Heterocyclic Building Blocks-benzodioxan

As a common heterocyclic compound, it belong benzodioxans compound,2,3-Dihydro-1,4-benzodioxine-6-carboxylic acid,4442-54-0,Molecular formula: C9H8O4,mainly used in chemical industry, its synthesis route is as follows.,4442-54-0

Preparation of Compound 122, N-(3-Nitrophenyl)-2,3-dihydro-1,4-benzodioxine-7-carboxamide[00148] 2,3-Dihydrobenzo[b][1,4]dioxine-6-carboxylic acid (3.13 g, 17.38 mmol) was dissoved in DMA (25 mL) and (7.57 ml_, 43.44 mmol) and HATU (6.61 g, 17.38 mmol) added under an inert atmosphere. The reaction was allowed to stir for 15 minutes then 3-nitroaniline (2.0 g, 14.48 mmol) was added and the reaction stirred at ambient temperature overnight. The reaction was heated for a further 16 hours at 40 ¡ãC then concentrated in vacuo and water added. The solids were isolated by filtration, washed with wate and dried in a vacuum oven. The solids were stirred in EtOAc for an hour and then filtered. The filtrate was evaporated down and the solids were triturated with DCM then filtered. The collected solids were combined to afford the desired material as a cream solid (3.44 g, 79percent).1H NMR (400 MHz, DMSO, 30¡ãC) d 4.33 (4H, tq), 7.03 (1 H, d), 7.53 – 7.59 (2H, m), 7.65 (1 H, t), 7.95 (1 H, ddd), 8.20 (1 H, ddd), 8.78 – 8.82 (1 H, m), 10.48 (1 H, s). m/z (ES+) (M+H)+ = 301 .

With the synthetic route has been constantly updated, we look forward to future research findings about 2,3-Dihydro-1,4-benzodioxine-6-carboxylic acid,belong benzodioxans compound

Reference£º
Patent; CANCER RESEARCH TECHNOLOGY LIMITED; JONES, Keith; RYE, Carl; CHESSUM, Nicola; CHEESEMAN, Matthew; PASQUA, Adele Elisa; PIKE, Kurt Gordon; FAULDER, Paul Frank; WO2015/49535; (2015); A1;,
Benzodioxan
1,4-Benzodioxane | C8H8O2 – PubChem

Name is 2,3-Dihydrobenzo[b][1,4]dioxine-2-carboxylic acid, as a common heterocyclic compound, it belongs to benzodioxans compound, and cas is 3663-80-7, its synthesis route is as follows.,3663-80-7

To a solution of Example 23B (40mg, 0.140 mmol) in N,N-dimethylformamide (0.8 mL) were added 2,3-dihydrobenzo[Z?][l ,4]dioxine-2-carboxylic acid (27.8 mg, 0.155 mmol), 1- [bis(dimethylamino)methylene]- lH-l,2,3-triazolo[4,5- ?]pyridinium 3-oxid hexafluorophosphate (HATU, 58.8 mg, 0.155 mmol), and NN-diisopropylethylamine (0.074 mL, 0.421 mmol) at room temperature. The reaction mixture was stirred for 1 hour at room temperature. The mixture was purified by preparative HPLC [Waters XB ridge? C18 5 muiotaeta OBD? column, 30 x 100 mm, flow rate 40 mL/minute, 5-100percent gradient of acetonitrile in buffer (0.1 percent trifluoroacetic acid in water)] to give the title compound.(45mg, 0.101 mmol, 71.7 percent yield). H NMR (501 MHz, DMSO-ifc) delta ppm 8.78 (s, 1H), 8.70 (s, 1H), 7.47 (t, J = 8.9 Hz, 1H), 7.05 (dd, J = 11.3, 2.9 Hz, 1H), 6.97 – 6.92 (m, 1H), 6.87 – 6.80 (m, 4H), 4.67 (dd, J = 6.5, 2.7 Hz, 1H), 4.45 (s, 2H), 4.31 (dd, J = 11.6, 2.7 Hz, 1H), 4.12 (dd, J = 11.6, 6.5 Hz, 1H), 2.24 (s, 6H); MS (ESI+) m/z 464 (M+NH4)+.

