Heterocyclic Building Blocks-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

To a 500 ml three-necked flask, 38.1 g (0.3 mol) of 2-cyanoimino-1,3-thiazolidine, 82.8 g (0.6 mol) of potassium carbonate, 1.9 g (0.006 mol) of tetrabutylammonium bromide, and Water 220 g followed by the slow dropwise addition of 57.6 g (0.36 mol) of 2-chloro-5-chloromethylpyridine. The duration of the slow addition was 1.5 hours; the reaction was stirred at 60C for 2.5 hours.The reaction was completely detected, stirred and cooled to precipitate a large amount of solids, suction filtration, and cake was taken to obtain 68.8 g of thiacloprid with a purity of 96.5% and a yield of 88.2%; wherein the filtrate obtained by suction filtration (including water and catalyst) was obtained. Tetrabutylammonium bromide) is applied to the next batch of reactions (implementation)Example 6).

With the complex challenges of chemical substances, we look forward to future research findings about 2-Cyanoimino-1,3-thiazolidine

Reference£º
Patent; Shanghai Sheng Nong Biochemical Goods Co., Ltd.; Ye Zhenjun; Geng Li; Fang Yan; Han Haiping; (6 pag.)CN107629045; (2018); A;,
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It is a common heterocyclic compound, the thiazolidine compound, 3-(4-Oxo-2-thioxothiazolidin-3-yl)propanoic acid, 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.

With the complex challenges of chemical substances, we look forward to future research findings about 3-(4-Oxo-2-thioxothiazolidin-3-yl)propanoic acid

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 quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO451,mainly used in chemical industry, its synthesis route is as follows.,1438-16-0

General procedure: A mixture of aminorhodanine (1 mmol), isatin (1 mmol) and 5 muL of acetic acid in 2mL of distilled ethanol was placed in a cylindrical quartz reactor (Phi = 4 cm). The reactor was introducedinto a monomode microwave (Anton Paar) apparatus, for 5 min at100 C and 50 Watts. The crude reaction mixture was allowed tocool down at room temperature and ethanol (10 mL) or mixture of H2O/EtOH (10 mL) was directly added in the cylindrical quartzreactor. The resulting precipitated product was filtered off and waspurified by recrystallization from ethanol if necessary.

With the synthetic route has been constantly updated, we look forward to future research findings about 3-Aminorhodanine,belong thiazolidine compound

Reference£º
Article; Khaldoun, Khadidja; Safer, Abdelmounaim; Boukabcha, Nourdine; Dege, Necmi; Ruchaud, Sandrine; Souab, Mohamed; Bach, Stephane; Chouaih, Abdelkader; Saidi-Besbes, Salima; Journal of Molecular Structure; vol. 1192; (2019); p. 82 – 90;,
Thiazolidine – Wikipedia
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As a common heterocyclic compound, it belongs to thiazolidine compound, name is 1,1-Dioxo-isothiazolidine, and cas is 5908-62-3, its synthesis route is as follows.,5908-62-3

To a solution of 2-((S)-3-((S)-1-(4-bromophenyl)ethyl)-2-oxo-6-phenyl-1,3-oxazinan-6-yl)ethyl-methanesulfonate (360 mg, 0.75 mmol) and K2CO3 (207 mg, 1.5 mmol) in acetonitrile (10 mL) was added isothiazolidine 1,1-dioxide (121 mg, 4.6 mmol), and the mixture was refluxed overnight. The mixture was filtered and the filtrate was concentrated to give the crude product, which was purified by preparative HPLC to afford compound (S)-3-((S)-1-(4-bromophenyl)ethyl)-6-(2-(1,1-dioxo-isothiazolidin-2-yl)ethyl)-6-phenyl-1,3-oxazinan-2-one (2.43 mg, 1%). LC-MS Method 2 tR=1.37 min, m/z=509, 507. 1H NMR (CDCl3): 1.48 (t, 3H), 2.05-2.41 (m, 7H), 2.71-2.92 (m, 2H), 3.11 (m, 3H), 3.21 (m, 2H), 5.58 (m, 1H), 6.73 (d, 2H), 7.18 (m, 1H), 7.23 (m, 3H); 7.35 (m, 3H).

