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

N'Ta Christelle Ambeu (1, 2) , Déliko Camille Dago (1, 2) , Wacothon Karime Coulibaly (3) , Yves-Alain Békro (2) , Janat Akhanovna Mamyrbékova-Békro (2) , Jean Pierre Bazureau (1)

1 ISCR - Institut des Sciences Chimiques de Rennes
2 LCBOSN - Laboratoire de Chimie Bioorganique et des Substances Naturelles
3 Université Péléforo Gon Coulibaly, UFR des Sciences Biologiques, Korhogo BP 1328, Côte d’Ivoire

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.

Mots clés: 5-arylidene rhodanine; holmberg reaction; koenevenagel condensation; microwave; N-boc carbamate; one-pot twosteps; solution phase; trifuoroacetate salt

Domaines: Chimie organique; Chimie thérapeutique

N'Ta Christelle Ambeu, Déliko Camille Dago, Wacothon Karime Coulibaly, Yves-Alain Békro, Janat Akhanovna Mamyrbékova-Békro, et al.. Microwave Assisted Prospective Synthesis of New 5-Arylidene Rhodanine Derivatives Bearing a 3-[4-(3-Aminopropyl) piperazin-1-yl] propyl Side Chain. Current microwave chemistry, 2016, 3 (2), pp.145-156. ⟨10.2174/2213335602666150825215730⟩. ⟨hal-01452333⟩