2020年9月25日 | Heterocyclic Building Blocks-Thiazines

A new synthetic route of 2-(Trifluoromethyl)-10H-phenothiazine

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,92-30-8,2-(Trifluoromethyl)-10H-phenothiazine,its application will become more common.

A common heterocyclic compound, 92-30-8,2-(Trifluoromethyl)-10H-phenothiazine, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route. 92-30-8

To a solution of 2-(trifluoromethyl)-10H-phenothiazine (5.0g, 18.8mmol) and DMF (15mL) at RT was added finely powdered KOH (2.1g, 37.5mmol) and (¡À)-epibromohydrin (3.9mL, 48.9mmol). The reaction mixture was stirred at RT for 48h. Once no starting material was observed by analytical LCMS, EtOAC (250mL) and brine (250mL) were added. The organic layer was separated, and the aqueous layer was washed with EtOAC (3 chi lOOmL). The combined organic extracts were washed with brine (2 chi lOOmL), dried over MgSOzi, and concentrated to afford the title compound

Reference£º
Patent; INCEPTION 1, INC.; CHEN, Austin, Chih-Yu; SCOTT, Jill, Melissa; STEARNS, Brian, Andrew; STOCK, Nicholas, Simon; TRUONG, Yen, Pham; WO2013/43744; (2013); A2;,
Thiazine – an overview | ScienceDirect Topics
Thiazine | C4H5NS – PubChem

New downstream synthetic route of 3939-23-9

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,3-Bromo-10H-phenothiazine,3939-23-9,its application will become more common.

A common heterocyclic compound, 3939-23-9,3-Bromo-10H-phenothiazine, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route. 3939-23-9

In a 250 ml three-necked flask, 0.01 mol of raw material A1, 0.012 mol of raw material B1, 150 ml of toluene were added under a nitrogen atmosphere, and the mixture was stirred and mixed.Then, 0.03 mol of sodium t-butoxide, 5 ¡Á 10 -5 mol of Pd 2 (dba) 3, 5 ¡Á 10 -5 mol of tri-tert-butylphosphine was added, and the mixture was heated to 105 C, and refluxed for 24 hours.The sampling point plate shows that no raw material A1 remains, the reaction is complete; it is naturally cooled to room temperature, filtered, and the filtrate is steamed to a non-fraction (-0.09 MPa, 85 C) under reduced pressure, and passed through a neutral silica gel column to obtain an intermediate B1.HPLC purity 99.2%, yield 75.2%;

Reference£º
Patent; Jiangsu March Optoelectric Technology Co., Ltd.; Tang Dandan; Zhang Zhaochao; Li Chong; Zhang Xiaoqing; (44 pag.)CN108218853; (2018); A;,
Thiazine – an overview | ScienceDirect Topics
Thiazine | C4H5NS – PubChem

The origin of a common compound about 92-30-8

After dissolving 2-(trifluoromethyl)-10H-phenothiazine (2.0 g, 7.48 mmol) in N,N-dimethylformamide (2 mL), 60% sodium hydride (149.70 mg, 3.74 mmol) and 1-bromo-4-chlorobutane (1.16 mL, 10.10 mmol) were added at 0 C. The reactants were heated at 100 C. for 12 hours under reflux. After the reaction was completed, the reaction solution was extracted with ethyl acetate and the organic layer was dried with magnesium sulfate, filtered under reduced pressure and then concentrated under reduced pressure. The target compound (1.52 g) was obtained with a yield of 56.72% by separating the residue by chromatography (ethyl acetate/n-hexane=1/20). 1H NMR (400 MHz, CDCl3): delta 1.89-2.00 (4H, m, 2CH2), 3.40 (1H, t, J=6.02 Hz, CH), 3.54 (1H, t, 6.18 Hz, CH), 3.94 (2H, t, 6.02 Hz, CH2), 6.89 (1H, d, J=8.12 Hz, CH), 6.96 (1H, t, 7.44 Hz, CH) 7.03 (1H, s, CH), 7.13-7.17 (2H, m, 2CH), 7.21 (2H, t, 8.16 Hz, 2CH).