With the complex challenges of chemical substances, we look forward to future research findings about 2,3-Dihydrobenzo[b][1,4]dioxine-2-carboxylic acid

Reference£º
Patent; CALICO LIFE SCIENCES LLC; ABBVIE INC.; MARTIN, Kathleen, Ann; SIDRAUSKI, Carmela; FROST, Jennifer, M.; TONG, Yunsong; XU, Xiangdong; CHUNG, Seungwon; ZHANG, Qingwei, I.; SHI, Lei; MURAUSKI, Kathleen; DART, Michael, J.; RANDOLPH, John, T.; (238 pag.)WO2019/90085; (2019); A1;,
Benzodioxan
1,4-Benzodioxane | C8H8O2 – PubChem

2,3-Dihydrobenzo[b][1,4]dioxine-2-carboxylic acid, cas is 3663-80-7, it is a common heterocyclic compound, the benzodioxans compound, its synthesis route is as follows.

To a solution of Example 24A (64 mg, 0.140 mmol) in N,N-dimethylformamide (0.8 mL) were added 2,3-dihydrobenzo[Z?][l,4]dioxine-2-carboxylic acid (27.8 mg, 0.154 mmol), 1- [bis(dimethylamino)methylene]-lH-l,2,3-triazolo[4,5-/?]pyridinium 3-oxid hexafluorophosphate (HATU, 58.6 mg, 0.154 mmol), and N.N-diisopropylethylamine (0.073 mL, 0.420 mmol) at room temperature. The reaction mixture was stirred 1 hour at room temperature. The mixture was purified by preparative HPLC [Waters XB ridge? C18 5 muiotaeta OBD? column, 30 x 100 mm, flow rate 40 mL/minute, 5-100percent gradient of acetonitrile in buffer (0.1percent trifluoroacetic acid in water)] to give the title compound. (25 mg, 0.05 mmol, 35.3 percent yield). lH NMR (400 MHz, DMSO- ) delta ppm 7.47 (s, 1H), 7.44 (t, J = 8.9 Hz, 1H), 7.21 (d, J = 7.6 Hz, 1H), 6.98 (dd, J = 11.4, 2.9 Hz, 1H), 6.94 – 6.88 (m, 1H), 6.86 – 6.79 (m, 3H), 6.77 (ddd, J = 9.0, 2.9, 1.2 Hz, 1H), 4.65 (dt, J = 6.5, 3.1 Hz, 1H), 4.39 (s, 2H), 4.29 (dt, J = 11.5, 3.0 Hz, 1H), 4.09 (ddd, J = 11.6, 6.6, 3.3 Hz, 1H), 3.92 (ddd, J = 39.3, 9.5, 3.2 Hz, 1H), 2.24 (tdd, J = 12.3, 9.5, 2.5 Hz, 1H), 2.13 (ddt, J = 17.7, 7.6, 3.0 Hz, 1H), 1.95 – 1.64 (m, 8H); MS (ESI+) m/z 522 (M+H)+., 3663-80-7

With the rapid development of chemical substances, we look forward to future research findings about 2,3-Dihydrobenzo[b][1,4]dioxine-2-carboxylic acid

Reference£º
Patent; CALICO LIFE SCIENCES LLC; ABBVIE INC.; MARTIN, Kathleen, Ann; SIDRAUSKI, Carmela; FROST, Jennifer, M.; TONG, Yunsong; XU, Xiangdong; CHUNG, Seungwon; ZHANG, Qingwei, I.; SHI, Lei; MURAUSKI, Kathleen; DART, Michael, J.; RANDOLPH, John, T.; (238 pag.)WO2019/90085; (2019); A1;,
Benzodioxan
1,4-Benzodioxane | C8H8O2 – PubChem

(2,3-Dihydrobenzo[b][1,4]dioxin-5-yl)methanol, cas is 274910-19-9, it is a common heterocyclic compound, the benzodioxans compound, its synthesis route is as follows.,274910-19-9

A solution of 20 (3.75 g, 32.3 mmol) in diethyl ether (80 mL) was cooled to 0 C and phosphorous tribromide (3.67 mL, 38.8 mmol) was added dropwise. The solution was stirred at 0 C for 10 min, then at r.t. for 1 h. Water (10 mL) was added cautiously to quench the excess of reagent and the mixture was diluted with diethyl ether and washed with water (3 x 50 mL). The combined organic layers were washed with brine (100 mL), dried over Na2S04, filtered and concentrated under reduced pressure to obtain 21 as a brown solid (4.61 g, 62%). 1H NMR (CDCI3) delta 6.91-6.77 (m, 3H), 4.52 (s, 2H), 4.35-4.33 (m, 2H), 4.29-4.27 (m, 2H). Found: [M+H- Br]=149.5.

