Thiazolidinones: novel insights from microwave synthesis, computational studies, and potentially bioactive hybrids

• Luan A. Martinho,
• Victor H. J. G. Praciano,
• Guilherme D. R. Matos,
• Claudia C. Gatto and
• Carlos Kleber Z. Andrade

Beilstein J. Org. Chem. 2025, 21, 2618–2636, doi:10.3762/bjoc.21.203

• different products were obtained), delivers excellent yields (up to 99%), and requires low catalyst loading (10 mol %). This new approach was successfully applied to the synthesis of eight novel imidazo[1,2-a]pyridine–thiazolidinone hybrids in good to excellent yields (66–99%). A spectroscopic study of

• (intramolecular charge transfer) process. Keywords: fluorescence; hybridization; imidazo[1,2-a]pyridines; Knoevenagel reaction; thiazolidinone; Introduction Heterocycles are compounds of significant interest to organic chemists as drug candidates due to their already widespread presence in many commercially

• scaffolds for several synthetic or natural compounds [5]. Five-membered heterocycles include the thiazolidinone nucleus, characterized by two heteroatoms and a carbonyl group on the fourth carbon, as seen in compounds like rhodanine and thiazolidine-2,4-dione derivatives (Figure 1). These privileged

Asymmetric synthesis of a stereopentade fragment toward latrunculins

• Benjamin Joyeux,
• Antoine Gamet,
• Nicolas Casaretto and
• Bastien Nay

Beilstein J. Org. Chem. 2023, 19, 428–433, doi:10.3762/bjoc.19.32

• partner (8) for the aldol reaction brings the thiazolidinone heterocycle of the natural product. It was synthesized in four steps from ʟ-cysteine ester derivative 16, first reacting with carbonyldiimidazole (CDI) to afford thiazolidinone 17 in 85% yield (Scheme 2). The nitrogen atom was protected with a

• PMB group in 72% yield (18), after deprotonation with NaH and reaction with PMBBr. The ester moiety of 18 was then chemoselectively reduced into alcohol 19 in 90% yield, in presence of LiBH4 to avoid the reduction of the thiazolidinone part. Finally, the aldehyde (8) was generated in 78% yield by

• thiazolidinone ring, possibly leading to a strong conformational distortion of Mosher's model. The question of the resulting stereoselectivity was thus left open for later resolution. To complete this study, the 1,3-anti-diastereoselective reduction of β-hydroxyketone 21 was undertaken through the Evans

KOt-Bu-promoted selective ring-opening N-alkylation of 2-oxazolines to access 2-aminoethyl acetates and N-substituted thiazolidinones

• Qiao Lin,
• Shiling Zhang and
• Bin Li

Beilstein J. Org. Chem. 2020, 16, 492–501, doi:10.3762/bjoc.16.44

• has not been reported. Thiazolidinone derivatives are important moieties in functional materials and natural products [12][13][14], such as latrunculin that has been obtained from the sponge Cacospongia mycofijiensis [15]. Convenient syntheses of thiazolidinone derivatives are highly attractive to

• synthetic chemists. However, only a few examples are reported for the synthesis of N-substituted thiazolidinones although the synthetic method of thiazolidinone was described in 1993 [16]. Frost and co-workers explored an efficient ruthenium-catalyzed O-to-S-alkyl migration of N-alkyloxazolidine-2-thiones

• to synthesize thiazolidinone derivatives through a Barton–McCombie pathway in 2015 [17] (Scheme 1b). Recently, potassium tert-butoxide has been shown to be an efficient promoter for C–C-bond formation reactions [18][19][20][21][22]. However, only few reports described C–N-bond cross-coupling

An effective one-pot access to polynuclear dispiroheterocyclic structures comprising pyrrolidinyloxindole and imidazothiazolotriazine moieties via a 1,3-dipolar cycloaddition strategy

• Alexei N. Izmest’ev,
• Galina A. Gazieva,
• Natalya V. Sigay,
• Sergei A. Serkov,
• Valentina A. Karnoukhova,
• Vadim V. Kachala,
• Alexander S. Shashkov,
• Igor E. Zanin,
• Angelina N. Kravchenko and
• Nina N. Makhova

Beilstein J. Org. Chem. 2016, 12, 2240–2249, doi:10.3762/bjoc.12.216

• of these two bands, one broad band is observed), and 1649–1634 cm−1 that are characteristic of oxindole, imidazolidinone, and thiazolidinone ring carbonyl groups. The 1H NMR spectra of compounds 4 exhibited, along with the proton signals of the imidazothiazolotriazine and oxindole moieties, the

