Synthesis,structures, and properties of bis(4,6-disubstituted 1,3,5-triazin-2-yl) ethers

Reactions of (4,6-disubstituted 1,3,5-triazin-2-yl)trimethylammonium chlorides with glycine sodium salt in the presence of Et₃N afforded bis(triazin-2-yl) ethers instead of the expected triazinylaminoacetic acids. The structures of the resulting compounds were established by the independent synthesis, spectroscopic data, and X-ray diffraction analysis.     

4-(9-蒽基)-6-十六烷氧基-2-氨基-1,3,5-三嗪的合成及光谱行为的研究

从三氯均三嗪出发通过三步反应合成了4-(9-蒽基)-6-十六烷氧基-2-氨基-1,3,5-三嗪(AHTA),并通过红外、核磁、质谱、高分辨质谱对目标产物进行了表征.研究表明AHTA分子在基态下分子的蒽环与三嗪环不共平面,激发态下表现为ICT的荧光发射.由于分子间氢键作用的存在,AHTA在自组装膜和LB膜中均形成H-聚集体.     

Synthesis and structural study of 4,6-diazido-2-(2,2,2-trinitroethylamino)-1,3,5-triazine

Russian Chemical Bulletin - A method for synthesis of 2-(2,2,2-trinitroethylamino)-4,6-diazido-1,3,5-triazine from 2-amino-4,6-diazido-1,3,5-triazine was elaborated. The molecular and crystal...     

4-(9-蒽基)-6-辛氧基-1,3,5-三嗪-2-胺的合成及其在酸性介质中的光谱行为研究

以2,4-二氯-6-辛氧基-1,3,5-三嗪为原料,经Kumada偶联及胺化两步反应合成了三嗪胺衍生物:4-(9-蒽基)-6-辛氧基-1,3,5-三嗪-2-胺(AOOTA),总产率为38%.通过紫外-可见吸收光谱及荧光光谱研究了氯仿溶液中AOOTA在乙酸(HOAc)及三氟乙酸(TFA)作用下的光谱行为.研究发现AOOTA与HOAc在基态及激发态下均不能发生双氢键作用,而AOOTA与TFA相互作用基态下形成双氢键复合物,激发态下由于分子中蒽基及辛氧基与三嗪环间的C-C单键以及C-O单键的自由旋转,从而使得AOOTA与TFA分子间不能形成有效的氢键相互作用.     

Synthesis and characterization of two cobalt(II) complexes based on 4,6-bis(2-pyridyl)-1,3,5-triazin-2-ol

Two cobalt(II) complexes based on 4,6-bis(2-pyridyl)-1,3,5-triazin-2-ol (HOBPT), [Co₃(OBPT)(μ³?OH)(SO₄)₂(H₂O)₃]·2H₂O (1) and [Co(OBPT)₂]·2H₂O (2) were obtained. Single-crystal X-ray diffraction analyses indicate that 1 is a two-dimensional (2D) structure and the ligand adopts mono/bis-bidentate coordination; this coordination mode of this ligand was never found before. Magnetic properties of 1 have been studied, showing that 1 is a spin canted belt. Much different from 1, 2 is a discrete structure with tridentate ligand with its hydroxyl group deprotonated but uncoordinated. Lattice water molecules in 2 link to four-membered water clusters, which linked the [Co(OBPT)₂] to 1-D chains along the b axis.     

Preparation of Weinreb amides using 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMT-MM)

Weinreb amides were successfully prepared from the corresponding carboxylic acids using 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMT-MM) in the solvents, methanol, isopropyl alcohol, and acetonitrile, which can solubilize DMT-MM. A variety of carboxylic acids were converted to the corresponding Weinreb amides in excellent yields by simply mixing with DMT-MM and N,O-dimethylhydroxylamine hydrochloride.     

Synthesis of 2-(4,6-dimethoxy-1,3,5-triazin-2-yloxyimino) derivatives: application in solution peptide synthesis

A new class of 1,3,5-triazinyloxyimino derivatives were prepared, characterized and tested for reactivity in solution peptide synthesis. The new triazinyloxyimino derivatives failed to activate the carboxyl group during formation of peptide bonds, but gave the corresponding N-triazinyl amino acid derivatives as a major product. The oxyma (ethyl 2-cyano-2-(hydroxyimino)acetate) uronium salt was superior to other uronium salts in terms of racemization, while 2-chloro-4,6-dimethoxy-1,3,5-triazine (CDMT, 9) gave the best results.     

