Improved Preparation of 2,4-Thiazolidinedione

Meng, Guangrong; Gao, Yang; Zheng, Meilin

doi:10.1080/00304948.2011.582008

Cited by 12 publications

(6 citation statements)

References 5 publications

(2 reference statements)

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“…The 2-iminothiazolidine-4-one HCl salt was isolated and then neutralized with sodium hydroxide to give 2-iminothiazolidine-4-one as free base, which was hydrolyzed under concentrated hydrochloride condition to give 5. This early method was improved via a one-pot procedure (84 %) [19] or a green synthesis method by our group recently (79 %) [20]. Subsequent research on this cyclization reaction indicated that the yield of both the one-pot and green methods could be enhanced by adjusting the amount and concentration of solvent.…”

Section: Resultsmentioning

confidence: 96%

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Synthetic optimization of rosiglitazone and related intermediates for industrial purposes

et al. 2015

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As an important newly Food and Drug Administration (FDA)-approved drug for treating diabetes, rosiglitazone (1) has received much attention from researchers in many areas. To search for an economical and convenient synthesis method for 1, we explored the reaction conditions and workup of a scalable five-step synthetic route by an orthogonal method to determine the best condition for each reaction step. The starting materials are commercially available, including 2-chloropyridine (2), N-methylethanolamine (3), 4-fluorobenzaldehyde (4a) or 4-hydroxybenzaldehyde (4b), and 1,3-thiazolidine-2,4-dione (5). The five sequential reaction steps are cyclization, alkylation, etherification, condensation, and reduction, having optimal yield of 90, 99, 59, 75, and 91 %, respectively. The best overall yield to synthesize rosiglitazone based on compound 2 was 40 %, being suitable for industrial purposes, using water as a green solvent and avoiding column chromatography during the last three reaction steps.

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Section: Resultsmentioning

confidence: 96%

“…Knoevenagel condensation between aldehyde 7 and 5 provides the intermediate 8. (5) was synthesized directly from 2-chloroacetic acid (9) and thiourea (10) via cyclization in either hydrochloride or water using our previously improved methods [19,20]. The optimal overall yield of this linear synthesis route for 1 was 40 % (Scheme 2).…”

Section: Introductionmentioning

confidence: 99%

Synthetic optimization of rosiglitazone and related intermediates for industrial purposes

et al. 2015

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“…While changing the concentration of HCl slightly affects the yield, the volume of water has an extensive effect on the yield of thiazolidinedione where a larger amount of water added leads to heavy loss and lower yield [66] . The reaction also can be done in the absence of hydrochloric acid, giving acceptable yield [67] …”

Section: Synthesis Of 24‐thiazolidinedione Ringmentioning

confidence: 99%

Chemistry and Applications of Functionalized 2,4‐Thiazolidinediones

et al. 2023

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Thiazolidinedione (TZD) is one of the privileged heterocyclic rings and has shown many biological applications in medicinal chemistry and drug discovery. This review covers the synthetic approaches of TZD and its derivatives, different synthetic techniques for affording the desired regioselectivity and stereoselectivity, and the techniques that would enhance reaction conditions such as microwave, one‐pot, or ultrasound synthesis. It focuses on synthetic challenges of glitazones and the transformation of other heterocycles to TZD. Moreover, the chemical and biological behavior of TZD through the substitution in the N3 position, modification of the C5 position, annealing in complex heterocyclic systems, and hybridization with other pharmacologically attractive moieties are discussed. All reactions mentioned are provided as possible with different reaction conditions, mechanisms, derivatives scope, yield and clarified by applications of such reactions in the construction of potential medicinal agents. The review also answers questions about rapid racemization of glitazones, their toxicity, considering TZD as pan‐assay interference compounds (PAINS) or not, and the influence of saturation of 5‐position of TZD in their biological activities. This review is a comprehensive guide to make informed decisions for construction of TZD derivatives with biological potentials.

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“…It should be noted that conducting the reaction utilising HCl as the acid and heating for a 7–8 hour period provided the highest yield of 3 at 94 % (Figure 3). [11,12] …”

Section: Introduction To Tzdmentioning

confidence: 99%

Thiazolidinediones: An In–Depth Study of Their Synthesis and Application to Medicinal Chemistry in the Treatment of Diabetes Mellitus

2021

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2,4‐Thiazolidinedione (TZD) is a privileged and highly utilised scaffold for the development of pharmaceutically active compounds. This sulfur‐containing heterocycle is a versatile pharmacophore that confers a diverse range of pharmacological activities. TZD has been shown to exhibit biological action towards a vast range of targets interesting to medicinal chemists. In this review, we attempt to provide insight into both the historical conventional and the use of novel methodologies to synthesise the TZD core framework. Further to this, synthetic procedures utilised to substitute the TZD molecule at the activated methylene C5 and N3 position are reviewed. Finally, research into developing clinical agents, which act as modulators of peroxisome proliferator‐activated receptors gamma (PPARγ), protein tyrosine phosphatase 1B (PTP1B) and aldose reductase 2 (ALR2), are discussed. These are the three most targeted receptors for the treatment of diabetes mellitus (DM).

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Improved Preparation of 2,4-Thiazolidinedione

Cited by 12 publications

References 5 publications

Synthetic optimization of rosiglitazone and related intermediates for industrial purposes

Synthetic optimization of rosiglitazone and related intermediates for industrial purposes

Chemistry and Applications of Functionalized 2,4‐Thiazolidinediones

Thiazolidinediones: An In–Depth Study of Their Synthesis and Application to Medicinal Chemistry in the Treatment of Diabetes Mellitus

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