New Approach for the One-Pot Synthesis of 1,3,5-Triazine
Derivatives: Application of Cu(I) Supported on a Weakly Acidic
Cation-Exchanger Resin in a Comparative Study

J 2019

New Approach for the One-Pot Synthesis of 1,3,5-Triazine Derivatives: Application of Cu(I) Supported on a Weakly Acidic Cation-Exchanger Resin in a Comparative Study

HAVRÁNKOVÁ, Eva; Jozef CSÖLLEI a Pavel PAZDERA

Základní údaje

Originální název

New Approach for the One-Pot Synthesis of 1,3,5-Triazine Derivatives: Application of Cu(I) Supported on a Weakly Acidic Cation-Exchanger Resin in a Comparative Study

Autoři

HAVRÁNKOVÁ, Eva ; Jozef CSÖLLEI a Pavel PAZDERA

Vydání

Molecules, Basel, MDPI, 2019, 1420-3049

Další údaje

Jazyk

angličtina

Typ výsledku

Článek v odborném periodiku

Obor

10401 Organic chemistry

Stát vydavatele

Švýcarsko

Utajení

není předmětem státního či obchodního tajemství

Odkazy

Full Text

Impakt faktor

Impact factor: 3.267

Kód RIV

RIV/00216224:14310/19:00110875

Organizační jednotka

Přírodovědecká fakulta

DOI

https://doi.org/10.3390/molecules24193586

UT WoS

000496242300171

EID Scopus

2-s2.0-85072970633

Klíčová slova anglicky

1 3 5-triazine; supported Cu(I) catalyst; Ullmann reaction; one-pot synthesis

Štítky

rivok, ÚChL

Příznaky

Mezinárodní význam, Recenzováno

Změněno: 3. 3. 2021 12:29, Mgr. Hana Hurtová

Anotace

V originále

An efficient and simple methodology for Ullmann Cu(I)-catalyzed synthesis of di- and trisubstituted 1,3,5-triazine derivatives from dichlorotriazinyl benzenesulfonamide and corresponding nucleophiles is reported. Cations Cu(I) supported on macroporous and weakly acidic, low-cost industrial resin of polyacrylate type were used as a catalyst. The reaction times and yields were compared with traditional synthetic methods for synthesis of substituted 1,3,5-triazine derivatives via nucleophilic substitution of chlorine atoms in dichlorotriazinyl benzenesulfonamide. It was found that Ullmann-type reactions provide significantly shortened reaction times and, in some cases, also higher yields. Finally, trisubstituted s-triazine derivatives were effectively prepared via Ullmann-type reaction in a one-pot synthetic design. Six new s-triazine derivatives with potential biological activity were prepared and characterized.

Citovat

HAVRÁNKOVÁ, Eva; Jozef CSÖLLEI a Pavel PAZDERA. New Approach for the One-Pot Synthesis of 1,3,5-Triazine Derivatives: Application of Cu(I) Supported on a Weakly Acidic Cation-Exchanger Resin in a Comparative Study. Molecules. Basel: MDPI, 2019, roč. 24, č. 19, s. 1-10. ISSN 1420-3049. Dostupné z: https://doi.org/10.3390/molecules24193586.

@article{1566136,
   author = {Havránková, Eva and Csöllei, Jozef and Pazdera, Pavel},
   article_location = {Basel},
   article_number = {19},
   doi = {https://doi.org/10.3390/molecules24193586},
   keywords = {1 3 5-triazine; supported Cu(I) catalyst; Ullmann reaction; one-pot synthesis},
   language = {eng},
   issn = {1420-3049},
   journal = {Molecules},
   title = {New Approach for the One-Pot Synthesis of 1,3,5-Triazine Derivatives: Application of Cu(I) Supported on a Weakly Acidic Cation-Exchanger Resin in a Comparative Study},
   url = {https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6804075/},
   volume = {24},
   year = {2019}
}

TY  - JOUR
ID  - 1566136
AU  - Havránková, Eva - Csöllei, Jozef - Pazdera, Pavel
PY  - 2019
TI  - New Approach for the One-Pot Synthesis of 1,3,5-Triazine Derivatives: Application of Cu(I) Supported on a Weakly Acidic Cation-Exchanger Resin in a Comparative Study
JF  - Molecules
VL  - 24
IS  - 19
SP  - 1-10
EP  - 1-10
PB  - MDPI
SN  - 14203049
KW  - 1 3 5-triazine
KW  - supported Cu(I) catalyst
KW  - Ullmann reaction
KW  - one-pot synthesis
UR  - https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6804075/
L2  - https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6804075/
N2  - An efficient and simple methodology for Ullmann Cu(I)-catalyzed synthesis of di- and trisubstituted 1,3,5-triazine derivatives from dichlorotriazinyl benzenesulfonamide and corresponding nucleophiles is reported. Cations Cu(I) supported on macroporous and weakly acidic, low-cost industrial resin of polyacrylate type were used as a catalyst. The reaction times and yields were compared with traditional synthetic methods for synthesis of substituted 1,3,5-triazine derivatives via nucleophilic substitution of chlorine atoms in dichlorotriazinyl benzenesulfonamide. It was found that Ullmann-type reactions provide significantly shortened reaction times and, in some cases, also higher yields. Finally, trisubstituted s-triazine derivatives were effectively prepared via Ullmann-type reaction in a one-pot synthetic design. Six new s-triazine derivatives with potential biological activity were prepared and characterized.
ER  -

HAVRÁNKOVÁ, Eva; Jozef CSÖLLEI a Pavel PAZDERA. New Approach for the One-Pot Synthesis of 1,3,5-Triazine Derivatives: Application of Cu(I) Supported on a Weakly Acidic Cation-Exchanger Resin in a Comparative Study. \textit{Molecules}. Basel: MDPI, 2019, roč.~24, č.~19, s.~1-10. ISSN~1420-3049. Dostupné z: https://doi.org/10.3390/molecules24193586.

Přehled o publikaci