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Microwave Assisted Synthesis of a Small Library of Substituted N,N′-Bis((8-hydroxy-7-quinolinyl)methyl)-1,10-diaza-18-crown-6 Ethers

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Università di Bologna, Dipartimento di Biochimica “G. Moruzzi”, Bologna, Italy
Università di Bologna, Dipartimento di Medicina Interna, dell’Invecchiamento e Malattie Nefrologiche, Bologna, Italy
Università di Bologna, Dipartimento di Chimica “G. Ciamician”, Bologna, Italy
§Stefano Iotti is a member of the National Institute of Biostructures and Biosystems.
Cite this: J. Org. Chem. 2010, 75, 18, 6275–6278
Publication Date (Web):August 17, 2010
https://doi.org/10.1021/jo101173t
Copyright © 2010 American Chemical Society

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    Abstract

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    N,N′-Bis-((8-hydroxy-7-quinolinyl)methyl)-1,10-diaza-18-crown-6 ether 1a and its analogue 1c are known as fluorescent sensors of magnesium in living cells. With the aim to investigate the effects of the substitution pattern on the photophysical properties of ligands 1 and their metal complexes, we developed an efficient microwaves enhanced one-pot Mannich reaction to double-armed diaza-crown ligands 1 carrying a variety of substituents. This new protocol is characterized by shorter reaction times, enhanced yields, and improved product purities with respect to the use of conventional conductive heating.

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    Characterization data, experimental details, and copies of 1H and 13C NMR spectra of compounds synthesized. This material is available free of charge via the Internet at http://pubs.acs.org.

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