274910-19-9 is used more and more widely, we look forward to future research findings about (2,3-Dihydrobenzo[b][1,4]dioxin-5-yl)methanol

Reference£º
Patent; THE GLOBAL ALLIANCE FOR TB DRUG DEVELOPMENT, INC.; UPTON, Anna, Marie; COOPER, Christopher, Blair; MARCEL, Koenraad, Jozel Lodewijk; GUILLEMONT, Jerome, Emile Goerges; VAN DEN BROECK, Walter Marcel, Mathilde; PALMER, Brian, Desmond; MA, Zhenkun; (186 pag.)WO2017/155909; (2017); A1;,
Benzodioxan
1,4-Benzodioxane | C8H8O2 – PubChem

4442-54-0, 2,3-Dihydro-1,4-benzodioxine-6-carboxylic acid is a benzodioxans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

General procedure: To a mixture of compound 7 (0.05 g, 0.17 mmol) and the appropriate aromatic carboxylic acid (0.34 mmol) in anhydrous DMF (2 mL) under argon atmosphere, N,N-diisoprpoylethylamine (DIPEA) (0.128 mL, 0.72 mmol) and HATU (0.168 g, 0.442 mmol)were added. The reaction mixture was stirred at rt for 24 h or at 80 ¡ãC for 5 h (for only 8g), and then quenched with water (30 mL).The aqueous layer was extracted with ethyl acetate (3 20 mL) and the combined organic layers were washed with water and brine,dried over anhydrous Na2SO4, filtered, and the solvent wasremoved under reduced pressure. The resultant residue was purified by flash column chromatography, using the appropriate elution system to afford the target compounds 8a-g in pure form. 4.9.7 4-((2-(2,3-Dihydrobenzo[b][1,4]dioxine-6-carboxamido)quinolin-5-yl)oxy)-N-methylpicolinamide (8g) Flash column chromatography was performed using (hexane:ethyl acetate, 2:1 to 1:1 v/v). White solid; yield 35.7percent; mp 107-110 ¡ãC; 1H NMR (300 MHz, CDCl3) delta 8.81 (br. s, 1H), 8.55 (d, J = 9.2 Hz, 1H), 8.42 (d, J = 5.6 Hz, 1H), 8.28 (d, J = 9.3 Hz, 1H), 8.01 (d, J = 4.4 Hz, 1H), 7.75-7.75 (m, 2H), 7.66 (t, J = 7.6 Hz, 1H), 7.55 (d, J = 2.1 Hz, 1H), 7.49 (dd, J = 8.4, 2.2 Hz, 1H), 7.13 (dd, J = 7.5, 0.8 Hz, 1H), 7.01 (dd, J = 5.6, 2.6 Hz, 1H), 6.97 (d, J = 8.4 Hz, 1H), 4.33 (d, J = 2.6 Hz, 4H), 3.01 (d, J = 5.1 Hz, 3H); 13C NMR (75 MHz, CDCl3) delta 166.34, 165.23, 164.40, 152.61, 152.05, 149.98, 149.41, 148.14, 147.50, 143.72, 132.75, 129.90, 127.10, 125.19, 120.90, 120.15, 117.59, 117.12, 115.61, 114.91, 114.15, 110.35, 64.65, 64.21, 26.16.

4442-54-0, 4442-54-0 2,3-Dihydro-1,4-benzodioxine-6-carboxylic acid 2758833, abenzodioxans compound, is more and more widely used in various fields.

Reference£º
Article; El-Damasy, Ashraf Kareem; Seo, Seon Hee; Cho, Nam-Chul; Kang, Soon Bang; Pae, Ae Nim; Kim, Key-Sun; Keum, Gyochang; European Journal of Medicinal Chemistry; vol. 101; (2015); p. 754 – 768;,
Benzodioxan
1,4-Benzodioxane | C8H8O2 – PubChem

As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO307,mainly used in chemical industry, its synthesis route is as follows.,17413-10-4

Step 1..Preparation of 3-((2,3-dihydrobenzo[b][1 ,4]dioxin-6-yl)methyl)-2-imidazolidin-4- one; A suspension of (2,3-Dihydro-benzo[1 ,4]dioxin-6-yl)-methylamine (16.5 mmol, 2.73 g) in 1 MNaOH is refluxed for 10 min and cooled to room temperature. Subsequently bis(carboxymethyl) trithiocarbonate (3.74 g, 16.5 mmol) is added and the reaction mixture refluxed overnight to give the precipitate, which is filtered off and is washed with water (3x 20 ml_). The remaining residue is suspended in a mixture of methanol and isopropanol (1 :1 , 25 ml_) and refluxed for 10 minutes. Cooled reaction mixture is filtered and the solid residue dried at lower temperature and recrystallyzed from methanol to give 3.29 g of 3-((2,3- dihydrobenzo[b][1 ,4]dioxin-6-yl)methyl)-imidazolidin-2,4-dione.

