Heterocyclic Building Blocks-Thiazolidine

As a common heterocyclic compound, it belongs to thiazolidine compound, name is Thiazolidin-2-one, and cas is 2682-49-7, its synthesis route is as follows.,2682-49-7

Example 61 1-phenyl-3-(3-thiazolidinyl)propan-1-one A solution containing 8.43 g (0.05 mol) of beta-chloropropiophenone, 4.10 g (0.05 mol) of anhydrous sodium acetate and 4.01 g (0.045 mol) of thiazolidone in 30 ml of ethanol is stirred at 25C for 8 hours. After filtering off the precipitate and evaporating the solvent from the solution, the oily yellowish residue weighing 9.3 g is converted to the hydrochloride salt in a mixture of acetone and ether in the usual way to give 9.9 g of product. After recrystallization from methanol, the hydrochloride of the title product thus obtained melts at 170-171C; it is identical to the hydrochloride salt of Examples 1 and 43 above.

With the complex challenges of chemical substances, we look forward to future research findings about Thiazolidin-2-one

Reference£º
Patent; RICHTER GEDEON VEGYESZETI GYAR R.T.; EP411775; (1991); A1;,
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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 stirred solution of 5-{9-fluoro-6-methanesulfonyl-5-[(S)-oxan-4- y l(pheny l)methy 1] -5H-py rido [3,2-b] indol-3 -y 1 } – 1 ,4-dimethy 1- 1H- 1 ,2,3-triazole (25.0 mg 0.0500 mmol) and isothiazolidine-l,l-dione (5.7 mg, 0.0500 mmol) in DMF (0.25 mL) was added t-BuOK (21.0 mg, 0.190 mmol). This mixture was heated at 65 C for 1.5 h and cooled to room temperature. The mixture was then diluted with MeOH and purified via preparative LC/MS with the following conditions: Column: Waters XBridge Phenyl, 19 x 200 mm, 5-mutaueta particles; Mobile Phase A: 5:95 ACN: water with 10 mM NH4OAC; Mobile Phase B: 95:5 ACN: water with 10 mM NH4OAc; Gradient: 15-70% B over 20 min, then a 5-min hold at 100% B; Flow: 20 mL/min. Fractions containing the desired product were combined and dried via centrifugal evaporation to give 2-[3-(dimethyl-lH- l,2,3-triazol-5-yl)-6-methanesulfonyl-5-[(S)-oxan-4-yl(phenyl)methyl]-5H-pyrido[3,2- b]indol-9-yl]- 6,2-thiazolidine-l,l-dione (12.3 mg, 41%). NMR (500MHz, DMSO- de) delta 8.72 (s, IH), 8.38 (d, J=8.4 Hz, IH), 7.88 (s, IH), 7.62 (br d, J=8.4 Hz, 3H), 7.36- 7.30 (m, 2H), 7.27 (br d, J=7.1 Hz, IH), 6.81 (br d, J=10.1 Hz, IH), 4.11 (br d, J=2.0 Hz, 2H), 3.86 (br d, J=9.8 Hz, IH), 3.76 (s, 3H), 3.74 (s, 2H), 3.64 (br d, J=8.8 Hz, IH), 3.57 (br t, J=7.4 Hz, IH), 3.19 (br t, J=12.1 Hz, IH), 2.65-2.57 (m, 2H), 2.54 (s, 3H), 2.07 (s, 3H), 1.95 (br d, J=12.5 Hz, IH), 1.75-1.56 (m, 2H), 0.42 (br d, J=12.1 Hz, IH). LCMS: RT = 1.414 min; (ES): m/z (M+H)+ = 634.95; LCMS: Column: Waters Acquity UPLC BEH C18, 2.1 x 50 mm, 1.7-muiotaeta particles; Mobile Phase A: 5:95 ACN:water with 10 mM NH4OAc; Mobile Phase B: 95:5 ACN:water with 10 mM NH4OAC; Temperature: 50 C; Gradient: 0-100% B over 3 min, then a 0.75-min hold at 100% B; Flow: 1.11 mL/min. HPLC Purity at 220 nm: 100 %

With the complex challenges of chemical substances, we look forward to future research findings about 1,1-Dioxo-isothiazolidine

Reference£º
Patent; BRISTOL-MYERS SQUIBB COMPANY; HAN, Wen-Ching; DEGNAN, Andrew P.; DESKUS, Jeffrey A.; GAVAI, Ashvinikumar V.; GILL, Patrice; SCHMITZ, William D.; STARRETT, John E., Jr.; (193 pag.)WO2016/183115; (2016); A1;,
Thiazolidine – Wikipedia
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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: The suspension of 2-thioxo-1,3-thiazolidin-4-one (0.01 mol) 1a-40a in ethanol (50 mL) was mixed under stirring with a solution of aldehyde (0.011 mol) 1b-40b followed by the addition 3 drops of piperidine under the reflux conditions. The resulting mixture was heated under reflux until complete disappearance of 2-thioxo-1,3-thiazolidin-4-one, TLC control CH3OH – EtOAc 1:9. The reaction mixture was diluted with water (75 mL) and filtrated. The solid residue was recrystallized from a mixture of IPA/DMF.

