Name: 271-58-9|Benzo[c]isoxazole|98%
Brand: Ambeed
SKU: A550798
Price: 6.0 USD
Availability: InStock
Rating: 98 (30 reviews)

1
[ 271-58-9 ]
[ 77-78-1 ]
[ 7755-70-6 ]

Reference： [1]Chemische Berichte,1904,vol. 37,p. 967,973, 979
Chemische Berichte,1909,vol. 42,p. 1648 Anm. 6

2
[ 552-89-6 ]
[ 271-58-9 ]

Yield	Reaction Conditions	Operation in experiment
88%	With vasicine; In ethylene glycol; at 80℃; for 48.0h;	General procedure: The mixture of nitrocompound (0.5 mmol) and vasicine (0.5 mmol) in ethylene glycol (2 mL) was stirred at 80C for 24-48 h. Time was not optimized separately for all substrates. After completion of reaction as monitored by TLC, the reaction mixture was cooled to ambient temperature and extracted with ethyl acetate. The ethyl acetate layer was dried under reduced pressure using rotatory evaporator. The crude was chromatographed over silica gel to afford the desired product.
86%	With tin(II) chloride dihdyrate; In methanol; ethyl acetate; at 25℃; for 20.0h;	General procedure: A round bottom flask equipped with a magnetic stirrer bar was charged with the 2-nitroacylbenzene (1.00 mmol) in EtOAc-MeOH (1:1; 5 mL). SnCl2.H2O (3.00 mmol) was added and the reaction stirred at room temperature overnight. The reaction was partitioned between DCM (30 mL) and NaHCO3 (20 mL). The aqueous phase was extracted with DCM (3 × 10 mL) and the organic portions combined, washed with H2O (10 mL), saturated aqueous NaCl (10 mL), dried over MgSO4, filtered and reduced in vacuo. The residue was purified by column chromatography (SiO2, hexane/EtOAc) to provide the title compound. General procedure gave the title compound as a yellow oil (102 mg, 86 %).

Reference： [1]ACS Catalysis,2017,vol. 7,p. 8255 - 8262
[2]Organic and Biomolecular Chemistry,2019,vol. 17,p. 5902 - 5907
[3]Tetrahedron Letters,2000,vol. 41,p. 2137 - 2140
[4]Angewandte Chemie - International Edition,2017,vol. 56,p. 12736 - 12740
    Angew. Chem.,2017,vol. 129,p. 12910 - 12914,5
[5]Chemistry - A European Journal,2019,vol. 25,p. 5288 - 5297
[6]Tetrahedron Letters,2016,vol. 57,p. 5003 - 5008
[7]Tetrahedron Letters,2012,vol. 53,p. 4951 - 4954
[8]Chemical Communications,2019,vol. 55,p. 12255 - 12258
[9]Organic Mass Spectrometry,1984,vol. 19,p. 306 - 310
[10]Journal of Organic Chemistry,1994,vol. 59,p. 3375 - 3380
[11]Chemische Berichte,1882,vol. 15,p. 2105
[12]Chemische Berichte,1882,vol. 15,p. 2105
[13]Chemische Berichte,1882,vol. 15,p. 2105
[14]Journal of the Society of Chemical Industry,1926,vol. 45,p. 93 T
    Chemisches Zentralblatt,1926,vol. 97,p. 193
[15]Chemische Berichte,1903,vol. 36,p. 3653
[16]Annali di Chimica Applicata,vol. 12,p. 128
    Chemisches Zentralblatt,1920,vol. 91,p. 338
[17]Heterocycles,1998,vol. 48,p. 749 - 754
[18]Heterocycles,1998,vol. 48,p. 2581 - 2592
[19]Heterocycles,1999,vol. 51,p. 1921 - 1928
[20]Heterocycles,1999,vol. 51,p. 1921 - 1928
[21]Angewandte Chemie - International Edition,2016,vol. 55,p. 794 - 797
    Angew. Chem.,2016,vol. 128,p. 804 - 808,5
[22]European Journal of Organic Chemistry,2017,vol. 2017,p. 3699 - 3706
[23]Organic Letters,2018,vol. 20,p. 2204 - 2207
[24]Angewandte Chemie - International Edition,2018,vol. 57,p. 16549 - 16553
    Angew. Chem.,2018,vol. 130,p. 16787 - 16791,5
[25]Chemistry - A European Journal,2019,vol. 25,p. 3000 - 3004
[26]Chemical Communications,2019,vol. 55,p. 9007 - 9010
[27]Chemical Communications,2019,vol. 55,p. 12072 - 12075
[28]Organic Letters,2020,vol. 22,p. 1504 - 1509
[29]Green Chemistry,2020,vol. 22,p. 3820 - 3826
[30]Organic Letters,2020

