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Chesniuk, A. A.; Mikhailichenko, S. N.; Zavodnov, V. S.; Zaplishny, V. N.

doi:10.1023/a:1015335124677

Cited by 8 publications

(8 citation statements)

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“…Compounds IIIc and IVc have the maximum intensity of the molecular ions. The fragmentation pattern of the molecular ions under electronic impact is the same as has been observed for the synthesized heterocyclic derivatives of the 1,3,5-triazine [36,37,[40][41][42][43].…”

Section: Resultsmentioning

confidence: 55%

“…It was possible to synthesize THA using esters III as intermediate compounds. This could be achieved using 4,6 disubstituted-2-(trimethylamino) chlorides I as initial compounds [36,37]. Unfortunately, the attempts to synthesize esters III with direct reaction between quaternary salts I and some esters of oxycarboxylic acids were not successful probably due to the relatively low nucleophilicity of the hydroxy group in these acids.…”

Section: Resultsmentioning

confidence: 99%

“…We found that alkylation of oxo-derivatives II is the most convenient and successful method for the esters (III) synthesis. Compounds II could be easily synthesized by the basic hydrolysis of quaternary salts [36].…”

Section: Resultsmentioning

confidence: 99%

“…The progress of the reactions was monitored and the purities of the compounds were checked by TLC on Polymer2 with UV sensitive silufol layer plates in a acetone:hexane (1:1) system. The initial 2,4-disubstituted-6-chloro-1,3,5-triazines, starting ammonium salts (I) and oxocompounds (II) were prepared from cyanuric chloride according to the procedures described earlier [2,7,36,37]. The solvents have been purified and dried according to the procedures as described earlier [38,39].…”

Section: Instrumentation and Materialsmentioning

confidence: 99%

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Synthesis of new 4,6-disubstituted-1,3-5-triazin-2-yloxy esters and N-hydroxyamides

et al. 2010

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A convenient method for synthesis of new sym-triazine ester and hydroxamate derivatives has been developed. Various reaction conditions were studied and optimized, and a series of new 1,3,5-triazine based esters and N-hydroxyamides were obtained with good yields (38-80%). The reaction between oxo-derivatives of 4,6-disubstituted-1,3,5-triazines and halogenated carboxylic esters derivatives using Cs2CO3 as a catalyst was found to be the most convenient method for 4,6-disubstituted-1,3,5-triazine-2-yloxy esters synthesis. These 1,3,5-triazin based esters served as precursors for the synthesis of 4,6-disubstituted-1,3,5-triazin-2-yloxy-N-hydroxybutanamides using solution of hydroxylamine hydrochloride in dry methanol and KOH at room temperature. Structures of the newly synthesized compounds were obtained by 1 H NMR, 13 C NMR, MS, IR spectral data and elemental analysis.

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Section: Resultsmentioning

confidence: 55%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Instrumentation and Materialsmentioning

confidence: 99%

See 2 more Smart Citations

Synthesis of new 4,6-disubstituted-1,3-5-triazin-2-yloxy esters and N-hydroxyamides

et al. 2010

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“…[9][10][11][12] We found catalytic dehydrocondensation involving the in situ generation of DMT-Am from a stoichiometric amount of 2-chloro-4,6-dimethoxy-1,3,5-triazine (CDMT) and a catalytic amount of a tert-amine, as summarized in Chart 1. 13) In this system, the addition of a base, proton capture agent (PCA), 14) which is inert toward CDMT, is essential for the regeneration of the tert-amine from its hydrochloride.…”

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confidence: 98%

Study of 1,3,5-Triazine-Based Catalytic Amide-Forming Reactions: Effect of Solvents and Basicity of Reactants

Kunishima

Kitamura

Tanaka

et al. 2013

CHEMICAL & PHARMACEUTICAL BULLETIN

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Effect of the basic property of reactants (tertiary amine catalysts, a substrate amine, and acid neutralizers) on catalytic dehydrocondensation between a carboxylic acid and an amine by using 2-chloro-4,6-dimethoxy-1,3,5-triazine (CDMT) was studied. The reaction yield was affected by the acid-base equilibrium among reactants. In dichloromethane, a representative aprotic solvent, a strongly basic catalyst gave amides in higher yields than weakly basic catalysts, regardless of the basicity of the acid neutralizer, which is called the proton capture agent (PCA). In contrast, in protic solvents, such as methanol or aqueous methanol, weakly basic catalysts gave amides in somewhat better yields than the strongly basic catalysts. In general, PCAs with weakly basic properties are favorable, because those with strongly basic properties tend to give byproducts arising from the reaction between CDMT and the substrate amine.Key words amide; dehydrocondensation; 1,3,5-triazine; catalytic reaction; solvent effect Dehydrocondensation to form amides and esters is an essential tool for organic and medicinal chemists, and various dehydrocondensing reagents have been developed for the past several decades.1,2) Among them, 4-(4,6-dimethoxy-1,3,5-triazin-2-yl)-4-methylmorpholinium chloride (DMT-MM, Fig. 1), has proven to be useful because of its stability, reactivities, and low synthetic cost. [3][4][5] In particular, it selectively produces amides from carboxylic acids and amines even in alcoholic or aqueous media.6-8) Related triazine-based compounds, N- (4,6-dimethoxy-1,3,5-triazin-2-yl)-N,N,N-trialkylammonium chloride (DMT-Ams), which consist of tertiary amines (tertamine) instead of N-methylmorpholine (NMM), have a similar reactivity for dehydrocondensation. [9][10][11][12] We found catalytic dehydrocondensation involving the in situ generation of DMT-Am from a stoichiometric amount of 2-chloro-4,6-dimethoxy-1,3,5-triazine (CDMT) and a catalytic amount of a tert-amine, as summarized in Chart 1. 13) In this system, the addition of a base, proton capture agent (PCA), 14) which is inert toward CDMT, is essential for the regeneration of the tert-amine from its hydrochloride.From this understanding, we have developed catalytic dehydrocondensing reactions using a tert-amine with a specific functional property, such as molecular recognition.13,15-19) As functionalized catalysts, we employed an N,N-dimethylglycine ester as a catalytic tert-amine part because of its facile introduction into functional molecules via the ester group and also because of its potent catalytic activity in a protic solvent. However, the details of the choice of catalytic tert-amine parts depending on the reaction conditions have not been described.Very recently, we have studied the structure-reactivity relationship of tert-amines reacting with CDMT for the generation of DMT-Am, and proposed the gauche β-alkyl group effect.12) This effect indicates that a steric environment around the nitrogen atom rather than the basicity of the tert-amines is predominantly c...

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Sodium Sulfide

Dittmer¹,

Avilov²

2006

Encyclopedia of Reagents for Organic Synthesis

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Cited by 8 publications

References 1 publication

Synthesis of new 4,6-disubstituted-1,3-5-triazin-2-yloxy esters and N-hydroxyamides

Synthesis of new 4,6-disubstituted-1,3-5-triazin-2-yloxy esters and N-hydroxyamides

Study of 1,3,5-Triazine-Based Catalytic Amide-Forming Reactions: Effect of Solvents and Basicity of Reactants

Sodium Sulfide

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