Pronounced Catalytic Effect of Micellar Solution of Surfactants for Regioselective Alkylation of 4,5-Di- and 3,4,5-Triphenylimidazoles-2-thione

N. Rezki; M. Ait Sidhoum; M. R. Aouad; H. Ilikti; T. Benabdallah

doi:10.3139/113.110089

Published by De Gruyter April 5, 2013

Pronounced Catalytic Effect of Micellar Solution of Surfactants for Regioselective Alkylation of 4,5-Di- and 3,4,5-Triphenylimidazoles-2-thione

Stark ausgeprägter katalytischer Effekt mizellarer Tensidlösungen bei der regioselektiven Alkylierung von 4,5-Di- und 3,4,5-Triphenylimidazol-2-thion

N. Rezki , M. Ait Sidhoum , M. R. Aouad , H. Ilikti and T. Benabdallah

From the journal Tenside Surfactants Detergents

https://doi.org/10.3139/113.110089

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Abstract

An environmentally benign aqueous alkylation protocol for the regioselective synthesis of thioalkylated imidazoles using cationic, anionic and neutral surfactants has been achieved. The efficiency of the coupling reaction depends strongly on the nature and the concentration of the surfactant. The highest yield (up to 94%) was obtained in the presence of an anionic surfactant, while neutral or cationic surfactants gave poorer results with no change in regioselectivity.

Kurzfassung

Es wurde eine umweltfreundliche wässrige Alkylierungsmethode zur regioselektiven Synthese von thioalkylierten Imidazolen mittels kationischen, anionischen und nicht ionischen Tensiden entwickelt. Die Effizienz der Kupplungsreaktion hängt stark von der Art und der Konzentration des Tensids ab. Die höchste Ausbeute (bis zu 94%) wurde in Anwesenheit eines anionischen Tensids erhalten. Neutrale und kationische Tenside lieferten ohne Änderung der Regioselektivität schlechtere Resultate.

Key words:: Thioimidazoles; regioselective alkylation; surfactants; water

Stichwörter:: Thioimidazole; regioselektive Alkylierung; Tenside; Wasser

^∗ N. Rezki, Department of Chemistry, Faculty of Science, University of Science and Technology, – Mohamed Boudiaf – USTO-MB, BP: 1505 ELM'NOUAR ORAN 31000, Algeria. E-Mail: aouadmaha@yahoo.fr

Dr. N. Rezki was born in 1974, she has received her bachelor's degree in chemistry engineering in 1998 from the University of Sciences and Technology Oran and her master's degree in organic chemistry in 2001 from Al Mustansiriyah University Baghdad. She was awarded her PhD in organic chemistry in 2006 from Alexandria University under the supervision of Professor E. S. H. El Ashry. She has published about 10 publications. She is currently an associate professor at the Faculty of Sciences, University of Sciences and Technology Oran, Algeria.

Mr. M. Ait Sidhoum was born in 1973, he has received his bachelor's degree in chemistry engineering in 2006 and his master's degree in organic chemistry in 2008 from the University of Sciences and Technology Oran, Algeria.

Dr. M. R. Aouad was born in 1975, he has received his bachelor's degree in chemistry engineering in 1998 from the University of Sciences and Technology Oran and his master's degree in organic chemistry in 2001 from Al Mustansiriyah University Baghdad. He was awarded his PhD in organic chemistry in 2006 from Alexandria University under the supervision of Professor E. S. H. El Ashry. He has published about 10 publications. He is currently an associate professor at the Faculty of Sciences, University of Sciences and Technology Oran, Algeria.

Dr. H. Ilikti was born in 1958, he has received his bachelor's degree in organic chemistry in 1984 and his master's degree in organic chemistry in 1992 from the University of Sciences and Technology Oran. He was awarded his PhD in organic chemistry in 2004 from the University of Sciences and Technology Oran. He has supervised more than 6 MSc and PhD students and published about 8 publications. He is currently a professor at the Faculty of Sciences, University of Sciences and Technology Oran, Algeria.

Dr. T. Benabdallah was born in 1957, he has received his bachelor's degree in organic chemistry in 1980 and his master's degree in organic chemistry in 1983 from the University of Es-Senia, Oran. He was awarded his PhD in 1988 in organic chemistry from the University of AIX-Marseille-II under the supervision of Professor R. Guglielmetti. He has supervised more than 12 MSc and PhD students and published about 23 publications. He is currently a professor at the Faculty of Sciences, University of Sciences and Technology Oran, Algeria.

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Received: 2010-01-24

Published Online: 2013-04-05

Published in Print: 2010-11-01

Pronounced Catalytic Effect of Micellar Solution of Surfactants for Regioselective Alkylation of 4,5-Di- and 3,4,5-Triphenylimidazoles-2-thione

Abstract

Kurzfassung

References

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