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 and Pavel PAZDERA

Basic information

Original name

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

Authors

HAVRÁNKOVÁ, Eva (203 Czech Republic, belonging to the institution), Jozef CSÖLLEI (203 Czech Republic, belonging to the institution) and Pavel PAZDERA (203 Czech Republic, guarantor, belonging to the institution)

Edition

Molecules, Basel, MDPI, 2019, 1420-3049

Other information

Language

English

Type of outcome

Článek v odborném periodiku

Field of Study

10401 Organic chemistry

Country of publisher

Switzerland

Confidentiality degree

není předmětem státního či obchodního tajemství

References:

Full Text

Impact factor

Impact factor: 3.267

RIV identification code

RIV/00216224:14310/19:00110875

Organization unit

Faculty of Science

DOI

http://dx.doi.org/10.3390/molecules24193586

UT WoS

000496242300171

Keywords in English

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

Abstract

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 and 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, vol. 24, No 19, p. 1-10. ISSN 1420-3049. Available from: https://dx.doi.org/10.3390/molecules24193586.

@article{1566136,
   author = {Havránková, Eva and Csöllei, Jozef and Pazdera, Pavel},
   article_location = {Basel},
   article_number = {19},
   doi = {http://dx.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 and 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, vol.~24, No~19, p.~1-10. ISSN~1420-3049. Available from: https://dx.doi.org/10.3390/molecules24193586.

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