Zum Reaktionsverhalten von 2,4-Dioxohexahydro-1,3,5-triazin

Summary 2,4-Dioxohexahydro-1,3,5-triazin (DHT) reacts with formaldehyde and secondary amines (Mannich reaction) to the corresponding 1,3,5- or 1,5-aminomethyl-DHTs (1a–8a or1b–11b).DHT and formaldehyde give the methylol compounds12a,12b, and12c. Alkylation ofDHT with alkyl halides in presence of base and dimethyl-sulfoxide as the solvent affords the tri-N-alkyl derivatives14–22. 1,5-Dimorpholinomethyl-DHT (1b) can be alkylated in position 3 with alkyl halides. The morpholinomethyl groups in positions 1 and 5 behave as protecting groups and are easily removable. Thus, it is possible to introduce different alkyl substituents into the molecule. The reaction of1b with dihaloalkanes results in a coupling of twoDHT moleculesvia the nitrogen in position 3 (compounds26–29).

Herrn Professor Dr. mult.Friedrich Asinger zum 90. Geburtstag gewidmet     

Reaction of vinylpyridines and vinylquinolines with 1,3,5-triazine in polyphosphoric acid

Russian Journal of Organic Chemistry -     

Crystalline and molecular structure of 2,4-diamino-6-dinitromethyl-1,3,5-triazine potassium salt

An X-ray diffraction study of 2,4-diamino-6-dinitromethyl-1,3,5-triazine potassium salt is reported. Crystals are monoclinic: a = 7.697(2) Å, b = 11.147(2) Å, c = 12.612(4) Å, β = 117.95(2)°, V = 955.9(4) ų, space group P2₁/c; Z = 4, ρ_calc = 1.885 g/cm³. The compound crystallizes as a crystalline hydrate with one molecule of water. Anion consists of two planar fragments: dinitromethyl and diamino-1,3,5-triazine, the geometrical parameters of which were analyzed. The coordination of potassium cations and multiple hydrogen bonds leading to the formation of a complex three-dimensional skeleton has been detected.     

A new method for the synthesis of 2,4-diazido-6-trinitromethyl-1,3,5-triazine

A new method for the synthesis of 2,4-diazido-6-trinitromethyl-1,3,5-triazine was elaborated. The method makes it possible to exclude the work with unstable 2,4,6-tris(trinitromethyl)-1,3,5-triazine.     

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.     

Synthesis and In vitro Study of Cytotoxic Activity of New Tetrazole-Containing 2,4-Diamino-1,3,5-triazine Derivatives

Russian Journal of General Chemistry - New tetrazole-containing derivatives of 2,4-diamino-1,3,5-triazine were synthesized. The cytotoxic activity of the obtained compounds against Huh-7 and HeLa...     

Study on the 1,3,5-triazine gamma-radiolysis

Triazines are a class of molecules which have been found in meteorites such as Orgueil meteorite. Despite their poor resistance to UV radiation, these molecules survived millions of years inside a meteorite. The present work is dedicated to the examination of the radiation resistance of the simplest sym-triazine: 1,3,5-triazine. The crystals of this molecule have been irradiated with γ-radiation at 50 and 350 kGy and were studied by electronic absorption spectroscopy, liquid chromatography, FT-IR spectroscopy and differential scanning calorimetry (DSC). All the data suggest the relatively low stability of this molecule to high energy radiation. The resulting products from radiolysis are formamidine together with triazine dimers and oligomers. Other radiolysis products are H₂, CH₄, HCN and other gases.     

Reaction of 2,4,6-trichloro-1,3,5-triazine with nucleophilic reagents in the presence of tertiary amines

A mechanism for the nucleophilic substitution of halogen in cyanuric chloride in the presence of tertiary amines is proposed. When carboxylic acids react with cyanuric chloride in the presence of tertiary amines, quaternary acylammonium salts are formed which can be used as acylating agents.     

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.