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Issue 7, 2018
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Palladium functionalized phosphinite polyethyleneimine grafted magnetic silica nanoparticles as an efficient catalyst for the synthesis of isoquinolino[1,2-b]quinazolin-8-ones

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Abstract

In this paper, a novel methodology is introduced for the synthesis of novel 5-methyl-8H-isoquinolino[1,2-b]quinazolin-8-one derivatives based on an efficient immobilized palladium catalyzed intramolecular carbon–carbon bond formation. The novel catalyst is fabricated by immobilization of Pd on phosphinite polyethyleneimine functionalized Fe3O4@SiO2 core–shell nanoparticles (denoted as Pd@OPPh2–PEI–mSiO2 NPs). In this catalyst, PEI moieties act as both a water dispersant and base in the reaction. In the key step, 3-allyl-2-(2-bromophenyl)-2,3-dihydroquinazolin-4(1H)-ones (3a–i) were synthesized via a cyclization reaction between N-allyl-2-aminobenzamides and 2-bromobenzaldehyde. The latter obtained materials then underwent an intramolecular carbon–carbon bond formation in the presence of the Pd@Ph2PO–PEI–mSiO2 catalyst to give 5-methyl-13,13a-dihydro-8H-isoquinolino[1,2-b]quinazolin-8-ones (4a–i).

Graphical abstract: Palladium functionalized phosphinite polyethyleneimine grafted magnetic silica nanoparticles as an efficient catalyst for the synthesis of isoquinolino[1,2-b]quinazolin-8-ones

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Publication details

The article was received on 07 Dec 2017, accepted on 22 Feb 2018 and first published on 23 Feb 2018


Article type: Paper
DOI: 10.1039/C7NJ04837H
Citation: New J. Chem., 2018,42, 5499-5507
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    Palladium functionalized phosphinite polyethyleneimine grafted magnetic silica nanoparticles as an efficient catalyst for the synthesis of isoquinolino[1,2-b]quinazolin-8-ones

    S. Bahadorikhalili, M. Mahdavi, L. Ma’mani, A. Shafiee, H. Mahdavi and T. Akbarzadeh, New J. Chem., 2018, 42, 5499
    DOI: 10.1039/C7NJ04837H

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