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Microwave Assisted Prospective Synthesis of New 5-Arylidene Rhodanine Derivatives Bearing a 3-[4-(3-Aminopropyl)piperazin-1-yl]propyl Side Chain

[ Vol. 3 , Issue. 2 ]

Author(s):

Christelle N'ta Ambeu, Camille Déliko Dago, Wacothon Karime Coulibaly, Yves-Alain Békro, Janat A. Mamyrbékova-Békro and Jean Pierre Bazureau   Pages 145 - 156 ( 12 )

Abstract:


A series of (5Z) 5-arylidene 2-thioxo-1,3-thiazolidin-4-one derivatives 7(a-l) bearing a [4-(3-aminopropyl)piperazin-1-yl]propyl side chain in N-3 position was prepared using a solution phase protocol assisted by microwave dielectric heating. These new compounds were synthesized in four steps with overall yields ranging from 12 to 33% via a "one-pot two-steps" protocol based on Holmberg reaction followed by a stereocontrolled Knoevenagel condensation. The rhodanine intermediate 4' issued from Holmberg reaction under microwave was also isolated and identified by spectroscopic methods of analysis. The twelve deprotected products 7(a-l) have been obtained with a Z-geometry about their exocyclic double bond. All N-Boc intermediates 6(a-l) and deprotected rhodanine derivatives 7(a-l) issued from trifluoroacetic acid treatment have been characterized by 1H, 13C and HRMS.

Keywords:

5-arylidene rhodanine, holmberg reaction, koenevenagel condensation, microwave, N-boc carbamate, one-pot twosteps, solution phase, trifuoroacetate salt.

Affiliation:

Université de Rennes 1, Institut des Sciences Chimiques de Rennes, ISCR UMR CNRS 6226, groupe Ingéniérie Chimique et Molécules pour le Vivant (ICMV), Campus de Beaulieu, Bât. 10A, 263 Avenue du Général Leclerc, CS 74205, 35042 Rennes Cedex, France.



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