Sulfonic acid functionalized boron nitride nano materials as a microwave-assisted efficient and highly biologically active one-pot synthesis of piperazinyl-quinolinyl fused Benzo[c]acridine derivatives

Boron nitride nano material based solid acid catalyst was found to be an efficient and reusable sulfonic acid catalyst for the synthesis of one-pot Knoevenagel and Michael type reactions in 3, 3-dimethyl-9-(2-(4-methylpiperazin-1-yl) quinolin-3-yl)-3, 4, 9, 10-tetrahydroacridin-1(2H)-one derivatives...

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Bibliographic Details
Published in:Materials chemistry and physics 2017-02, Vol.188, p.154-167
Main Authors: Murugesan, Arul, Gengan, R.M., Krishnan, Anand
Format: Article
Language:English
Subjects:
Boron
Boron nitride
Catalysts
Chemical synthesis
Deoxyribonucleic acid
DNA
Fourier transforms
Knoevenagel reactions
Microwave irradiation
Molecular docking
Raman spectroscopy
Reaction time
Solid acid catalyst
Sulfonic acid
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Summary:Boron nitride nano material based solid acid catalyst was found to be an efficient and reusable sulfonic acid catalyst for the synthesis of one-pot Knoevenagel and Michael type reactions in 3, 3-dimethyl-9-(2-(4-methylpiperazin-1-yl) quinolin-3-yl)-3, 4, 9, 10-tetrahydroacridin-1(2H)-one derivatives under microwave irradiation conditions. The catalyst was prepared by mixing boron nitrile and (3-mercaptopropyl) trimethoxysilane. This is simple and safe method for the preparation of solid acid catalysts. The morphological properties of catalyst determined by using FT-IR, XRD, TEM, SEM and Raman spectroscopy. The synthesised catalyst was employed in Knoevenagel and Michael type reactions to synthesise novel piperazinyl-quinolinyl based acridine derivatives. Furthermore the newly-synthesised compounds have been used for molecular docking in DNA binding studies. The method developed in this study has the advantages of good yield, simplicity coupled with safety and short reaction time. Most importantly it was found that the solid acid catalyst can be recycled with only 5% loss of activity. [Display omitted] •One-pot Synthesis of Knoevenagel and Michel type reactions.•Synthesis of Sulfonic acid Functionalized Boron nitride nano materials.•Synthesis of piperazinyl-quinolinyl fused Benzo[c]acridine derivatives under Microwave irradiation.•Molecular docking studies were performed on piperazinyl-quinolinyl acridine derivatives using DNA.
ISSN:0254-0584
1879-3312
DOI:10.1016/j.matchemphys.2016.12.039