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.
Current Microwave Chemistry
Title:Microwave Assisted Prospective Synthesis of New 5-Arylidene Rhodanine Derivatives Bearing a 3-[4-(3-Aminopropyl)piperazin-1-yl]propyl Side Chain
Volume: 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
Affiliation:
Keywords: 5-arylidene rhodanine, holmberg reaction, koenevenagel condensation, microwave, N-boc carbamate, one-pot twosteps, solution phase, trifuoroacetate salt.
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.
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N'ta Ambeu Christelle, Dago Déliko Camille, Coulibaly Karime Wacothon, Békro Yves-Alain, Mamyrbékova-Békro A. Janat and Bazureau Pierre Jean, 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) . https://dx.doi.org/10.2174/2213335602666150825215730
DOI https://dx.doi.org/10.2174/2213335602666150825215730 |
Print ISSN 2213-3356 |
Publisher Name Bentham Science Publisher |
Online ISSN 2213-3364 |
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