Original scientific paper

https://doi.org/10.5562/cca1983

Highly Efficient One-pot Synthesis, Antimicrobial and Docking Studies of Newer β-amino Carbonyl Derivatives Catalyzed by Silica Sulfuric Acid

Kh. A. M. El-Bayouki ; Organometallic and Organometalloid Chemistry Dept., National Research Centre, Dokki, Cairo, Egypt
W. M. Basyouni ; Organometallic and Organometalloid Chemistry Dept., National Research Centre, Dokki, Cairo, Egypt
A. S. El-Sayed ; Chemistry Dept. Faculty of Science, Al-Azhar University, Cairo, Egypt
W. M. Tohamy ; Organometallic and Organometalloid Chemistry Dept., National Research Centre, Dokki, Cairo, Egypt
A. A. El-Henawy ; Chemistry Dept. Faculty of Science, Al-Azhar University, Cairo, Egypt

Abstract

Mannich reaction was applied between 4-fluorobezaldehyde, selected acetophenone and several anilines, catalyzed by silica sulfuric acid for the synthesis of β-amino carbonyl derivatives. Reaction time and yield of the products depended on the nature of acetophenone and aniline subsituents. Using aliphatic amines instead of aromatic amines under same reaction conditions, afforded aldol condensation products without yielding the expected β-amino ketones. Replacing the acetophenone derivatives with rhodanine yielded 5-(4-fluorobenzylidene)-thioxothiazolidin-4-one. Using 2-aminothiophenol instead of the aniline derivatives, 2-(4-fluorophenyl)benzothiazole was obtained without isolation of the expected (mercapto-phenylamino)-1-(4-substitutedphenyl)propan-1-ones. A proposed reaction mechanism was suggested. Docking studies were designed to gain clear picture of the high active compound(s). A model of high active molecules was mapped for the antimicrobial screening and compared with least active compound(s). (doi: 10.5562/cca1983)

Keywords

multi-component reaction; Mannich reactions; β-aminoketones; silica sulfuric acid; docking studies

Hrčak ID:

91856

URI

https://hrcak.srce.hr/91856

Publication date:

31.10.2012.

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