Chemistry of polyhalogenated nitrobutadienes, 14: Efficient synthesis of functionalized (Z)-2-allylidenethiazolidin-4-ones

• Viktor A. Zapol’skii,
• Jan C. Namyslo,
• Mimoza Gjikaj and
• Dieter E. Kaufmann

Beilstein J. Org. Chem. 2014, 10, 1638–1644, doi:10.3762/bjoc.10.170

• focus on their anticancer [29][30][31] and anti-HIV potential [30][32]. Several 4-thiazolidinone derivatives such as ralitoline (anticonvulsant), etozoline (antihypertensive), pioglitazone (hypoglycemic) and thiazolidomycin (activity against streptomyces species) are already in the market [33]. Beyond

• of thiazolidinone chemistry including classical synthetic strategies has been reviewed comprehensively [18][19][20][21][22][23][24][25][26][27][28][36][37][38][39]. Even though among possible synthetic pathways the use of mercaptoacetic acid and its derivatives is well-established [40][41][42][43][44

• thiazolidinones 7–18, as an example the 4-iodophenyl substituted thiazolidinone 11 was subjected to X-ray analysis (see Supporting Information File 1). This confirmed the Z-configuration of the inner double bond which bears the sulfur atom of the hetero ring as well as the nitro group. The structural plot also

A facile, rapid, one-pot regio/stereoselective synthesis of 2-iminothiazolidin-4-ones under solvent/scavenger-free conditions

• Murugan Sathishkumar,
• Sangaraiah Nagarajan,
• Poovan Shanmugavelan,
• Murugan Dinesh and
• Alagusundaram Ponnuswamy

Beilstein J. Org. Chem. 2013, 9, 689–697, doi:10.3762/bjoc.9.78

• expected thiourea. Having established the new protocol for the synthesis of 2-iminothiazolidin-4-ones, the method was extended to the rapid synthesis of a library of thiazolidinone derivatives (Table 4). Further, it is pertinent to mention here the interesting regio/stereoselectivity noted in the synthesis

• thiazolidinone derivatives. Supporting Information Supporting Information File 112: Experimental procedures and product characterization for compounds (4a–j). Acknowledgements The author MS thanks UGC, New Delhi for the award of a junior research fellowship and the Department of Science and Technology, New

DBFOX- Ph/metal complexes: Evaluation as catalysts for enantioselective fluorination of 3-(2-arylacetyl)-2-thiazolidinones

• Takehisa Ishimaru,
• Norio Shibata,
• Dhande Sudhakar Reddy,
• Takao Horikawa,
• Shuichi Nakamura and
• Takeshi Toru

Beilstein J. Org. Chem. 2008, 4, No. 16, doi:10.3762/bjoc.4.16

• Fluorination of 1 to 2. Optimisation of the Conditions for DBFOX-Ph/Ni(II)-Catalysed Enantioselective Fluorination of 3-(2-Phenylacetyl)-2-thiazolidinone (1a)a. Enantioselective Fluorination Reaction of 3-(2-Arylacetyl)-2-thiazolidinones with NFSI Catalyzed by DBFOX-Ph/Ni(II)a. Supporting Information

New acylides: synthesis of 3-O-[γ-(4-oxo-2-aryl- thiazolidin- 3-yl)butyryl]erythromycin A derivatives

• Deepa Pandey,
• Wahajul Haq and
• Seturam B. Katti

Beilstein J. Org. Chem. 2008, 4, No. 14, doi:10.3762/bjoc.4.14

• -thiazolidin-3-yl)butyryl]erythromycin A derivatives have been synthesized. The 3-hydroxy group was derivatised to a primary amine and subsequently the thiazolidinone nucleus was generated at the amino functionality through DCC mediated one-pot three-component reaction in good yields. Background Second

• 3-O-acyl derivatives with nitrogen heterocyclic moieties, namely pyridylacetyl, were mostly active [9]. This encouraged us to explore the synthesis of 3-O-acylides bearing other heterocyclic systems for example thiazolidinone in place of the pyridyl residue. The thiazolidinone functionality in the

• -methylerythromycin A (1) was generated using the method available in the literature [13]. We have developed a synthesis where the 3-OH group of 1 was functionalized to an amino group using the γ-aminobutyryl spacer and subsequently a variety of thiazolidinone moieties were generated at the amino group. We have