With the synthetic route has been constantly updated, we look forward to future research findings about (2,3-Dihydrobenzo[b][1,4]dioxin-6-yl)methanamine,belong benzodioxans compound

Reference£º
Patent; LEK PHARMACEUTICAL D.D.; WO2008/43733; (2008); A1;,
Benzodioxan
1,4-Benzodioxane | C8H8O2 – PubChem

As a common heterocyclic compound, it belongs to benzodioxans compound, name is (2,3-Dihydrobenzo[b][1,4]dioxin-5-yl)methanol, and cas is 274910-19-9, its synthesis route is as follows.,274910-19-9

A solution of 2,3-dihydro-1,4-benzodioxin-5-ylmethanol (Intermediate A1) (commercially available from Aldrich) (3 g, 18.1 mmol) in THF (100 mL) was treated with manganese(IV) oxide, activated (commercially available from Aldrich): MnO2 (10 g, 115 mmol) at rt. The mixture was heated to 35 C. for 2 h and 60 C. for 4 h followed by 18 h at room temperature (rt). The mixture was filtered through celite and the solvent was removed under vacuum. The residue was purified by chromatography on silica gel with 20% EtOAc:hexanes to give 2,3-dihydro-benzo[1,4]dioxine-5-carbaldehyde (Intermediate A2) 2.6 g (88%). A mixture of 4-iodo-1-tritylimidazole (commercially available) (8.64 g, 19.8 mmol) in dichloromethane (100 mL) at -10 C. was treated with ethyl magnesium bromide (6.3 mL, 19 mmol, 3M in THF) and allowed to react for 45 m. A solution of 2,3-dihydro-benzo[1,4]dioxine-5-carbaldehyde (Intermediate A2) (2.6 g, 15.9 mmol) in dichloromethane was added via syringe at -10 C. and stirred for 45 m. The mixture was quenched with water (50 mL) and a sat. solution of ammonium chloride (50 mL). The residue was isolated in a typical aqueous workup and purified by chromatography on silica gel with 3 to 5% NH3-MeOH:CH2Cl2 to give (2,3-dihydro-benzo[1,4]dioxin-5-yl)-(1-trityl-1H-imidazol-4-yl)-methanol (Intermediate A3) as a solid, 2.9 g (40%). A solution of (2,3-dihydro-benzo[1,4]dioxin-5-yl)-(1-trityl-1H-imidazol-4-yl)-methanol (Intermediate A3) (1 g, 2.11 mmol) in dichloromethane (30 mL) was reacted with TFA:trifluoroacetic acid (5.3 mL, 68 mmol)) and triethylsilane (TES) (2.8 mL, 17 mmol) at rt for 24 h. The mixture was evaporated under reduced pressure and quenched with solid NaHCO3. This material was subjected to an aqueous work-up and the residue was purified by chromatography on silica gel with 5% NH3-MeOH:CH2Cl2 to yield 5-(2,3-dihydro-benzo[1,4]dioxin-5-ylmethyl)-1H-imidazole (Intermediate A4) 330 mg (72%). A mixture of 5-(2,3-dihydro-benzo[1,4]dioxin-5-ylmethyl)-1H-imidazole (Intermediate A4) (260 mg, 1.2 mmol) in THF (10 mL) and water (10 mL) was treated with NaHCO3 (1 g, 12 mmol) and phenylchlorothionoformate (0.42 mL, 3.13 mmol) for 3 h at rt. The mixture was diluted with diethyl ether (35 mL) and water (10 mL). The aqueous layer was removed and extracted with ether (2¡Á10 mL). The organic layers were combined, dried over MgSO4, filtered and concentrated under vacuum. The residue was treated with triethylamine (1 mL) in methanol (9 mL) at rt for 16 h. The solvent was removed and the product was isolated and purified either by tituration with CH2Cl2:hexane or by chromatography on SiO2 with EtOAc or 3% MeOH:CH2Cl2. This gave 4-(2,3-dihydro-benzo[1,4]dioxin-5-ylmethyl)-1,3-dihydro-imidazole-2-thione (Compound-1) 150 mg (50%). 1H NMR (300 MHz, DMSO-d6 w/TMS): delta 11.9 (brs, 1H), 11.7 (s, 1H), 6.76-6.65 (m, 3H), 6.41 (s, 1H), 4.28-4.21 (m, 4H), 3.61 (s, 2H).

