Heterocyclic Building Blocks-benzodioxan

As a common heterocyclic compound, it belongs to benzodioxans compound, name is 1-(2,3-Dihydrobenzo[b][1,4]dioxin-6-yl)ethanone, and cas is 2879-20-1, its synthesis route is as follows.,2879-20-1

To a 38 mL pressure-resistant tube, 6-acetyl-1,4-benzodioxane (1.0 mmol), p-toluenesulfonylhydrazide (1.0 mmol), potassium thiocyanate (1.0 mmol), and iodine (2.0) were added. Methyl acetate (0.5 mmol) and 3 mL of DMSO, the mixture was stirred and heated at 130 C for 1 hour, and the reaction was monitored by thin layer chromatography (TLC) until the substrate was completely reacted and the product point was no longer changed. Stop the reaction.After the reaction was cooled to room temperature, it was poured into a saturated Na2S2O3(50 mL) solution, and extracted with EtOAc (50 mL*3). The organic phase was then poured into an Erlenmeyer flask and dried over anhydrous Na2SO4in the organic phase.After distilling off the solvent under reduced pressure, the crude product was purified by column chromatography eluting with petroleum ether and ethyl acetate to give a pale yellow solid. and the total yield 87%

With the complex challenges of chemical substances, we look forward to future research findings about 2879-20-1,belong benzodioxans compound

Reference£º
Patent; Central China Normal University; Wang Can; Geng Xiao; Wu Yandong; Wu Anxin; (11 pag.)CN110143930; (2019); A;,
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: C8H14ClNO200,mainly used in chemical industry, its synthesis route is as follows.,20197-75-5

To a solution of methyl 2,3-dihydrobenzo[6][l,4]dioxine-6-carboxylate (780 mg, 4.0 mmol) in acetic acid (3 mL) was added dropwise cone. HNO3 (4 mL) while keeping the temperature below 20 0 C and the resulting reaction mixture was warmed to room temperature. After stirring for 1 hr, the mixture was poured onto ice- water with vigorous stirring. The resulting white precipitate was collected by vacuum filtration and dried under reduced pressure to yield methyl 7-nitro-2,3-dihydrobenzo[6][l,4]dioxine-6- carboxylate (889 mg, 92percent). 1H NMR (DMSO-d6, 600 MHz) delta 7.64 (s, IH), 7.30 (s, IH), 4.41-4.38 (m, 4H), 3.80 (s, 3H); MS (ES+) m/z 240. 0 (M+H)+.

With the complex challenges of chemical substances, we look forward to future research findings about Methyl 1,4-Benzodioxan-6-carboxylate,belong benzodioxans compound

Reference£º
Patent; PRESIDENT AND FELLOWS OF HARVARD COLLEGE; WO2009/151561; (2009); A2;,
Benzodioxan
1,4-Benzodioxane | C8H8O2 – PubChem

As a common heterocyclic compound, it belongs to benzodioxans compound, name is 1-(2,3-Dihydrobenzo[b][1,4]dioxin-6-yl)ethanone, and cas is 2879-20-1, its synthesis route is as follows.,2879-20-1

General procedure: Carbonyl substrate, 0.02 mol, was added in portions to a suspension of 0.01 mol NaBH4 in 0.3 mol of the corresponding alcohol solvent, and the mixture was stirred for 2-2.5 h at 20C. The resulting boron derivatives of benzyl alcohols were decomposed with 10% aqueous HCl (3.7 mL), and the mixture was stirred for a required time at a required temperature(see Tables 1-5), cooled, and poured into 200 mL of cold water. The products were extracted with diethylether (2 ¡Á 40 mL), the combined extracts were washed with water and dried over anhydrous sodium sulfate, the solvent was distilled off on a rotary evaporator, and the residue was analyzed by 1H NMR. If necessary,benzyl ethers were isolated by chromatography. Alcohol coreactants poorly soluble in water were removed from the diethyl ether extracts by vacuum distillation, and the target ethers ware isolated from the still residue. Ethers 2a [9], 2c [3], 2h, 4a [10], 4b [11], 4i,4l, 7e, 10c, 10d, 10e [4], and 13a [12] were described previously. Ethers 2b, 2d-2g, 2i, 4c-4h, 4j, 4k, 4m-4w, 7a-7d, 7f, 7g, and 13b-13f are mobile liquids, and 7h-7j, 10a, 10b, and 10f-10i are viscous liquids.