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Reference£º
Patent; Vitae Pharmaceuticals, Inc.; Boehringer Ingelheim International GmbH; US2010/331320; (2010); A1;,
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Name is 3-Aminorhodanine, as a common heterocyclic compound, it belongs to thiazolidine compound, and cas is 1438-16-0, its synthesis route is as follows.,1438-16-0

General procedure: General procedure for synthesis of N-substituted-rhodanine derivatives RhAs: To a solution of aldehydes (3a-3h, 1.0 equiv.) in ethanol (10 mL) was added slowly to the solution of 3-amino-2-thioxothiazolidin-4-one (2, 1.0 equiv.) in EtOH. The reaction mixture was stirred at room temperature without a catalyst for between 4 h and 12 h, and was monitored by TLC. After, the mixture product was recrystallized from EtOH. After recrystallization, N-substituted-rhodanine derivatives (RhAs) were obtained as follows.

With the complex challenges of chemical substances, we look forward to future research findings about 3-Aminorhodanine

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Article; Bayindir; Caglayan, Cuneyt; Karaman, Muhammet; Guelcin, ?lhami; Bioorganic Chemistry; vol. 90; (2019);,
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Thiazolidine hydrochloride, cas is 14446-47-0, it is a common heterocyclic compound, the thiazolidine compound, its synthesis route is as follows.,14446-47-0

EXAMPLE 58 Preparation of 1-(4-bromophenyl)-3-(3-thiazolidinyl)propan-1-one 12.56 g (0.1 mol) of thiazolidine hydrochloride, 19.9 g (0.1 mol) of 4-bromoacetophenone, 12 ml of 36% formaldehyde solution (0.144 mol), 30 ml of ethanol and 5 drops of concentrated hydrochloric acid are mixed and then heated. After a short reflux period, a homogeneous solution is formed. After a 7-hour boiling, the solution is evaporated, the oily residue is poured into 1000 ml of acetone under stirring and the precipitated starting material is filtered off. After evaporating the filtrate, the residue is recrystallized from ethanol or methanol to give the hydrochloride of the title compound, m.p.: 170 C.

14446-47-0 is used more and more widely, we look forward to future research findings about Thiazolidine hydrochloride

Reference£º
Patent; Richter Gedeon Vegyeszeti Gyar Rt.; US5096902; (1992); A;,
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As a common heterocyclic compound, it belongs to thiazolidine compound, name is 1,1-Dioxo-isothiazolidine, and cas is 5908-62-3, its synthesis route is as follows.,5908-62-3

Intermediate 96To an oven dried 50 mL round-bottom flask, methyl 2-bromo-5-methylbenzoate (352 mg, 1.54 mmol), sultam (236 mg, 1.95 mmol), cesium carbonate (732 mg, 2.25 mmol), palladium acetate (40.4 mg, 0.18 mmol), and Xanphos (136 mg, 0.235 mmol) were added and flask was placed under argon. Reagents were suspended in 8 mL of anhydrous dioxane and mixture was heated at 100 C overnight. After cooling to room temperature, reaction mixture was filtered, washing with ethyl acetate. Combined filtrate was concentrated under reduced pressure and resulting film was purified by silica gel column chromatography (25-100% Ethyl Acetate in Hexanes) to yield intermediate 96 (322 mg, 78%) as a yellow off-white solid.1H-NMR (DMSO, 400 MHz): delta 7.75 (d, 1H), 7.44 (m, 1H), 7.35 (m, 1H), 3.89 (s, 3H), 3.81 (t,2H), 3.28 (t, 2H), 2.55 (m, 2H), 2.39 (s, 3H).LCMS m/z [M+H]+ Ci2H15N04S requires: 270.07. Found 270.12.