With the complex challenges of chemical substances, we look forward to future research findings about 274910-19-9,belong benzodioxans compound

Reference£º
Patent; Allergan, Inc.; US2006/69144; (2006); A1;,
Benzodioxan
1,4-Benzodioxane | C8H8O2 – PubChem

Name is 2,3-Dihydro-1,4-benzodioxine-6-carboxylic acid, as a common heterocyclic compound, it belongs to benzodioxans compound, and cas is 4442-54-0, its synthesis route is as follows.,4442-54-0

1, 4 – benzene and dioxane -6 – formic acid (25.0g, 139mmol) dissolved in methanol (180 ml) in, concentrated sulfuric (17.5 ml), heated to 70 ¡ãC stirring 5 hours. Cooling to room temperature, concentrated under reduced pressure, for 5percent of sodium hydroxide aqueous solution to adjust the pH to the alkaline, extracted with ethyl acetate, dried, concentrated to obtain 1, 4 – benzene and dioxane -6 – methyl formate (white solid 26.8g, 99percent).

With the complex challenges of chemical substances, we look forward to future research findings about 2,3-Dihydro-1,4-benzodioxine-6-carboxylic acid

Reference£º
Patent; Shanghai Huilun Life Technology Co., Ltd.; Cheng Jianjun; Qin Jihong; (25 pag.)CN104557955; (2017); B;,
Benzodioxan
1,4-Benzodioxane | C8H8O2 – PubChem

With the rapid development and complex challenges of chemical substances, new drug synthesis pathways are usually the most effective.4442-54-0,2,3-Dihydro-1,4-benzodioxine-6-carboxylic acid,as a common compound, the synthetic route is as follows.

2,3-Dihydrobenzo[b][1,4]dioxine-6-carboxylic acid (1 mmol) in methanol (30 ml) was treated with concentrated sulfuric acid (0.5 ml) under reflux overnight. The sovlent was removed in vacuo leaving oil which was dissovled in ethyl acetate (20 ml) and extracted with water (40 ml). After drying the organic layer with anhydrous Na2SO4 and evaporating the solvent under reduced pressure and a solid appeared. The solid was recyrstallized from ethanol to obtain the compound 1., 4442-54-0

The synthetic route of 4442-54-0 has been constantly updated, and we look forward to future research findings.

Reference£º
Article; Hou, Ya-Ping; Sun, Juan; Pang, Zhong-Hua; Lv, Peng-Cheng; Li, Dong-Dong; Yan, Li; Zhang, Hong-Jia; Zheng, Emily Xi; Zhao, Jing; Zhu, Hai-Liang; Bioorganic and Medicinal Chemistry; vol. 19; 20; (2011); p. 5948 – 5954;,
Benzodioxan
1,4-Benzodioxane | C8H8O2 – PubChem

2,3-Dihydrobenzo[b][1,4]dioxine-5-carboxylic acid, cas is 4442-53-9, it is a common heterocyclic compound, the benzodioxans compound, its synthesis route is as follows.,4442-53-9

4.1.1.1. 6-Bromo-3-((2,3-dihydrobenzo[b][1,4]dioxin-5-yl)methyl)-2-methoxyquinoline (VI: Y = 2,3-O(CH2)2O-). To a solution of 2,3-dihydrobenzo[b][1,4]dioxine-5-carboxylic acid (5.00 g, 28.0 mmol)in THF (150 mL) at 0 C was added lithium aluminium hydride(2.13 g, 56.0 mmol) in small portions. The reaction mixture wasstirred at 0 C for 10 min and stirred for a further 18 h at 20 C.Water (150 mL) was added to the reaction mixture which wasextracted with EtOAc (2 100 mL). The combined organic layerswere washed with brine (100 mL), dried over Na2SO4, filteredand concentrated under reduced pressure to obtain (2,3-dihydrobenzo[b][1,4]dioxin-5-yl)methanol as a yellow oil (3.22 g,99%). 1H NMR (CDCl3, 400 MHz) d 6.87-6.79 (m, 3H), 4.66 (s, 2H),4.32-4.30 (m, 2H), 4.28-4.25 (m, 2H), 2.19 (bs, 1H). Found: [M+H-18] = 149.5.

With the rapid development of chemical substances, we look forward to future research findings about 2,3-Dihydrobenzo[b][1,4]dioxine-5-carboxylic acid

Reference£º
Article; Sutherland, Hamish S.; Tong, Amy S.T.; Choi, Peter J.; Conole, Daniel; Blaser, Adrian; Franzblau, Scott G.; Cooper, Christopher B.; Upton, Anna M.; Lotlikar, Manisha U.; Denny, William A.; Palmer, Brian D.; Bioorganic and Medicinal Chemistry; vol. 26; 8; (2018); p. 1797 – 1809;,
Benzodioxan
1,4-Benzodioxane | C8H8O2 – PubChem