Fe₃O₄@vitamin B₁ as a sustainable superparamagnetic heterogeneous nanocatalyst promoting green synthesis of trisubstituted 1,3‐thiazole derivatives

Abstract

Fe3O4@vitamin B1 was designed and prepared as an inexpensive and efficient heterogeneous nanocatalyst for the synthesis of new 1,3‐thiazol derivatives. The structure of the nanomagnetic catalyst was comprehensively characterized using Fourier transform infrared spectroscopy, scanning electron microscopy, transmission electron microscopy, energy‐dispersive X‐ray spectroscopy, vibrating sample magnetometry and thermogravimetric analysis. The three‐component, one‐pot condensation of arylglyoxal monohydrate, cyclic 1,3‐dicarbonyls and thioamides in water as a green solvent was applied for the preparation of 1,3‐thiazol derivatives. Simple preparation of the catalyst from commercially available materials, high catalytic activity, simple operation, short reaction times, high yields and use of green solvent are some advantages of this protocol. The superparamagnetic nanocatalyst is magnetically separable and retains its stability after recycling for at least five consecutive runs without detectable activity loss.

Emerging green synthetic routes for thiazole and its derivatives: Current perspectives

“…Shaterian and Molaei [87] S C H E M E 41 Fe 3 O 4 @SiO 2 @KIT-6 promoted synthesis of 2-hydrazonyl-4-phenyl thiazoles in water. NBS, N-bromosuccinamide.…”

“…T A B L E 3 Outline for green solvent-mediated synthesis of thiazole derivatives. [77] 2 -Ethanol 80 12 h 82 [78] 3 Nanochitosan Ethanol Reflux 2.5-4.5 h 75-97 [79] 4 Sulfamic acid Water Reflux 3-6 h 64-89 [80] 5 -Ethanol Reflux 6 h 90-95 [81] 6 F e 3 O 4 @SiO 2 @KIT-6 Water RT 1-2 h 85-97 [82] 7 -PEG-600 RT 4 h 87 [83] 8 K 3 [Fe(CN) 6 ] Ethanol and KOH RT 2 h 80 [84] 9 -Water 90 20 h 65-85 [85] 10 CTAB Glycerol 40 1-3 h 82-96 [86] 11 Fe 3 O 4 @vitamin B 1 Water 80 30-45 min 79-93 [87] 12 -PEG-400 100 2-3.5 h 87-96 [88] 13 GAA PEG-300 70-75 1-1.5 h 82-96 [89] 14 -Water 135 35 min 50-89 [90] 15 Pyridine Water 150 20 h 40-84 [91] 16 -Water 60 1-6 h 65-90 [92] 17 -Glycerin RT 1-2.5 h 87-92 [93] 18 Ca/4-MePy-IL@ZY-Fe 2 O 3 and TCCA Ethanol 80 25 min 85-92 [94] 19 γ-Fe 2 O 3 @HAp@CPTMS@AT@Cu(ӀI) Ethanol RT 20-28 min 88-95 [95] 20 -Ethanol and water RT 60 min 90-98 [96] 21 Citric acid Ethanol and water Reflux 15-40 min 0-96 [97] 22 -Water Reflux 6 h 84-93 [98] 23 ZnO NP Ethanol/neat RT 2-8 min 90-99 [99] 24 PTSA PEG-400 80 2 h 79-95 [100] 25 Fe 2 O 3 NP Water RT 10-32 min 77-90 [101] 26 2-Hydroxypropyl-β-cyclodextrin Water and acetone 50 6 h 41-70 [102] 27 GAA PEG-400 70-75 1-5 h 80-95 [103] 28 Triton X-100 Water RT 5-10 min 85-98 [104] Abbreviations: CTAB, cetyl trimethyl ammonium bromide; GAA, glacial acetic acid; PEG, polyethylene glycol; PTSA, p-toluenesulfonic acid; TCCA, trichloroisocyanuric acid.…”

“…Shaterian and Molaei [ 87 ] established a three‐component one‐pot condensation reaction between arylglyoxal monohydrate, cyclic 1,3‐dicarbonyls, and thiobenzamides in green solvent such as water using reusable Fe 3 O 4 @vitamin B 1 as a heterogeneous nanocatalyst at 80°C for 30–45 min to afford trisubstituted‐1,3‐thiazoles with excellent yield (79%–93%) (Scheme 46).…”

Recent Advances in Multicomponent Reactions Catalysed under Operationally Heterogeneous Conditions

“…A notable life example of a molecule consisting of such rings is luciferin, the compound which allows for the emission of light in fireflies. Vitamin B1 (Figure 19) has been reported to be an efficient catalyst in the formation of trisubstituted 1,3-thiazoles after having been supported on magnetite in a research study by Shaterian et al The reaction entailed a one-pot combination of arylglyoxals monohydrate, cyclic 1,3-dicarbonyls, and thiobenzamides in aqueous conditions at 80 °C (Figure 20) [55]. Yields were superb (78-93%) and reactions took less than 45 min.…”

“…Yields were superb (78-93%) and reactions took less than 45 min. Lastly, the catalyst could be easily removed by a magnet and reused for up to five times [55]. Yields were superb (78-93%) and reactions took less than 45 min.…”