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; Volynets, Galyna P.; Bdzhola, Volodymyr G.; Golub, Andriy G.; Synyugin, Anatoliy R.; Chekanov, Maksym A.; Kukharenko, Oleksandr P.; Yarmoluk, Sergiy M.; European Journal of Medicinal Chemistry; vol. 61; (2013); p. 104 – 115;,
Thiazolidine – Wikipedia
Thiazolidine – ScienceDirect.com

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

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 3-(4-Oxo-2-thioxothiazolidin-3-yl)propanoic acid

Reference£º
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;,
Thiazolidine – Wikipedia
Thiazolidine – ScienceDirect.com

As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO450,mainly used in chemical industry, its synthesis route is as follows.,171877-39-7

To a solution of (S)-4-benzylthiazolidine-2-thione (1 g, 4.78 mmol) in THF (dry, 50 mL) was added n-BuLi (2.87 mL, 7.17 mmol, 2.5 M) at – 78 C. The resulting mixture was stirred at that temperature for 1 .5 h, then 2-cyclohexylacetyl chloride (1 .10 ml, 7.17 mmol) was added. The temperature was maintained at – 78 C for 2.5 h. Then the reaction mixture was allowed to warm to RT and stirred for 16 h. After an aqueous work up with saturated NH4CI solution the crude product was purified by flash chromatography (cyclohexane) to afford 29 as a yellow crystalline solid (1 .48 g, 4.45 mmol, 93 %). TLC [cyclohexane/EE, 8:2]: Rf = 0.6 Mass (ESI+), calculated 333.12 [C18H23NOS2 + H]+, found = 334.04 [M+H]+

With the synthetic route has been constantly updated, we look forward to future research findings about (S)-4-Benzylthiazolidine-2-thione,belong thiazolidine compound

Reference£º
Patent; MAX-PLANCK-GESELLSCHAFT ZUR FOeRDERUNG DER WISSENSCHAFTEN E.V.; GAALI, Steffen; HAUSCH, Felix; KIRSCHNER, Alexander; FENG, Xiri; BRACHER, Andreas; RUEHTER, Gerd; WO2015/39758; (2015); A1;,
Thiazolidine – Wikipedia
Thiazolidine – ScienceDirect.com

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

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
Thiazolidine – ScienceDirect.com

As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO471,mainly used in chemical industry, its synthesis route is as follows.,19771-63-2

25(a) (4R)-N-(4-Hydroxybutyl)-2-oxothiazolidine-4-carboxamide Following a procedure similar to that described in Example 16(a), but using 1.2 g of (4R)-2-oxothiazolidine-4-carboxylic acid and 2.23 g of N-(4-hydroxybutyl)amine, 0.735 g of the title compound was obtained as colorless crystals, melting at 81-83 C. Nuclear Magnetic Resonance Spectrum (CDCl3 +hexadeuterated dimethyl sulfoxide) delta ppm:

With the synthetic route has been constantly updated, we look forward to future research findings about (R)-2-Oxothiazolidine-4-carboxylic acid,belong thiazolidine compound

Reference£º
Patent; Sankyo Company, Limited; US5298516; (1994); A;,
Thiazolidine – Wikipedia
Thiazolidine – ScienceDirect.com

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

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;,
Thiazolidine – Wikipedia
Thiazolidine – ScienceDirect.com

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 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 3-(4-Oxo-2-thioxothiazolidin-3-yl)propanoic acid

Reference£º
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;,
Thiazolidine – Wikipedia
Thiazolidine – ScienceDirect.com

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

General procedure: To a solution of 1,3-diaryl-4-formylpyrazoles 4 (1.0 mmol) and rhodanine analogs 5 (1.0 mmol) in absolute ethanol (8.0 mL) was added drops of acetic acid and piperidine. The reaction mixture was stirred at 40-50 C, until the completion of the reaction as evidenced by TLC. After the solution was cooled, the resulting reaction mixture was ltered off and crude product was purified by 95% ethanol to afford pure products 6-29. The yield, melting point and spectral data of each compound are given below.

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; Xu, Li-Li; Zheng, Chang-Ji; Sun, Liang-Peng; Miao, Jing; Piao, Hu-Ri; European Journal of Medicinal Chemistry; vol. 48; (2012); p. 174 – 178;,
Thiazolidine – Wikipedia
Thiazolidine – ScienceDirect.com