Synthesis of new 1,3,5-thiadiazine and 1,3,5-triazine derivatives and their antimicrobial activity

Interaction of ethyl chloroformate with γ-N-substituted trithioallophanic acids has been found to yield the corresponding 6-oxo-5-aryl-2,4-dithio-hexahydro-l,3,5-thiadiazines. These on reaction with amines yield 1,3,5-triazines. γ-N-substituted β-oxo-dithio-allophanic acid with ethyl chloroformate similarly yields 4,6-dioxo-5-aryl-2-thio-1,3,5-thiadiazine. Antimicrobial activity of thiadiazines has been reported.     

Synthesis and spectroscopic studies of some fluorinated 1,3,5-triazine derivatives

Tri-substituted derivatives of 2,4,6-trichloro-1,3,5-triazine have been prepared in good yields by the reaction of 2,4,6-trichloro-1,3,5-triazine with various aromatic amines. These new types of products have been characterised by elemental analysis, IR, ¹H and ¹⁹F NMR spectral studies.     

Synthesis and antitumor activity of benzimidazolyl-1,3,5-triazine and benzimidazolylpyrimidine derivatives

Triamino-substituted 1,3,5-triazine and pyrimidine derivatives were synthesized and tested for antitumor activities using some human cancer cell lines and murine leukemia cell lines. All the compounds having benzimidazolyl and morpholino groups as substituents on the 1,3,5-triazine ring showed antitumor activity. Pyrimidine derivatives having the same groups as substituents also showed antitumor activity. Among them, the compounds having 1-benzimidazolyl, morpholino and cis-2,3-dimethylmorpholino groups as substituents on the 1,3,5-triazine ring or pyrimidine ring exhibited the most potent antitumor activity, and these compounds exhibited no or very weak aromatase inhibitory activity. In contrast, the compounds having imidazolyl group instead of benzimidazolyl group as a substituent on the 1,3,5-triazine ring showed a potent aromatase inhibitory activity.     

2-nitroguanidine derivatives: X. Synthesis and nitration of 4-nitriminotetrahydro-1,3,5-oxadiazine and 2-nitriminohexahydro-1,3,5-triazine and their substituted derivatives

A new synthetic procedure was developed to obtain 1-hydroxymethyl-2-nitroguanidine from 2-nitroguanidine and formaldehyde without catalyst. Reactions of 2-nitroguanidine and its 1-methyl-and 1-phenylsubstituted derivatives with formaldehyde and urotropin under acid catalysis resulted in 4-nitriminotetrahydro-1,3,5-oxadiazine and 2-nitriminohexahydro-1,3,5-triazine and their methyl-and phenyl-substituted derivatives, whose nitration with concn. HNO₃ in the presence of acetic anhydride and concn. H₂SO₄ depending on the temperature conditions led to the formation of 4-nitrimino-3,5-dinitrotetrahydro-1,3,5-oxadiazine, 3-methyl-4-nitrimino-5-nitrotetrahydro-1,3,5-oxadiazine, 2-nitrimino-5-nitrohexahydro-1,3,5-triazine, and 1,3,5-trinitro-hexahydro-1,3,5-triazine-2-one.     

Synthesis of 2,4,6-triphenyl-1,3,5-triazine

Conclusions A study was made of the cyclotrimerization of benzonitrile in chlorosulfonic acid and the optimum conditions were ascertained for the formation of 2,4,6-triphenyl-1,3,5-triazine.Translated from Izvestiya Akademii Nauk SSSR, Seriya Khimicheskaya, No. 9, pp. 2105, September, 1972.     

2-氯-4,6-二(2-萘氧基)-1,3,5-三嗪的合成及性能

1,3,5-三嗪（均三嗪）衍生物一般是由三聚氯氰与-OH、-NH2、-SH、-NHR等含活泼氢的化合物反应得到。由于三聚氯氰上三个氯原子具有反应分级可控性,以及这类衍生物具有良好的热稳定性、光活性和生物活性,因此均三嗪衍生物受到了广泛关注。含萘氧基的均三嗪衍生物是其中重要的一部分。这部分衍生物中以一取代和三取代物研究得较多,王巧峰,江璐霞等合成了萘酚取代三聚氯氰上一个氯的产物,     

含均三嗪结构甲氧基丙烯酸酯化合物的合成及抑菌活性研究

采用亲核取代和消除反应,合成了7个含均三嗪结构的新型甲氧基丙烯酸酯化合物,目标化合物的结构经IR、1H NMR、HRMS进行表征。对目标化合物进行了真菌抑制活性实验,结果表明在50ug·m L-1浓度下,4个目标化合物表现出一定的真菌抑制活性。     

The ultrafast dynamics and nonlinear optical properties of tribranched styryl derivatives based on 1,3,5-triazine

By using the femtosecond laser spectroscopic techniques, we have studied the ultrafast response and the nonlinear optical properties of three molecules with donor-acceptor structure (denoted as T01, T02, and T03). Two-photon absorption (2PA) cross sections measured by the open aperture Z-scan technique were determined to be 77, 90, and 410 GM for T01, T02, and T03, respectively. The relaxation dynamics of the excited states were measured by two-color femtosecond pump-probe and time-resolved photoluminescence (PL) experiments. By changing the solvent from chloroform (CHCl3) to dimethyl sulfoxide (DMSO), the transient dynamics was found changed significantly and the decay time of PL emission decreased dramatically because DMSO with large dipole moment accelerates the cross-transfer process and the nonradiative process in the molecules.     

