African Journal of
Pure and Applied Chemistry

  • Abbreviation: Afr. J. Pure Appl. Chem.
  • Language: English
  • ISSN: 1996-0840
  • DOI: 10.5897/AJPAC
  • Start Year: 2007
  • Published Articles: 336

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

Abstract

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.