Catalyzed Claisen-Schmidt reaction by protonated aluminate mesoporous silica nanomaterial focused on the (E)-chalcone synthesis as a biologically active compound

Mohammad Reza Sazegar, Shaya Mahmoudian, Ali Mahmoudi, Sugeng Triwahyono, Aishah Abdul Jalil, Rino R. Mukti, Kamarudin Nur Hidayatul Nazirah, Monir K. Ghoreishi

Research output: Contribution to journalArticle

6 Citations (Scopus)

Abstract

The mesoporous silica structure (MSN) was synthesized using the sol-gel method followed by aluminum grafting and protonation and was then denoted as HAlMSN (Si/Al = 18.9). N2 physisorption confirmed the mesoporous structure with a pore diameter of 3.38 nm. 27Al NMR showed the presence of framework and extra-framework aluminum structures, which led to the formation of strong Lewis and Brønsted acidic sites. HAlMSN catalyzed the synthesis of (E)-chalcones through the Claisen-Schmidt reaction. Chalcone derivatives have been applied as biologically active compounds with anti-cancer, anti-inflammatory and diuretic pharmacological activities. The products were obtained via reactions on the protonic acid sites of HAlMSN. The significant advantages of this reaction are high yield, easy work up, short reaction time and also compatibility with various organic solvents. The products were obtained in an excellent conversion of 97% at 298 K. The results show that the electron donating substituents exhibit higher conversion in comparison to electron withdrawing substituents. The stability of the catalyst was investigated by reusing it five times for (E)-chalcone production and there was only a slight decrease in its catalytic activity. The highest product of (E)-chalcone was observed with a 1:2 molar ratio of benzaldehyde/acetophenone. A comparative study in chalcone synthesis using the heterogeneous catalysts demonstrated that HAlMSN has a significantly high activity at low temperature.

Original languageEnglish
Pages (from-to)11023-11031
Number of pages9
JournalRSC Advances
Volume6
Issue number13
DOIs
Publication statusPublished - 2016
Externally publishedYes

Fingerprint

Chalcone
Nanostructured materials
Silicon Dioxide
Silica
Aluminum
Catalysts
Physisorption
Electrons
Protonation
Organic solvents
Sol-gel process
Catalyst activity
Nuclear magnetic resonance
Chalcones
Derivatives
Acids
Diuretics
Anti-Inflammatory Agents
Temperature

ASJC Scopus subject areas

  • Chemical Engineering(all)
  • Chemistry(all)

Cite this

Sazegar, M. R., Mahmoudian, S., Mahmoudi, A., Triwahyono, S., Jalil, A. A., Mukti, R. R., ... Ghoreishi, M. K. (2016). Catalyzed Claisen-Schmidt reaction by protonated aluminate mesoporous silica nanomaterial focused on the (E)-chalcone synthesis as a biologically active compound. RSC Advances, 6(13), 11023-11031. https://doi.org/10.1039/c5ra23435b

Catalyzed Claisen-Schmidt reaction by protonated aluminate mesoporous silica nanomaterial focused on the (E)-chalcone synthesis as a biologically active compound. / Sazegar, Mohammad Reza; Mahmoudian, Shaya; Mahmoudi, Ali; Triwahyono, Sugeng; Jalil, Aishah Abdul; Mukti, Rino R.; Nur Hidayatul Nazirah, Kamarudin; Ghoreishi, Monir K.

In: RSC Advances, Vol. 6, No. 13, 2016, p. 11023-11031.

Research output: Contribution to journalArticle

Sazegar, Mohammad Reza ; Mahmoudian, Shaya ; Mahmoudi, Ali ; Triwahyono, Sugeng ; Jalil, Aishah Abdul ; Mukti, Rino R. ; Nur Hidayatul Nazirah, Kamarudin ; Ghoreishi, Monir K. / Catalyzed Claisen-Schmidt reaction by protonated aluminate mesoporous silica nanomaterial focused on the (E)-chalcone synthesis as a biologically active compound. In: RSC Advances. 2016 ; Vol. 6, No. 13. pp. 11023-11031.
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