With the complex challenges of chemical substances, we look forward to future research findings about 5908-62-3,belong thiazolidine compound

Reference£º
Patent; GILEAD SCIENCES, INC.; BABAOGLU, Kerim; BOOJAMRA, Constantine, G.; EISENBERG, Eugene, J.; HUI, Hon Chung; MACKMAN, Richard, L.; PARRISH, Jay, P.; SANGI, Michael; SAUNDERS, Oliver, L.; SIEGEL, Dustin; SPERANDIO, David; YANG, Hai; WO2011/163518; (2011); A1;,
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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

General procedure: To a reaction vessel was added compound19(70 mg, 0.16 mmol), thiazolidine-2,5-dione (28 mg, 0.25 mmol), piperidine (2 muL, 0.02 mmol) and acetic acid (1 muL, 0.02 mmol) in the presence of toluene. The reaction mixture was refluxed overnight and the reaction solvent was removed by evaporation. The residual was dissolved in EtOAc and washed with H2O (2 x 10 mL) and brine. The organic layer was collected, dried over anhydrous Na2SO4, filtered, concentrated and purifiedby silica gel column chromatography using 20% EtOAc in hexanes to afford compound20(57 mg, 66%).

With the complex challenges of chemical substances, we look forward to future research findings about 1438-16-0,belong thiazolidine compound

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Article; Kim, Hyojin; Cho, Suk Joon; Yoo, Minjin; Kang, Seung Kyu; Kim, Kwang Rok; Lee, Hwan Hee; Song, Jin Sook; Rhee, Sang Dal; Jung, Won Hoon; Ahn, Jin Hee; Jung, Jae-Kyung; Jung, Kwan-Young; Bioorganic and Medicinal Chemistry Letters; vol. 27; 23; (2017); p. 5213 – 5220;,
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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 tetrazoloquinoline aldehyde 1a (1 mmol) and rhodanine 2a (1 mmol), 20 mol % [HDBU][HSO4] was added, and the mixture was heated on an oil bath at 80 C for 30 min. During the reaction process, the mixture was solidified and after completion of the reaction (monitored by TLC), the reaction was cooled to room temperature, water was added and stirred for 5 min. The solid obtained was removed by filtration and recrystallized from EtOH-DMF. The filtrate was dried under reduced pressure to recover ionic liquid and reused in subsequent cycles.

With the complex challenges of chemical substances, we look forward to future research findings about 7025-19-6,belong thiazolidine compound

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Article; Subhedar, Dnyaneshwar D.; Shaikh, Mubarak H.; Nawale, Laxman; Yeware, Amar; Sarkar, Dhiman; Khan, Firoz A. Kalam; Sangshetti, Jaiprakash N.; Shingate, Bapurao B.; Bioorganic and Medicinal Chemistry Letters; vol. 26; 9; (2016); p. 2278 – 2283;,
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(S)-4-Phenylthiazolidine-2-thione, cas is 185137-29-5, it is a common heterocyclic compound, the thiazolidine compound, its synthesis route is as follows.,185137-29-5

General procedure: Thiazolidine-2-thione 2 (2.5 mmol), benzyl chloride (317 mg, 2.5 mmol), and K2CO3(691 mg, 5 mmol) were dissolved in 10 mL of acetone. The resulting solution was refluxedfor 2-4 h under TLC monitoring and then was allowed to cool to r.t. and filtered. Afterremoval of the solvent, the crude product was obtained and purified by silica-gel columnchromatography with a mixture of petroleum ether and EtOAc (10:1, v/v) as eluent.

185137-29-5 is used more and more widely, we look forward to future research findings about (S)-4-Phenylthiazolidine-2-thione

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Article; Chen, Ning; Du, Hongguang; Liu, Weidong; Wang, Shanshan; Li, Xinyao; Xu, Jiaxi; Phosphorus, Sulfur and Silicon and the Related Elements; vol. 190; 1; (2015); p. 112 – 122;,
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