Environmentally friendly procedure and isolation of pure products in excellent yields are important features of this method.     

Heterogeneous photocatalytic transformations of s-triazine derivatives

Photocatalytic processes arising from irradiated semiconductor oxide suspensions containing 1,3,5-triazine (s-triazine) derivatives are described. Whereas unsubstituted 1,3,5-triazine undergoes hydrolysis, irrespective of the presence of the photocatalyst, other chloro-, amino-, mercapto-, allyloxo-, carboxy- derivatives give rise, in the presence of band-gap excited semiconductor oxide, to nearly stoichiometric formation of 2,4,6-trihydroxy-1,3,5-triazine (cyanuric acid). This last compound is stable toward photocatalytic conditions as well as to ^·OH chemically generated in homogeneous solution (H₂O₂/UV or Fenton's reagent). Only partial conversion in cyanuric acid is observed for 2,4,6-tris(2-pyridyl)-1,3,5-triazine and possible explanation is given. The formation of inorganic species (nitrate, chloride, sulfate and ammonium ions) is reported and the mechanism of their evolution presented.     

2,4,6-Trichloro-1,3,5-triazine as an Efficient Catalyst for Synthesis of Benzopyran Derivatives under Solvent-Free Conditions

An efficient and convenient procedure has been developed for the synthesis of benzopyran derivatives by one-pot condensation of substituted salicyaldehydes and substituted 1,3-hexanediones in the presence of a catalytic amount of 2,4,6-trichloro-1,3,5-triazine (TCT, cyanuric chloride) under solvent-free conditions.