Heterocyclic Building Blocks-Thiazolidine

As a common heterocyclic compound, it belongs to thiazolidine compound, name is 3-(4-Oxo-2-thioxothiazolidin-3-yl)propanoic acid, and cas is 7025-19-6, its synthesis route is as follows.,7025-19-6

General procedure: To a mixture of aldehyde (1.0 mmol), 3-(4-oxo-2-thioxothiazolidin-3-yl)propanoic acid (205 mg,1.0 mmol) or 3-(2-(1H-tetrazol-5-yl)ethyl)-2-thioxothiazolidin-4-one (229 mg, 1.0 mmol) and NaOAc (820 mg, 10.0 mmol) was added acetic acid (5.0 mL). The reaction was allowed to stir at 105 C for 0.5h – 12h, then cooled to room temperature. To the reaction was added water (15mL). The resulting mixture was sonicated to give yellow-orange slurry. After filtration, the solid was washed with water (75 mL) and dried under high vacuum to yield the corresponding product as a red fine powder.

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Reference£º
Article; Liang, Dongdong; Robinson, Elizabeth; Hom, Kellie; Yu, Wenbo; Nguyen, Nam; Li, Yue; Zong, Qianshou; Wilks, Angela; Xue, Fengtian; Bioorganic and Medicinal Chemistry Letters; vol. 28; 6; (2018); p. 1024 – 1029;,
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As a common heterocyclic compound, it belongs to thiazolidine compound, name is (S)-4-Phenylthiazolidine-2-thione, and cas is 185137-29-5, its synthesis route is as follows.,185137-29-5

General procedure: To thiazolidine-2-thiones (1.0 equiv.) in THF (5.5 mL/mmol), 60% NaH dispersion in mineral oil (1.2 equiv.)was slowly added at 0 C. The reaction mixture was stirred for 15 min at 0 C before acetyl chloride (1.2 equiv.)was added dropwise. The reaction mixture was stirred for 30 min at 0 C, upon which it was warmed to roomtemperature and allowed to stir for another 2 h. The reaction was quenched with saturated NH4Cl (3 mL/mmol)and the layers were separated. The aq. layer was extracted with EtOAc (2 x 4 mL/mmol) and the combinedorganic layers were dried (Na2SO4),filtered, and concentrated in vacuo. The crude product was purified bycolumn chromatography on silica (hexanes/EtOAc 8:2) to afford the title compounds as yellow oils.

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Reference£º
Article; Tungen, J¡ãrn E.; Aursnes, Marius; Hansen, Trond Vidar; Tetrahedron Letters; vol. 56; 14; (2015); p. 1843 – 1846;,
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As a common heterocyclic compound, it belongs to thiazolidine compound, name is 3-Aminorhodanine, and cas is 1438-16-0, its synthesis route is as follows.,1438-16-0

EXAMPLE 48 2-Thioxo-3-[[5-(trifluoromethyl)-1,3-benzodithiol-2-ylidene]amino]-4-thiazolidinone A slurry of 3.0 g of N-methyl-N-[5-(trifluoromethyl)-1,3-benzodithiol-2-ylidene]benzaminium iodide, N-aminorhodanine (982 mg) and sodium carbonate (351 mg) in 100 ml of anhydrous dimethylformamide is heated at 120 C for 2 hours. The reaction mixture is chilled in an ice bath and the resultant precipitate collected by filtration. This product is recrystallized from dimethylformamide to yield 570 mg of the title compound, melting point 285-288 C. Anal. Calc’d. for C11 H5 F3 N2 OS4: C, 36.06; H, 1.38; N, 7.65; S, 35.00; F, 15.56. Found: C, 36.14; H, 1.26; N, 7.89; S, 35.16; F, 15.61.

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Reference£º
Patent; E. R. Squibb & Sons, Inc.; US4104467; (1978); A;,
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3-(4-Oxo-2-thioxothiazolidin-3-yl)propanoic acid, cas is 7025-19-6, it is a common heterocyclic compound, the thiazolidine compound, its synthesis route is as follows.,7025-19-6

To a mixture of 3-(4-oxo-2-thioxothiazolidin-3-yl)propanoic acid (205 mg, 1.0 mmol), H2N-Gly-OEt hydrochloride (140 mg, 1.0 mmol) and EDC (192 mg, 1.0 mmol) in DMF (5.0 mL) was added triefhylamine (140 muEpsilon, 1.0 mmol). The reaction mixture was stirred at room temperature for 16 h, and then concentrated. The crude product was purified by flash chromatogrphy (EtOAc/Hexanes 1 :2- 1 :1) to give FX-3019 as a white solid (276 mg, 0.95 mmol, 95%): :H NMR (400 MHz, DMSO-de) delta 1.25-1.30 (t, 7 = 6.8 Hz, 3H), 2.64-2.70 (t, 7 = 7.6 Hz, 2H), 4.01 (s, 3H), 4.20-4.25 (dd, 7= 7.2, 14.0 Hz, 2H), 4.25-4.35 (t, 7 = 8.0 Hz, 2H), 6.04 (s, 1H); 13C NMR (100 MHz, DMSO-de) delta 14.1, 32.7, 35.4, 40.6, 41.4, 61.7, 169.4, 169.8, 173.6, 201.0; LC-TOF (M+H+) calcd for C10H15N2O4S2 291, found 291. Chemical Formula: C18H16BrN305S2

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Reference£º
Patent; MELNICK, Ari; CERCHIETTI, Leandro, Carlos, A.; CARDENAS, Mariano, G.; XUE, Fengtian; MACKERELL, Alexander, D.; WO2014/204859; (2014); A2;,
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As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO420,mainly used in chemical industry, its synthesis route is as follows.,7025-19-6

General procedure: To a mixture of 5-chloroisatin (182 mg, 1.0 mmol) and N-carboxyethylrhodanine (205 mg, 1.0 mmol) was added DMSO-d6 (3.0 mL). The reaction was followed by proton NMR until the disappearance of the starting material.

