African Journal of Pure and Applied Chemistry
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Article Number - 4083C7C46886


Vol.8(8), pp. 110-115 August, 2014 , August 2014
DOI: 10.5897/AJPAC2014.0575
ISSN: 1996-0840



Full Length Research Paper

Solvent effect and catalysis in the synthesis of thiosemicarbazone derivatives from ketones and 4’-phenylthiosemicarbazide



Urbain C. Kasséhin
  • Urbain C. Kasséhin
  • Medicinal Chemistry, Louvain Drug Research Institute, Université catholique de Louvain. 73, Bte B1.73.10, Av. E. Mounier B-1200 Bruxelles, Belgique.U.E. Belgium.
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Fernand A. Gbaguidi
  • Fernand A. Gbaguidi
  • Laboratoire de Chimie Pharmaceutique Organique, Ecole de Pharmacie, Faculté des Sciences de la Santé, Université d'Abomey-Calavi, Campus du Champ de Foire, 01 BP 188, Cotonou Benin Republic West Africa.
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Coco N. Kapanda
  • Coco N. Kapanda
  • Medicinal Chemistry, Louvain Drug Research Institute, Université catholique de Louvain. 73, Bte B1.73.10, Av. E. Mounier B-1200 Bruxelles, Belgique.U.E. Belgium
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Christopher R. McCurdy
  • Christopher R. McCurdy
  • Medicinal Chemistry, School of Pharmacy, 419 Faser Hall, P. O. BOX 1848, Oxford, University, Mississipi 386771848, United States.
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Jacques H. Poupaert
  • Jacques H. Poupaert
  • Medicinal Chemistry, Louvain Drug Research Institute, Université catholique de Louvain. 73, Bte B1.73.10, Av. E. Mounier B-1200 Bruxelles, Belgique.U.E. Belgium.
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 Received: 13 May 2014  Accepted: 12 August 2014  Published: 31 August 2014

Copyright © 2014 Author(s) retain the copyright of this article.
This article is published under the terms of the Creative Commons Attribution License 4.0


In this paper, we performed a series of experiments aiming at establishing the solvent effects in the condensation of 4-phenylthiosemicarbazide with 4-nitroacetophenone to form the expected thiosemicarbazone derivative, reaction  which  was chosen  as pilot reaction, having in mind to set up optimal reaction conditions for the future elaboration of a compound library of thiosemicarbazone derivatives. Methanol was found to be a suitable solvent for this purpose. As a general rule, acid catalysis was found to perform better than base catalysis. General acid-base catalysis performed also in a quite satisfactory manner and in this connection, among the catalytic systems, anilinium chloride performed optimally allowing the reaction to go to completion at room temperature in excellent yield within 24 h at room temperature.  A series of six bench mark molecules of increasing steric effect were synthesized in fair to good yields using this method.

 

Key words: Thiosemicarbazone, thiosemicarbazide, solvent effect, acid-base catalysis, alpha-effect, nucleophilic catalysis, anilinium catalysis.

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APA Kasséhin, U. C., Gbaguidi, F. A., Kapanda, C. N., McCurdy, C. R., & Poupaert, J. H. (2014). Solvent effect and catalysis in the synthesis of thiosemicarbazone derivatives from ketones and 4’-phenylthiosemicarbazide. African Journal of Pure and Applied Chemistry, 8(8), 110-115 August, 2014 .
Chicago Urbain C. Kass&ehin, , Fernand A. Gbaguidi, Coco N. Kapanda, Christopher R. McCurdy and Jacques H. Poupaert. "Solvent effect and catalysis in the synthesis of thiosemicarbazone derivatives from ketones and 4’-phenylthiosemicarbazide." African Journal of Pure and Applied Chemistry 8, no. 8 (2014): 110-115 August, 2014 .
MLA Urbain C. Kasseacute;hin, et al. "Solvent effect and catalysis in the synthesis of thiosemicarbazone derivatives from ketones and 4’-phenylthiosemicarbazide." African Journal of Pure and Applied Chemistry 8.8 (2014): 110-115 August, 2014 .
   
DOI 10.5897/AJPAC2014.0575
URL http://academicjournals.org/journal/AJPAC/article-abstract/4083C7C46886

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