With the complex challenges of chemical substances, we look forward to future research findings about 1-(2,3-Dihydrobenzo[b][1,4]dioxin-6-yl)ethanone

Reference£º
Review; Mochalov; Fedotov; Trofimova; Zefirov; Russian Journal of Organic Chemistry; vol. 52; 4; (2016); p. 503 – 512; Zh. Org. Khim.; vol. 52; 4; (2016); p. 503 – 512,10;,
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

Method I Ba (1 mmol) and 2,3-dihydrobenzo[b][1,4]dioxin-6-carboxylic acid (or 2,3-dihydrobenzo[b][1,4]dioxin-2-carboxylic acid) (1 mmol) together with EDCI (1.5 mmol) and HOBt (0.05 mmol) in CH2Cl2 (20 mL) were refluxed at room temperature for 10 h. While the reaction completed, the solution was washed with water for three times (30 mL each time). The remaining water layer was extracted by EtOAc for three times (30 mL each time). The organic layers (CH2Cl2 and EtOAc) were combined and then evaporated. The separated solid was crystallized from mixture of DMF and ethanol (9:1) to obtain the corresponding compound as translucent solid. 4.5.9 (2,3-Dihydrobenzo[b][1,4]dioxin-6-yl)(5-(4-fluorophenyl)-3-(4-methoxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl)methanone (C9) White crystal, yield mp: 236-237 ¡ãC. 1H NMR (CDCl3, 300 MHz) delta: 3.18-3.23(d, J = 16.8 Hz, 1H), 3.72-3.78 (m, 1H), 3.82 (s, 3H), 4.31-4.32 (t, J = 2.7 Hz, 4H), 5.72-5.78 (m, 1H), 7.04-7.11 (m, 5H), 7.22-7.25 (m, 2H), 7.43-7.49 (m, 1H), 7.58 (s, 1H), 7.74-7.76 (d, J = 7.2 Hz, 2H). MS (ESI): 433.15 (C25H22FN2O4, [M+H]+). Anal. Calcd for C25H21FN2O4: C, 69.44; H, 4.89; F, 4.39; N, 6.48; O, 14.80. Found: C, 69.08; H, 4.86; N, 6.49., 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; Yang, Yu-Shun; Li, Qing-Shan; Sun, Shuai; Zhang, Yan-Bin; Wang, Xiao-Liang; Zhang, Fei; Tang, Jian-Feng; Zhu, Hai-Liang; Bioorganic and Medicinal Chemistry; vol. 20; 20; (2012); p. 6048 – 6058;,
Benzodioxan
1,4-Benzodioxane | C8H8O2 – PubChem

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

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.

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

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

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

Oxalyl chloride (10 mL) is added to 2,3-dihydro-benzo[1 ,4]dioxine-6-carboxylic acid (14.9 g) dissolved in dichloromethane (100 mL). After the addition of N,N-dimethylformamide (0.5 ml_), the mixture is stirred at room temperature overnight and then concentrated. The residue is taken up in dichloromethane (100 ml.) and added to a mixture of nortropinone hydrochloride (10.0 g) and potassium carbonate (12.0 g) in dichloromethane (50 ml_). Then, pyridine (18 ml.) is added and the mixture is stirred at room temperature overnight. The mixture is concentrated and the residue is taken up in dichloromethane and washed with 1 M aqueous hydrochloric acid, 1 M aqueous NaOH solution, and brine. After drying (Na2SO4), the solvent is removed under reduced pressure to yield the title compound. Yield: 17.3 g (75percent of theory) Mass spectrum (ESI+): m/z = 288 [M+H]+

As the rapid development of chemical substances, we look forward to future research findings about 4442-54-0

Reference£º
Patent; BOEHRINGER INGELHEIM INTERNATIONAL GMBH; ECKHARDT, Matthias; HAMILTON, Bradford, S.; HIMMELSBACH, Frank; PETERS, Stefan; WO2010/23161; (2010); A1;,
Benzodioxan
1,4-Benzodioxane | C8H8O2 – PubChem

A common heterocyclic compound, the benzodioxans compound, name is 2,3-Dihydro-1,4-benzodioxine-6-carboxylic acid,cas is 4442-54-0, mainly used in chemical industry, its synthesis route is as follows.,4442-54-0

EXAMPLE 120 2,3-Dihydro-benzo[1,4]dioxine-6-carboxylic acid methyl ester A solution of 19.6 g (109 mmol) of 2,3-dihydro-benzo[1,4]dioxine-6-carboxylic acid (J. Chem. Soc., 3445, 1957) in 400 mL of MeOH containing 4 mL of H2SO4 was refluxed overnight. Sodium bicarbonate (18 g) was added, the solvent was removed and the residue was triturated several times with Et2O. The washes were combined, filtered through anhyd MgSO4 and evaporated to yield 20.7 g of the title compound as a pale yellow oil: mass spectrum (electron impact, m/e): 194.

