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Issue 63, 2020, Issue in Progress

Effective methods for the synthesis of hydrazones, quinazolines, and Schiff bases: reaction monitoring using a chemometric approach

Author affiliations

Abstract

Synthesis of hydrazones (1a–4a and 1b–4b), quinazolines (3c·MeOH and 3d·MeOH), and hydrazone-Schiff bases (4c and 4d) is achieved by combining suitable aldehydes (2,3- or 2,4-dihydroxybenzaldehyde) with four hydrazides (isonicotinic, nicotinic, and 2- or 4-aminobenzoic acid hydrazide). A suite of approaches for their preparation is described: solution-based synthesis, mechanosynthesis, and solid-state melt reactions. The mechanochemical approach is generally a better choice for the quinazolines, while the solid-state melt reaction is more efficient for derivatives of (iso)nicotinic based hydrazones. Crystalline amine-functionalised hydrazones 4a and 4b undergo post-synthetic modifications in reactions with 3- or 4-pyridinecarbaldehyde vapours to form hydrazone-Schiff bases 4a-3py, 4b-3py, 4a-4py, and 4b-4py. Mechanochemical and vapour-mediated reactions are followed by ex situ powder X-ray diffraction and IR-ATR methods, respectively. The chemometric analysis of these data using principal component analysis provided an insight into the reaction profiles and reaction times. Azines (5a and 5b), achieved from aldehydes and hydrazine, reversibly change colour in response to temperature changes. The structures of all products are ascertained by a combined use of spectroscopic and X-ray diffraction methods. The cytotoxic and antimicrobial activities of all compounds against selected human cancer cell lines and bacterial strains are evaluated.

Graphical abstract: Effective methods for the synthesis of hydrazones, quinazolines, and Schiff bases: reaction monitoring using a chemometric approach

Supplementary files

Article information


Submitted
08 Aug 2020
Accepted
04 Oct 2020
First published
20 Oct 2020

This article is Open Access

RSC Adv., 2020,10, 38566-38577
Article type
Paper

Effective methods for the synthesis of hydrazones, quinazolines, and Schiff bases: reaction monitoring using a chemometric approach

J. Pisk, I. Đilović, T. Hrenar, D. Cvijanović, G. Pavlović and V. Vrdoljak, RSC Adv., 2020, 10, 38566 DOI: 10.1039/D0RA06845D

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