Category: thiazolidine

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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Reference£º
Patent; Yang Wenmao; (12 pag.)CN103387550; (2016); B;,
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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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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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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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Patent; Sankyo Company, Limited; US5298516; (1994); A;,
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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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Patent; Warner-Lambert Company; US5270319; (1993); A;,
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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

Example 6-1 (Z)-3-(5-(2,5-dimethoxybenzylidene)-4-oxo-2-thioxothiazolidin-3-yl)propanoic acid 3-(4-oxo-2-thioxothiazolidin-3-yl)propanoic acid (200 mg, 1 mmol), 2,5-dimethoxy benzaldehyde (168 mg, 1 mmol) and piperidine (0.3 mL) were combined in ethanol (3 mL) and irradiated in the microwave at 100 C. for 10 minutes. The reaction was cooled, the solid was collected by filtration, washed with ethyl acetate/hexanes (1/1) and recrystallized from ethanol to afford 85% yield of the title compound (309 mg, brown-orange solid). MS (M+H, 284); 1H NMR (400 MHz, DMSO-d6): delta, ppm: 2.57 (t, 2H)), 3.74 (s, J=6.8 Hz, 3H), 3.84 (s, 3H), 4.19 (t, 2H), 6.90 (s, 1H), 7.10 (s, 2H), 7.86 (s, 1H).

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Patent; Senomyx, Inc.; US2009/274632; (2009); A1;,
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As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO184,mainly used in chemical industry, its synthesis route is as follows.,5908-62-3

A 40 mL scintillation vial was charged with 1 ,1-dloxo-isothiazolidine (115 mg, 0.949 mmol) and OMF (3 mL). The reaction mixture was cooled to 00C and sodium hydride (95 mg, 2.373 mmol) was added. The reaction was left to stir at room temperature for 20 min foliowed by the addition of 3-bromo~5-(chloromethyl)pyridine hydrochloride (277 mg, 1.139 mmol). The reaction was stirred at room temperature for 3 h, then quenched with water and extracted with ethyi acetate. The organic layer was washed with water twice, dried over sodium sulfate and concentrated in vacuo. The crude was purified by silica gei flash chromatography using heptane-ethyl acetate (6(MO, v/v) to afford 3-bromo-5-(1,1- dioxo-isothiazolidin-2?ylmethyl)?pyridine as a colorless oil. MS (ESI) m/z 292.9 <;M+H)+ With the complex challenges of chemical substances, we look forward to future research findings about 1,1-Dioxo-isothiazolidine,belong thiazolidine compound Reference£º
Patent; NOVARTIS AG; CHAMOIN, Sylvie; HU, Qi-Ying; PAPILLON, Julien; WO2010/130796; (2010); A1;,
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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 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.

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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-(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

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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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 quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO273,mainly used in chemical industry, its synthesis route is as follows.,5908-62-3

Compound 20: N-(3-(9H-Carbazol-9-yl)-2-hydroxypropyl)isothiazolidine 1,1-dioxide To a stirred solution of 1,3-propanesultam (0.80 g, 6.6 mmol) in anhydrous N,N-dimethylformaide (20 mL) was added sodium hydride (60% in mineral oil, 0.053 g, 1.3 mmol) and the mixture was stirred at room temperature for 1 hour. 9-(Oxiran-2-ylmethyl)-9H-carbazole (1.622 g, 7.3 mmol) was added and the mixture was stirred at 70 C. overnight. After cooling, the reaction was diluted with water and extracted three times with ethyl acetate. The combined organic layers were washed with saturated aqueous sodium chloride, dried (anhydrous sodium sulfate), filtered, and concentrated. The residue was purified by silica gel column chromatography (0-70% ethyl acetate in hexanes) and then recrystallized from ethyl acetate/hexanes to give the pure compound as a white solid (1.6 g, 70%). 1H NMR (300 MHz, CDCl3) delta 8.10 (d, 2H, J=7.5 Hz), 7.48 (d, 4H, J=3.9 Hz), 7.30-7.22 (m, 2H), 4.55-4.35 (m, 3H), 3.42-3.12 (m, 6H), 2.59 (d, 1H, J=3.0 Hz), 2.37 (m, 2H). ESI (m/z): 344.9 (M+H). HPLC analysis: (C18, 10-90% acetonitrile in water+0.1% trifluoroacetic acid over 10 min: retention time, % area at 254 nm): 11.8 min, >98%.

With the synthetic route has been constantly updated, we look forward to future research findings about 1,1-Dioxo-isothiazolidine,belong thiazolidine compound

Reference£º
Patent; Bersot, Ross; Humphries, Paul; US2013/303524; (2013); A1;,
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