Synthesis of 4-amino-6-chloro-1,3,5-triazin-2(1H)-ones

Бахарев, В. В.; Гидаспов, А. А.; Parfenov, Victor E.; Ulˈyankina, I. V.; Zavodskaya, Anna V.; Selezneva, E. V.; Suponitskii, K. Yu.; Sheremetev, Aleksei B.

doi:10.1007/s11172-012-0015-8

Cited by 10 publications

(7 citation statements)

References 58 publications

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“…Cyanuric chloride was first reacted with different amines such as benzylamine, N-methylbenzylamine, morpholine, piperidine, or methanol at 0 ∘ C for 1-2 h to afford the products a-e (Scheme 1); the spectral data agreed with the reported data [44,45]. The dichloro derivatives a-e were reacted with hydrazine hydrate (80%) under reflux using acetonitrile as a solvent to render the products of 2,4-dihydrazino-6-substituted-1,3,5-triazine derivatives a-e which were used directly in the next step without further purification (Scheme 1).…”

Section: Resultssupporting

confidence: 72%

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Synthesis, Characterization, and Antimicrobial Studies of Novel Series of 2,4-Bis(hydrazino)-6-substituted-1,3,5-triazine and Their Schiff Base Derivatives

Al-Rasheed

Sholkamy

Alshaikh

et al. 2018

Journal of Chemistry

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The present work represents the synthesis, characterization, and antimicrobial studies of novel series of 2,4-bis(hydrazino)-6substituted-1,3,5-triazine and their Schiff base derivatives. IR, NMR ( 1 H and 13 C), elemental analysis, and LC-MS characterized the prepared compounds. The biological activity of the target products was evaluated as well. Twenty-two of the prepared compounds were selected according to their solubility in aqueous DMSO. Only eight compounds showed good activity against the selected pathogenic bacteria and did not show antagonistic effect against fungus Candida albicans. Two compounds k and g have widerange effect presently in Gram-positive and Gram-negative bacteria while other compounds ( f, i, m, d, i, and h) showed specific effect against the Gram-negative or Gram-positive bacteria. The minimum inhibitory concentration (MIC, g/mL) of f, i, k, and h compounds against Streptococcus mutans was 62.5 g/mL, 100 g/mL, 31.25 g/mL, and 31.25 g/mL, respectively. The MIC of m, k, d, g, and h compounds against Staphylococcus aureus was 62.5 g/mL, 31.25 g/mL, 31.25 g/mL, 100 g/mL, and 62.5 g/mL, respectively. The MIC of k, g, and i compounds against Salmonella typhimurium was 31.25 g/mL, 100 g/mL, and 62.5 g/mL, respectively. The MIC of i compound against Escherichia coli was 62.5 g/mL.

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Section: Resultssupporting

confidence: 72%

“…were prepared according to the reported procedure with some modifications [21,44,45]. Hydrazine hydrate (80%) in 20 mL acetonitrile was added to a solution of a-e (20 mmol) in acetonitrile (50 mL) at room temperature.…”

Section: General Methods For the Synthesis Of 24-dihydrazino-6substitmentioning

confidence: 99%

Synthesis, Characterization, and Antimicrobial Studies of Novel Series of 2,4-Bis(hydrazino)-6-substituted-1,3,5-triazine and Their Schiff Base Derivatives

Al-Rasheed

Sholkamy

Alshaikh

et al. 2018

Journal of Chemistry

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“…13 (For a short description see Supplementary data). All other chemicals (reagent grade) were obtained from commercial sources and used without further purification.…”

Section: Generalmentioning

confidence: 99%

Synthesis of new 5-aza-isosteres of guanine—5-aminosubstituted 1,2,4-triazolo[1,5-a]-1,3,5-triazin-7-ones

et al. 2014

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“…The dimethoxy derivatives DMeCT 4 were prepared in the same way for prepation of 2 with a longer reaction time of reaction and heating in methanol for 4 h at 50 °C to afford the chloro-dimethoxy derivatives DMeCT 4 [32]. Reaction of 4 with hydrazine hydrate using ultrasonic irradiation at 60 °C afforded the expected product DMeHT 5 in an excellent yield and purity.…”

Section: Results and Discusionsmentioning

confidence: 99%

“…The product was prepared using the reported method [32] and obtained from CH 2 Cl 2 /hexane as a white solid in 96% yield; mp 73–75 °C [Lit. [32] mp 76–78 °C). 1 H-NMR (CDCl 3 ) δ 3.98 (s, 6H, 2OCH 3 ).…”

Section: Methodsmentioning

confidence: 99%

Hydrazino-methoxy-1,3,5-triazine Derivatives’ Excellent Corrosion Organic Inhibitors of Steel in Acidic Chloride Solution

et al. 2016

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Abstract:The corrosion inhibition performance of 2-hydrazino-4,6-dimethoxy-1,3,5-tirazine (DMeHT), 2,4-dihydrazino-6-methoxy-1,3,5-triaizine (DHMeT), and 2,4,6-tridydrazino-1,3,5-triaizne (TH 3 ) on steel corrosion in acidic media was examined using electrochemical techniques. The results showed 2,4-Ddihydrazino-6-methoxy-1,3,5-triaizine (DHMeT) gave the best corrosion protection performance among the other hydrazino derivatives even at a low concentration of 25 ppm (95%). The number of hydrazino groups play an important role in the corrosion inhibition, where the two hydrazine groups increased the electrostatic interactions between the protonated tested compounds, the negatively charged steel surface resulted from the adsorption of the chloride anions, and the presence of the methoxy group made the compound more reliable for formation of film protection on the surface of steel through the lone pair of oxygen atoms. Electrochemical Impedance Spectroscopy (EIS) measurements suggested that the corrosion process of steel in presence of the hydrazino-s-triazine derivatives (TH 3 , DMeHT and DHMeT) were being controlled by the charge transfer reaction. Polarization curves indicated that the examined TH 3 , DMeHT and DHMeT behaved as mixed type inhibitors.

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Synthesis of 4-amino-6-chloro-1,3,5-triazin-2(1H)-ones

Cited by 10 publications

References 58 publications

Synthesis, Characterization, and Antimicrobial Studies of Novel Series of 2,4-Bis(hydrazino)-6-substituted-1,3,5-triazine and Their Schiff Base Derivatives

Synthesis, Characterization, and Antimicrobial Studies of Novel Series of 2,4-Bis(hydrazino)-6-substituted-1,3,5-triazine and Their Schiff Base Derivatives

Synthesis of new 5-aza-isosteres of guanine—5-aminosubstituted 1,2,4-triazolo[1,5-a]-1,3,5-triazin-7-ones

Hydrazino-methoxy-1,3,5-triazine Derivatives’ Excellent Corrosion Organic Inhibitors of Steel in Acidic Chloride Solution

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