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

Author(s): Christelle N'ta Ambeu, Camille Déliko Dago, Wacothon Karime Coulibaly, Yves-Alain Békro, Janat A. Mamyrbékova-Békro, Jean Pierre Bazureau.

Journal Name: Current Microwave Chemistry

Volume 3 , Issue 2 , 2016

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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.

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Article Details

Year: 2016
Page: [145 - 156]
Pages: 12
DOI: 10.2174/2213335602666150825215730
Price: $58

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