As the rapid development of chemical substances, we look forward to future research findings about 4442-54-0

Reference£º
Patent; American Cyanamid Company; US6288082; (2001); B1;,
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

Method I Ba (1 mmol) and 2,3-dihydrobenzo[b][1,4]dioxin-6-carboxylic acid (or 2,3-dihydrobenzo[b][1,4]dioxin-2-carboxylic acid) (1 mmol) together with EDCI (1.5 mmol) and HOBt (0.05 mmol) in CH2Cl2 (20 mL) were refluxed at room temperature for 10 h. While the reaction completed, the solution was washed with water for three times (30 mL each time). The remaining water layer was extracted by EtOAc for three times (30 mL each time). The organic layers (CH2Cl2 and EtOAc) were combined and then evaporated. The separated solid was crystallized from mixture of DMF and ethanol (9:1) to obtain the corresponding compound as translucent solid. 4.5.7 (2,3-Dihydrobenzo[b][1,4]dioxin-6-yl)(5-(4-fluorophenyl)-3-phenyl-4,5-dihydro-1H-pyrazol-1-yl)methanone (C7) White crystal, mp: 137-138 ¡ãC. 1H NMR (CDCl3, 300 MHz) delta: 3.20-3.26 (d, J = 17.4 Hz, 1H), 3.76-3.81 (m, 1H), 4.33-4.34 (t, J = 2.1 Hz, 4H), 5.76-5.82 (m, 1H), 7.05-7.12 (m, 3H), 7.25-7.28 (m, 2H), 7.45-7.51 (m, 4H), 7.59 (s, 1H), 7.65-7.68 (d, J = 8.1 Hz, 2H). MS (ESI): 403.14 (C24H20FN2O3, [M+H]+). Anal. Calcd for C24H19FN2O3: C, 71.63; H, 4.76; F, 4.72; N, 6.96; O, 11.93. Found: C, 71.31; H, 4.75; N, 6.97.

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; Yang, Yu-Shun; Li, Qing-Shan; Sun, Shuai; Zhang, Yan-Bin; Wang, Xiao-Liang; Zhang, Fei; Tang, Jian-Feng; Zhu, Hai-Liang; Bioorganic and Medicinal Chemistry; vol. 20; 20; (2012); p. 6048 – 6058;,
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.

General procedure: A mixture of commercial carboxylic acid in freshly distilled thionyl chloride is warmed into reflux for 2 h, then cooled to room temperature and evaporated under vacuum to dryness to afford quantitatively corresponding acid chlorides (3). This crude material might be used without further purification. A mixture of these acid chloride (1.0 equiv) and ammonium thiocyanate (1.0 equiv) is heated in refluxing dry acetone for 1h. Then, the mixture is cooled to room temperature, and a solution of benzimidazole in dry acetone is carefully added. The mixture is warmed again for 1 h, then cooled to 0 ¡ãC, and hydrolyzed with ice. The precipitate is washed with cold water and crude material is crystallized into ethanol., 4442-54-0

As the paragraph descriping shows that 4442-54-0 is playing an increasingly important role.

Reference£º
Article; Liu, Wang-Qing; Megale, Valentino; Borriello, Lucia; Leforban, Bertrand; Montes, Matthieu; Goldwaser, Elodie; Gresh, Nohad; Piquemal, Jean-Philip; Hadj-Slimane, Reda; Hermine, Olivier; Garbay, Christiane; Raynaud, Francoise; Lepelletier, Yves; Demange, Luc; Bioorganic and Medicinal Chemistry Letters; vol. 24; 17; (2014); p. 4254 – 4259;,
Benzodioxan
1,4-Benzodioxane | C8H8O2 – PubChem

3663-80-7, 2,3-Dihydrobenzo[b][1,4]dioxine-2-carboxylic acid is a benzodioxans compound, ?involved in a variety of chemical synthesis. Rlated chemical reaction is continuously updated

Example 27 d6-[4-(4-Amino-6,7-dimethoxy-quinazolin-2-yl)-piperazin-1-yl]-(2,3-dihydro-benzo1,4]dioxin-2-yl)-methanone hydrochloride salt A mixture of 1,4-benzodioxane-6-carboxylic acid (901 mg, 5 mmol), piperazine (431 mg, 5 mmol) and hexamethyldisilazane (1.61 g, 10 mmol) was heated to 110¡ã C. for 15 hours. The reaction was cooled, concentrated, and purified by column chromatography to yield 2,3-dihydro-benzo[1,4]dioxin-2-yl)-piperazin-1-yl-methanone (400 mg, 32percent). 1H NMR (300 MHz, CDCl3) delta 6.94-6.85 (m, 4H), 4.84 (dd, J=8.1, 2.4 Hz, 1H), 4.52 (dd, J=12.0, 2.4 Hz, 1H), 4.330 (dd, J=12.0, 8.1 Hz, 1H), 3.75 (m, 2H), 3.56 (m, 2H), 2.99-2.91 (m, 4H); ESI-MS m/z 249 (M+H)., 3663-80-7

3663-80-7 2,3-Dihydrobenzo[b][1,4]dioxine-2-carboxylic acid 2735450, abenzodioxans compound, is more and more widely used in various fields.

Reference£º
Patent; AUSPEX PHARMACEUTICALS, INC.; US2008/39473; (2008); A1;,
Benzodioxan
1,4-Benzodioxane | C8H8O2 – PubChem