Synthesis, crystal structures, electrochemical and spectroscopic properties of ruthenium(II) complexes containing diamino-1,3,5-triazine derivatives

Three Ru(II) complexes [Ru(bpy)₂(1-IQTNH)](ClO₄)₂ (1), [Ru(bpy)₂(2-QTNH)](ClO₄)₂ (2) and [Ru(bpy)₂(3-IQTNH)](ClO₄)₂ (3) (bpy = 2,2′-bipyridine, 1-IQTNH = 6-(isoquinolin-1-yl)-1,3,5-triazine- 2,4-diamine, 2-QTNH = 6-(quinolin-2-yl)-1,3,5-triazine- 2,4-diamine, 3-IQTNH = 6-(isoquinolin-3-yl)-1,3,5-triazine-2,4-diamine) have been synthesized and characterized by elemental analysis, ¹H NMR spectroscopy, electrospray ionization mass spectrometry and X-ray crystallography. The electrochemical and spectroscopic properties of the complexes differ from those of [Ru(bpy)₃]²⁺ owing to the structural differences between the ligands and their complexes.     

Synthesis of 2-trifluoromethyl-4,6-diphenyl-1,3,5-triazine

Conclusions Methods have been developed for the preparation of the simplest fluorine-containing phenyltriazine, viz., 2-trifluororaethyl-4,6-diphenyl-1,3,5-triazine, in virtually quantitative yield.Translated from Izvestiva Akademii Nauk SSSR, Seriya Khimieheskaya, No. 4, pp. 919–920, April, 1986.     

Trisubstituted 1,3,5-Triazines. 6. Synthesis of 2,4,6-Tris(acetonyl)-1,3,5-triazine

Acylation of 2,4,6-tris(tert-butoxycarbonylmethyl)-1,3,5-triazine with acetic anhydride in the presence of lithium hydride with subsequent removal of the tert-butoxycarbonyl groups with trifluoroacetic acid leads to 2,4,6-tris(acetonyl)-1,3,5-triazine, the cyclic analog of -cyanoacetone. The special spectral features of this compound compared with triazines obtained previously are discussed.     

Computational insight into energetic cage derivatives based on hexahydro-1,3,5-trinitro-1,3,5-triazine

Four novel cage compounds were designed by introducing –N(NO₂)CH₂–, –N(NO₂)O–, –N(NO₂)N(NO₂)–, and –N=N– linkages into the RDX (hexahydro-1,3,5-trinitro-1,3,5-triazine) skeleton. Their molecular geometry, electronic structure, heat of formation, and detonation properties were systematically studied using density functional theory (DFT). In addition, the most stable dimers of the four compounds were constructed to further investigate their stability based on intermolecular interactions. It is found that the unconventional CH⋯O interactions would be the dominant driving force when the title compounds form crystals. Compared with the traditional explosives, the compounds with higher detonation properties and lower impact sensitivity will be considered as promising candidates for high energy density compounds. Our results indicate that our innovative design strategy is extremely useful for developing novel energetic compounds.     

A simple preparation of 1,3,5-triazine derivatives from 4-pyridones

The reaction of 4-pyridone or 4-quinolone with methyl or benzyl isocyanate in the presence of triethylamine or 1,1,3,3-tetramethylguanidine base gave the corresponding 1,3,5-triazine derivative (e. g., II) in a good yield via stepwise additions.     

Synthesis of new microsensor coatings and their response to test vapors 2,4,6-trisubstituted-1,3,5-triazine derivatives

Novel 1,3,5-triazine derivatives were spray-coated onto surface acoustic wave (SAW) devices and exposed to vapors of dimethyl methylphosphonate (DMMP), chloroethyl ethyl sulfide (CEES) and water. Changes in chemiresistor and SAW responses were monitored and recorded by computer-controlled data-acquisition techniques. All the derivatives tested showed little or no chemiresistor or SAW responses to water vapor. The largest reversible chemiresistor response to DMMP vapor was observed with the dicarboxylic acid derivative. The largest SAW response to DMMP was with the dithione, and the dichloro-octylthio derivative showed the largest response to CEES.     

Synthesis of 1,3,5-triazine derivatives on the basis of carboxylic acid imino esters (review)

Data on methods for the synthesis of 1,3,5-triazine derivatives by cyclotrimerization and cyclocondensation reactions with the participation of carboxylic acid imino esters are systematized in the review.Translated from Khimiya Geterotsiklicheskikh Soedinenii, No.12, pp. 1587–1605, December 1992.     

Trisubstituted 1,3,5-triazines. 4. Synthesis of 2-nitroamino-4,6-bis(trinitromethyl)-1,3,5-triazine

The nitration, at the amino group, of 2-amino-4,6-bis(trinitromethyl)-1,3,5-triazine and its derivatives has been studied.For Communication 3, see [1].n. D. Zelinskii Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, 117913. Institute of Chemical Physics in Chernoglovka, Chernoglovka, Moscow Oblast, 142432, Russia. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 79–81, January, 1999.