With the synthetic route has been constantly updated, we look forward to future research findings about 3-(4-Oxo-2-thioxothiazolidin-3-yl)propanoic acid,belong thiazolidine compound

Reference£º
Article; Xue, Fengtian; MacKerell Jr., Alexander D.; Heinzl, Geoffrey; Hom, Kellie; Tetrahedron Letters; vol. 54; 13; (2013); p. 1700 – 1703;,
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3-Aminorhodanine, cas is 1438-16-0, it is a common heterocyclic compound, the thiazolidine compound, its synthesis route is as follows.

EXAMPLE 12 5-[4,6-Bis(1,1-dimethylethyl)-5-hydroxy-2-pyrimidinyl]methylene]-3-amino-2-thioxo-4-thiazolidinone A mixture of 4,6-bis(1,1-dimethylethyl)-5-hydroxy-2-pyrimidine carboxaldehyde (1.00 g, 4.23 mmol), sodium acetate (1.36 g, 16.6 mmol), and 3-aminorhodanine (0.63 g, 4.3 mmol) in glacial acetic acid (15 mL), under nitrogen atmosphere, is warmed to reflux and refluxed 7 hours. This mixture is then cooled to room temperature and stirred 16 hours. After stirring, the reaction mixture is diluted with a 1:2 mixture of ethanol and water and extracted with ethyl acetate. The combined organic extracts are washed with water, aqueous 0.2N hydrochloric acid solution, and brine. The organic phase is dried over magnesium sulfate, concentrated, and purified by flash chromatography (SiO2, 20% ethyl acetate/hexane) followed by recrystallization from methanol and water to give 0.42 g (27%) of the title compound, mp 194-196 C., 1438-16-0

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Reference£º
Patent; Warner-Lambert Company; US5270319; (1993); A;,
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It is a common heterocyclic compound, the thiazolidine compound, (R)-2-Oxothiazolidine-4-carboxylic acid, cas is 19771-63-2 its synthesis route is as follows.,19771-63-2

EXAMPLE 18 (4R)-N-(2-Nitrooxypropyl)-2-oxothiazolidine-4-carboxamide (Compound No. 1-31) A procedure similar to that described in Example 1 was repeated, but using 2.0 g of (4R)-2-oxothiazolidine-4-carboxylic acid and 3.0 g of N-(2-nitrooxypropyl)amine nitrate, to obtain 24 mg of the title compound as pale yellow crystals, melting at 70-72 C. (after recrystallization from ethanol).

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Reference£º
Patent; Sankyo Company, Limited; US5298516; (1994); A;,
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Name is 2-Cyanoimino-1,3-thiazolidine, as a common heterocyclic compound, it belongs to thiazolidine compound, and cas is 26364-65-8, its synthesis route is as follows.,26364-65-8

General procedure: Thiazolidin-2-ylidene-cyanamide (0.317 g, 2.50 mmol) inacetonitrile (20 mL) was dropwise added to a stirred solutionof substituted benzyl bromide (2.5 mmol) and 14 mL NaOHaqueous solution (1 M). The mixture is stirred at room temperaturefor 8-10 h. The soild was collected by filtration,washed with n-hexane and dried in vacuo.

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Article; Jia, Ai-Quan; Ma, Sen; Wang, Jun-Ling; Zhang, Qian-Feng; Journal of Chemical Crystallography; (2020);,
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Name is 3-(4-Oxo-2-thioxothiazolidin-3-yl)propanoic acid, as a common heterocyclic compound, it belongs to thiazolidine compound, and cas is 7025-19-6, its synthesis route is as follows.,7025-19-6

To a solution of 3.0 g (11.4 mmol) of an aldehyde derivative (1) in 20 mL of acetic acid were added 2.2 g (11.5 mmol) of rhodanine-3-propionic acid and 0.9 g of ammonium acetate, followed by stirring under reflux for 2 hours. After completion of the reaction, 50 mL of water were slowly added dropwise thereto while cooling, and the mixture was cooled to room temperature. A solid precipitate was filtrated, washed twice with 100 mL of water, and further washed with 50 mL of 2-propanol, to afford 3.1 g (yield: 60.1%) of a target product (4).

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Patent; CANON KABUSHIKI KAISHA; Tanaka, Toshio; Watanabe, Kohei; Nomoto, Tsuyoshi; Okano, Mie; Shintou, Taichi; Miyazaki, Takeshi; Nishimura, Yuhei; Shimada, Yasuhito; (39 pag.)US10227337; (2019); B2;,
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As a common heterocyclic compound, it belongs to thiazolidine compound, name is 2-Cyanoimino-1,3-thiazolidine, and cas is 26364-65-8, its synthesis route is as follows.,26364-65-8

Under nitrogen protection, add 25g (0.197mol) HRB-1365-2 to the three-necked bottle.(2-cyanoimino-1,3-thiazolidine molecular formula: C4H5N3S) compound, adding 300 mL of methanol,With stirring, 23 g of triethylamine was added, and 26 g (0.230 mol) was added.Compound HRB-1365-1 (Cysteamine molecular formula:C2H7NS), stir the reaction at room temperature for four hours,After LC-MS was monitored, the methanol was distilled off under reduced pressure and the solid was filtered.The solid distilled water was washed with 50 ml, and dried to obtain a white solid HRB-1365 (amino thiol thiazoline molecular formula: C6H9N3S2) 16 g,

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Patent; Yang Wenmao; (12 pag.)CN103387550; (2016); B;,
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