An Efficient Synthesis of Pyridoxal Oxime Derivatives under Microwave Irradiation

An Efficient Synthesis of Pyridoxal Oxime Derivatives under Microwave Irradiation

Quaternary salts of pyridoxal oxime have been synthesized by the quaternization of pyridoxal oxime with substituted phenacyl bromides using microwave heating. Microwave-assisted rapid synthesis was done both in solvent (acetone) and under solvent-free conditions. Good to excellent yields (58%–94%)...

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Main Authors: Dajana Gašo-Sokač, Valentina Bušić, Mario Cetina, Marijana Jukić
Format: Article
Language:English
Published: MDPI AG 2014-06-01
Series:Molecules
Subjects:
eco-friendly quaternization
microwave synthesis
phenacyl bromides
pyridoxal oxime
Online Access:http://www.mdpi.com/1420-3049/19/6/7610
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spelling doaj-9c997dcc0e6d442c87dc831225d7a4812020-11-24T23:02:33ZengMDPI AGMolecules1420-30492014-06-011967610762010.3390/molecules19067610molecules19067610An Efficient Synthesis of Pyridoxal Oxime Derivatives under Microwave IrradiationDajana Gašo-Sokač0Valentina Bušić1Mario Cetina2Marijana Jukić3Josip Juraj Strossmayer University of Osijek, Faculty of Food Technology Osijek, Kuhačeva 20, 31000 Osijek, CroatiaJosip Juraj Strossmayer University of Osijek, Faculty of Food Technology Osijek, Kuhačeva 20, 31000 Osijek, CroatiaUniversity of Zagreb, Faculty of Textile Technology, Department of Applied Chemistry, Prilaz baruna Filipovića 28a, 10000 Zagreb, CroatiaFaculty of Food Technology and Biotechnology, Department of Chemistry and Biochemistry, Pierottijeva 6, 10000 Zagreb, CroatiaQuaternary salts of pyridoxal oxime have been synthesized by the quaternization of pyridoxal oxime with substituted phenacyl bromides using microwave heating. Microwave-assisted rapid synthesis was done both in solvent (acetone) and under solvent-free conditions. Good to excellent yields (58%–94%) were obtained in acetone in very short reaction times (3–5 min) as well as in the solvent-free procedure (42%–78%) in very short reaction times (7–10 min) too. Effective metodologies for the preparation of pyridoxal oxime quaternary salts, having the advantagies of being eco-friendly, easy to handle, and performed in shorter reactions time are presented. The structure of compound 7, in which a 4-fluorophenacyl moiety is bonded to the pyridinium ring nitrogen atom, was unequivocally confirmed by the single-crystal X-ray diffraction method.http://www.mdpi.com/1420-3049/19/6/7610eco-friendly quaternizationmicrowave synthesisphenacyl bromidespyridoxal oxime
collection DOAJ
language English
format Article
sources DOAJ
author Dajana Gašo-Sokač
Valentina Bušić
Mario Cetina
Marijana Jukić
spellingShingle Dajana Gašo-Sokač
Valentina Bušić
Mario Cetina
Marijana Jukić
An Efficient Synthesis of Pyridoxal Oxime Derivatives under Microwave Irradiation
Molecules
eco-friendly quaternization
microwave synthesis
phenacyl bromides
pyridoxal oxime
author_facet Dajana Gašo-Sokač
Valentina Bušić
Mario Cetina
Marijana Jukić
author_sort Dajana Gašo-Sokač
title An Efficient Synthesis of Pyridoxal Oxime Derivatives under Microwave Irradiation
title_short An Efficient Synthesis of Pyridoxal Oxime Derivatives under Microwave Irradiation
title_full An Efficient Synthesis of Pyridoxal Oxime Derivatives under Microwave Irradiation
title_fullStr An Efficient Synthesis of Pyridoxal Oxime Derivatives under Microwave Irradiation
title_full_unstemmed An Efficient Synthesis of Pyridoxal Oxime Derivatives under Microwave Irradiation
title_sort efficient synthesis of pyridoxal oxime derivatives under microwave irradiation
publisher MDPI AG
series Molecules
issn 1420-3049
publishDate 2014-06-01
description Quaternary salts of pyridoxal oxime have been synthesized by the quaternization of pyridoxal oxime with substituted phenacyl bromides using microwave heating. Microwave-assisted rapid synthesis was done both in solvent (acetone) and under solvent-free conditions. Good to excellent yields (58%–94%) were obtained in acetone in very short reaction times (3–5 min) as well as in the solvent-free procedure (42%–78%) in very short reaction times (7–10 min) too. Effective metodologies for the preparation of pyridoxal oxime quaternary salts, having the advantagies of being eco-friendly, easy to handle, and performed in shorter reactions time are presented. The structure of compound 7, in which a 4-fluorophenacyl moiety is bonded to the pyridinium ring nitrogen atom, was unequivocally confirmed by the single-crystal X-ray diffraction method.
topic eco-friendly quaternization
microwave synthesis
phenacyl bromides
pyridoxal oxime
url http://www.mdpi.com/1420-3049/19/6/7610
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