An efficient method for Knoevenagel condensation: a facile synthesis of 5-arylidenyl 2,4-thiazolidinedione

Abstract

Knoevenagel condensation of various aromatic aldehydes with 2,4-thiazolidinedione has been carried out in polyethylene glycol-300. The reactions were carried out at moderate temperature with very simple isolation procedure and with better yields.

Design, Synthesis and Characterization of Some Novel 3-Coumarinyl- 5-aryliden-1,3-thiazolidine-2,4-diones and Their Antioxidant Activity

“…sulfuric acid at −10 • C, according to the literature method [18] (Scheme 1). 1,3-thiazolidine-2,4-dione (2) was obtained from monochloroacetic acid and thiourea in hot water [7], and yielded up on Knoevenagel condensation [19] with substituted aromatic aldehydes the 5-arylmethylidene-1,3-thiazolidine-2,4-diones 3a -r (Scheme 2). A series of novel 3,5-disubstituted 1,3-thiazolidin-2,4-diones 5a -r was obtained by condensation of compounds 3a -r with 1 (Scheme 3).…”

Alum catalyzed simple and efficient synthesis of 5-arylidene-2,4-thiazolidinedione in aqueous media

“…piperidine in EtOH (6), AlPO 4 ÁZeolite in EtOH:H 2 O (7), and polyethylene glycol (8). However, above reported methods suffered from one or more drawbacks such as prolonged reaction times (6) with frequently low yields (8). Therefore, the development of a simple, efficient, and versatile method is still strongly desirable.…”

“…It is wellknown that 5-arylidene-2,4-thiazolidinediones are generally synthesized by condensation of aromatic aldehydes with 2,4-thiazolidinedione in organic solvents, i.e. piperidine in EtOH (6), AlPO 4 ÁZeolite in EtOH:H 2 O (7), and polyethylene glycol (8). However, above reported methods suffered from one or more drawbacks such as prolonged reaction times (6) with frequently low yields (8).…”

Sonochemistry to promote the synthesis of 5- arilydenethiazolidine-2,4-diones

“…1 For this aldol condensation, the literature reports several methods such as: KOH or piperidine in reflux of ethanol or toluene, 2 polyethene glycol (PEG-300) in reflux without base 3 . These conditions take some hours of reaction.…”