Organometallic alkylation of 2-chloro-4,6-dimethoxy-1,3,5-triazine: a study

The reactivity of 2-chloro-4,6-dimethoxy-1,3,5-triazine (1) has been investigated in Pd- or Ni-catalyzed cross-coupling processes with organostannanes, Grignard reagents, organoalanes and organozinc halides. All organometallic reagents considered form new C-C bonds on the heteroaromatic ring and afford the corresponding 2-alkyl-4,6-dimethoxy-1,3,5-triazines in moderate to very good yields. The collected data allows the choice of the alkylating agent as well as the experimental conditions depending on the residue to transfer.     

Direct synthesis of 2-oxazolines from carboxylic acids using 2-chloro-4,6-dimethoxy-1,3,5-triazine under mild conditions

2-Acyloxy-4,6-dimethoxy-1,3,5-triazines obtained from carboxylic acids and 2-chloro-4,6-dimethoxy-1,3,5-triazine were subsequently treated with 2-amino-2-methyl-1-propanol to afford the corresponding 2-oxazolines in excellent yield at room temperature.     

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,     

An Improved Procedure for the Large Scale Preparation of 2-Chloro-4,6-dimethoxy-1,3,5-triazine

A robust process for the preparation of multikilogram quantities of 2-chloro-4,6-dimethoxy-1,3,5-triazine (1) is described.     

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.     

A novel generation of coupling reagents. Enantiodifferentiating coupling reagents prepared in situ from 2-chloro-4,6-dimethoxy-1,3,5-triazine (CDMT) and chiral tertiary amines

Coupling of racemic N-protected amino acids with amino components by means of 2-chloro-4,6-dimethoxy-1,3,5-triazine (CDMT) in the presence of chiral tertiary amines such as strychnine, brucine, and sparteine proceeds enantioselectively, affording appropriate amides or dipeptides in 69-85% yield. The configuration of the preferred enantiomer and enantiomeric enrichment depend on the structures of the amine and carboxylic acid. Calculated Kagan enantioselectivity parameters (s) are in the range 1.6-195. Chiral triazinylammonium chlorides formed in situ from CDMT and chiral tertiary amines are postulated as reactive intermediates involved in the process of enantioselective activation of N-protected amino acids.     

Mass spectrometric study of 2-acyloxy-4,6-dimethoxy-1,3,5-triazines

Electron impact ionization mass spectra of 2-acyloxy-4,6-dimethoxy-1,3,5-triazines were examined. Two general pathways of fragmentation were found: (i) formation of an acylium ion typical for all the compounds studied, and (ii) rearrangement followed by loss of carbon monoxide, characteristic of derivatives of aromatic carboxylic acids.     

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.     

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.     

2-chloro-4,6-disubstituted-1,3,5-triazines a novel group of condensing reagents

The title, compounds form in reaction with carboxylic acids highly reactive intermediates, which are useful as acylating reagents in the preparation of esters, amides, acid anhydrides, and peptides in 64–98% yield.     

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.     

NMR studies of the dynamic behavior of 2-anilino-6-chloro-4-methoxy-1,3,5-triazine in solution

2-Anilino-6-chloro-4-methoxy-1,3,5-triazine was synthesized and studied by dynamic NMR. The activation parameters of hindered internal rotation in unsymmetrically substituted arylamino-sym-triazine were determined for the first time. It was found that a sterically more hindered rotational isomer is thermodynamically more stable in this compound (slow-exchange NOE data).     

2-氯-4,6-二苯氨基-1,3,5-三嗪改性纤维素的制备、结晶结构与水解性能

目前, 纤维素水解产生可发酵糖的效率很低, 是纤维素-乙醇转化的瓶颈问题. 拟以化学改性的方法改变纤维素结晶结构从而提高其水解效率. 首先以三聚氰氯(TCT)、苯胺为原料, 合成2-氯-4,6-二苯氨基-1,3,5-三嗪(DACT), 通过红外光谱、核磁共振谱图表征其结构. 将DACT用于微晶纤维素羟基的修饰, 并将修饰后的纤维素于50 ℃、固液比为1∶20 (W/V)比为条件下用70 wt%硫酸水解60 min, 研究DACT用量对纤维素结晶结构和水解性能的影响. 水解实验结果表明DACT的相对物质的量的百分含量(以葡萄糖环计)为30%左右时, 改性纤维素经酸催化水解后还原糖得率最高, 广角X射线衍射证实该水解结果可归因于化学改性令纤维素的结晶结构发生变化, 利于纤维素水解产生可发酵糖.     

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...