Reference£º
Patent; Korea Institute of Science and Technology; Roh, Eun Joo; Jeon, Bo Ra Mi; Lee, Chang Joon; Hong, Jin Pyo; Jeong, Joo Yeon; Kang, Sang Soo; (28 pag.)US10035795; (2018); B1;,
Thiazine – an overview | ScienceDirect Topics
Thiazine | C4H5NS – PubChem

New downstream synthetic route of 98827-44-2

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,Methyl 4-hydroxy-2H-thieno[2,3-e][1,2]thiazine-3-carboxylate 1,1-dioxide,98827-44-2,its application will become more common.

A common heterocyclic compound, 98827-44-2,Methyl 4-hydroxy-2H-thieno[2,3-e][1,2]thiazine-3-carboxylate 1,1-dioxide, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route. 98827-44-2

EXAMPLE 6 A solution of 4-hydroxy-3-methoxycarbonyl-2H-thieno-[2,3-e]-1,2-thiazine 1,1-dioxide (0.7 g) and 2-aminotropone (0.341 g) in xylene (7 ml) was refluxed for 21 hours and the reaction mixture was allowed to stand at ambient temperature. The crystalline precipitates were collected by filtration, washed with toluene and recrystallized from tetrahydrofuran to give 4-hydroxy-N-(1-oxo-2,4,6cycloheptatrien-2-yl)-2H-thieno[2,3-e]-1,2-thiazine-3-carboxamide 1,1-dioxide (0.47 g). mp: 230 C. (dec.). IR (Nujol): 3260, 1550, 1500, 1450, 1400, 1340, 1180 cm-1 NMR (DMSO-d6, delta): 7.00-7.47 (5H, m), 7.57 (1H, d, J=5 Hz), 8.17 (1H, d, J=5 Hz), 8.89 (1H, d, J=9 Hz), 10.53 (1H, brs).

Reference£º
Patent; Fujisawa Pharmaceutical Co., Ltd.; US4563453; (1986); A;,
Thiazine – an overview | ScienceDirect Topics
Thiazine | C4H5NS – PubChem

A new synthetic route of Methyl 3-oxo-3,4-dihydro-2H-1,4-benzothiazine-6-carboxylate

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,188614-01-9,Methyl 3-oxo-3,4-dihydro-2H-1,4-benzothiazine-6-carboxylate,its application will become more common.

A common heterocyclic compound, 188614-01-9,Methyl 3-oxo-3,4-dihydro-2H-1,4-benzothiazine-6-carboxylate, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route. 188614-01-9

3-Oxo-3, 4-dihydro-2H-benzo [1, 4] thiazine-6-carboxylic acid methyl ester (6.74 g) was suspended in tetrahydrofuran (100 ml) and 2M sodium hydroxide [(30] ml) was added followed by water (20 ml). The solution was stirred for 2.5 hours, evaporated to half volume and acidified with 2M hydrochloric acid. The product was collected, washed with water and dried in vacuo, to give a white solid (6.2 g). MS (-ve ion electrospray) [L} L/Z] 208 (M-H)-

Reference£º
Patent; GLAXO GROUP LIMITED; WO2004/2992; (2004); A1;,
Thiazine – an overview | ScienceDirect Topics
Thiazine | C4H5NS – PubChem

A new synthetic route of 2-(Trifluoromethyl)-10H-phenothiazine

General procedure: In an air atmosphere, 2-phenylindole 1a (0.60 mmol), phenothiazine 2a (0.30 mmol),10mol% cuprous bromide and DMF (2mL) were added to the Schlenk reaction tube in sequence.In a constant temperature heating magnetic stirrer, the reaction was stirred at room temperature for 24 hours.After the reaction was completed, it was quenched with distilled water, extracted with ethyl acetate (3 ¡Á 20 mL), and the organic layers were combined.After drying over anhydrous sodium sulfate and spinning the organic phase, The crude product by column chromatography to give the pure product 3a (103.1 mg, 88%).

Reference£º
Patent; Henan Normal University; Zhao Peizheng; Wang Ke; Liu Jianming; Wang Zhixian; Shao Huibin; Yue Yuanyuan; (9 pag.)CN110407830; (2019); A;,
Thiazine – an overview | ScienceDirect Topics
Thiazine | C4H5NS – PubChem

Some scientific research about 3-Bromo-10H-phenothiazine

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,3939-23-9,3-Bromo-10H-phenothiazine,its application will become more common.