A racemization test in peptide synthesis using 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMT-MM)

Racemization of the C-terminal amino acid (Ala) has been studied in various solvents during coupling between 4-methoxybenzyloxycarbonyl (Z(OMe))-Gly-L-Ala-OH and phenylalanine benzyl ester (H-Phe-OBzl) with 4-(4,6-dimethoxy-1,3,5-thiazin-2-yl)-4-methylmorpholinium chloride (DMT-MM). The reaction occurred without substantial racemization in AcOEt, tetrahydrofuran (THF), N,N-dimethylformamide (DMF), CH3CN, and 2-PrOH, while a slight racemization was observed in dimethyl sulfoxide (DMSO), EtOH, and MeOH. The extent of racemization may correlate with the polarity of the solvents.     

Photophysical and Complexation Behavior of (4-Dimethylamino-benzylidene)-(4,6-dimethyl-pyrimidin-2-yl)-amine

The absorption and fluorescence characteristics of (4‐dimethylamino‐benzylidene)‐(4,6‐dimethyl‐pyrimidin‐2‐yl)‐amine (SB) have been investigated in different solvents. Both the absorption and emission spectra of SB exhibit red shifts as the solvent polarity increases. This indicats a change in dipole moment of molecules upon excitation as a result of intramolecular charge transfer interaction. The fluorescence quantum yield depends strongly on the properties of the solvents, which was discussed on the bases of positive and negative solvatokinetic effects. The effect of some divalent transition metal ions such as Mn²⁺, Co²⁺, Ni²⁺, Cu²⁺, Zn²⁺, Cd²⁺, and Hg²⁺on the absorption and fluorescence spectra of SB is also investigated. The results were consistent with formation of highly colored metal‐ SB complex which is responsible for the extreme quenching of the fluorescence of SB. The variations of both the formation constant of the complex and Stern‐Volmer constant were correlated with the electronic structure of the used metal ion.     

Synthesis and structures of 4,6-disubstituted 2-(5-methyl-1,2,4-oxadiazol-3-yl)-1,3,5-triazines

New 1,2,4-oxadiazolyl-1,3,5-triazines were synthesized from amidoximes derived from sym-triazine mononitriles. The structure of one of the resulting compounds was studied in detail by X-ray diffraction. __________ Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1845–1850, August, 2005.     

Synthesis of sterically-hindered peptidomimetics using 4-(4,6-dimethoxy-1,3,5-triazine-2-yl)-4-methyl-morpholinium chloride

Our study demonstrated that 4-(4,6-dimethoxy-1,3,5-triazine-2-yl)-4-methyl-morpholinium chloride (DMTMM) is a versatile coupling reagent for the synthesis of sterically-hindered peptidomimetics. It is superior to HBTU/HOBt and CDMT in controlling racemization and N-arylation, respectively.     

Synthesis and Crystal Structure of Diethyl (4,6-diamino-1,3,5-triazine-2-yl) phosphonate

1　INTRODUCTIONSomeoforganophosphoruscompounds,includingmanyheterocycliccompoundscontainingphosphonogroup,havegoodbioactivityinorganism[1].Duetotheirrela-tionwithbiochemical/biological,pharmacologicalandpesticidalresearch,hetero-cycliccompoundscontainingphosphonogrouphavebeensynthesizedbysomeofnewsyntheticmethods,inwhichseveralnewbuildingblockwereused,suchasβ-phos-phonicenemines,[2,3]isocyanomethylphosphonate,[4]β-functionalγ-oxo-alkylphos-phonates,[5]andacetylenicphosphonate.[6]Inourpr…     

Synthesis and structure of N-(4,6-dimethylpyrimidin-2-yl)-2-(5-phenyl-2H-tetrazol-2-yl)acetohydrazide and 1-(4,6-dimethylpyrimidin-2-yl)-3-[(5-phenyl-2H-tetrazol-2-yl)methyl]-1H-pyrazol-5-ol

Russian Journal of Organic Chemistry - New tetrazolyl derivatives of pyrimidine were synthesized containing various linker groups. The structure of these compounds was established by NMR...     

A novel glycosyl donor for chemo-enzymatic oligosaccharide synthesis: 4,6-dimethoxy-1,3,5-triazin-2-yl glycoside

A novel activated glycosidic compound, 4,6-dimethoxy-1,3,5-triazin-2-yl beta-lactoside (DMT-beta-Lac), which can be prepared directly from lactose in water without using any protecting groups, was found to be an efficient glycosyl donor for enzymatic glycosylation catalyzed by an endo-1,4-beta-glucanase.