3939-23-9 A common heterocyclic compound, 3939-23-9,3-Bromo-10H-phenothiazine, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route.

2, under nitrogen protection will be prepared in step 1 p-phenylenediamine and phenothiazine derivatives according to 1:1 molar ratio was added to toluene, while adding potassium tert-butyl alcohol and palladium acetate as a catalyst,The reaction was heated to 80 C for 3 hours and then cooled to room temperature. The reaction was filtered,The filtrate was washed with dichloromethane and then the solvent was evaporated to dryness. The crude product was repeatedly washed with methanol and acetone,The product is obtained after purification by column chromatography., 3939-23-9

Reference£º
Patent; Changchun Hai Purunsi Technology Co., Ltd.; Guo Jianhua; (12 pag.)CN106831645; (2017); A;,
Thiazine – an overview | ScienceDirect Topics
Thiazine | C4H5NS – PubChem

The origin of a common compound about 92-30-8

General procedure: Formyl chloride derivatives (7 mmol) was added to the solution ofvarious arylamines (7 mmol) in acetone (25 ml). After stirring at 60 Cfor 6 h, the reaction mixture was concentrated to remove acetone. Theresidue was purified by column chromatography with petroleum/ethylacetate (9:1) to afford the target compound 15-27 and 29-32.

Reference£º
Article; Fu, Dong-Jun; Li, Miaomiao; Zhang, Sai-Yang; Li, Jiang-Feng; Sha, Beibei; Wang, Longhao; Zhang, Yan-Bing; Chen, Ping; Hu, Tao; Bioorganic Chemistry; vol. 92; (2019);,
Thiazine – an overview | ScienceDirect Topics
Thiazine | C4H5NS – PubChem

New downstream synthetic route of 37441-50-2

This compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,1,2-Thiazinane 1,1-dioxide,37441-50-2,its application will become more common.

A common heterocyclic compound, 37441-50-2,1,2-Thiazinane 1,1-dioxide, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc., below Introduce a new synthetic route. 37441-50-2

solution of 2-(3-chloro-4-fluorobenzyl)-8-ethyl-4-fluoro-10-methoxy-6-methyl-7,8- dihydropyrazino[l’,2′: 1,5]pyrrolo[2,3-d]pyridazine-1,9(2H,6H)-dione (0.10 g, 0.23 mmol; Example 139), 1,2-thiazinane 1,1-dioxide (45 mg, 0.33 mmol), and cesium carbonate (0.15 g, 0.46 mmol) in anhydrous DMSO (9.5 mL) was heated in an oil bath at 50 C for 5 hours. The product mixture was filtered through a pad of Celite and the filtrate was subjected to purification on reverse phase preparative HPLC purification. Collection and lyophilization of appropriate fractions afforded the title material. Analytical HPLC indicated that the product is a 1:1 mixture of two isomers that arose from the relative stereochemistry of the 6-methyl group and restricted rotation between the sultam ring and the tricyclic core. ?H NMR (400 MHz, CDCI3) No. 7.48 (m 1H), 7.28 (m, 1H), 7.11 (t, J = 8.5 Hz, 1H), 5.17 (d, J = 14.2 Hz, ?H), 5.34 (in, 1/2 H), 5.29 (d, J = 14.2 Hz, (at)H), 5.23 (d, J = 14.2 Hz, ?H), 5.09 (d, J = 14.2 Hz, ?H), 5.07 (m, ?H), 4.18 (s, 1.5H), 4.16 (s, 1.5H), 4.12-3.17 (m), 2.58-2.00 (m), 1.57 (d, J = 6.6 Hz, 1.5H), 1.42 (d, J = 6.8 Hz, 1.5H), 1.23 (t, J = 6.8 Hz, 1.5H), 1.22 (t, J = 7.1 Hz, 1.5H). ES MS M+1 = 552

Reference£º
Patent; MERCK & CO., INC.; WO2005/110414; (2005); A2;,
Thiazine – an overview | ScienceDirect Topics
Thiazine | C4H5NS – PubChem