3
[ 271-58-9 ]
[ 917-54-4 ]
[ 7755-70-6 ]

Reference： [1]Organic and Biomolecular Chemistry,2005,vol. 3,p. 4351 - 4361
[2]Angewandte Chemie - International Edition,2013,vol. 52,p. 13280 - 13283
Angew. Chem.,2013,vol. 125,p. 13522 - 13525,4
[3]Journal of Organic Chemistry,1987,vol. 52,p. 2983 - 2988

4
[ 271-58-9 ]
[ 591-51-5 ]
[ 95888-33-8 ]

Reference： [1]Organic and Biomolecular Chemistry,2005,vol. 3,p. 4351 - 4361
[2]Journal of Organic Chemistry,1987,vol. 52,p. 2983 - 2988

5
[ 17064-77-6 ]
[ 271-58-9 ]

Reference： [1]Tetrahedron Letters,2000,vol. 41,p. 2137 - 2140
[2]Heterocycles,1998,vol. 48,p. 2581 - 2592
[3]Heterocycles,1999,vol. 51,p. 1921 - 1928

6
[ 271-58-9 ]
[ 253-82-7 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; sodium hydroxide; ammonia; In water;	To 1.25 g (4.6 mmol) of the anthranil (15), in a dried round bottom flask equipped with a dry ice condenser, was condensed approximately 50 ml of anhydrous NH3. The mixture was magnetically stirred for 40 min. At this time, the dry ice condenser was removed, and the NH3 was allowed to evaporate. Upon evaporation, 15 ml water and 1.5 ml of 2N NaOH were added, and the solution was refluxed for 1 hr. The solution was then cooled to room temperature, and 1N HCl was added adjusting the pH to approximately 9 and thus precipitating the quinazoline. The white substance was filtered off, washed with water and dried, yielding 0.71 g (57%). M.P. 273-274 C. IR (KBr) 3189, 3074, 2990, 2974, 2899, 2362, 1676, 1643, 1552, 1461, 1303, 1286, 1063, 872, 832 cm-1; 1 H NMR (CDCl3) delta2.39 (s, 3H), 3.98 (s, 3H), 7.39 (d, 1H, J=9.0 Hz), 7.59 (d, 1H, J=9.0 Hz), 11.60 (s, 1H), Anal. Calcd. for C10 H9 BrN2 O2: C, 44.61; H, 3.35; Br, 29.74; N, 10.41; Found: C, 44.56; H, 3.40; Br, 29.63; N, 10.36.

Reference： [1]Patent: US5430148,1995,A

7
[ 387-44-0 ]
[ 271-58-9 ]
C₂₃H₁₃F₂N₃O [ No CAS ]

Reference： [1]AMB Express,2015,vol. 5,p. 8

8
[ 74316-55-5 ]
[ 271-58-9 ]
2-((5-bromoquinolin-8-yl)methylamino)benzaldehyde [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2016,vol. 55,p. 8696 - 8700
Angew. Chem.,2016,vol. 128,p. 8838 - 8842,5
[2]Chemistry - A European Journal,2016,vol. 22,p. 11165 - 11169

9
[ 78941-93-2 ]
[ 271-58-9 ]
2-((7-chloroquinolin-8-yl)methylamino)benzaldehyde [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2016,vol. 55,p. 8696 - 8700
Angew. Chem.,2016,vol. 128,p. 8838 - 8842
[2]Chemistry - A European Journal,2016,vol. 22,p. 11165 - 11169

10
[ 644-98-4 ]
[ 271-58-9 ]
C₁₅H₁₆N₂O [ No CAS ]

Reference： [1]Angewandte Chemie - International Edition,2016,vol. 55,p. 8696 - 8700
Angew. Chem.,2016,vol. 128,p. 8838 - 8842,5

11
[ 271-58-9 ]
[ 43039-98-1 ]
quinolin-3-yl(thiazol-2-yl)methanone [ No CAS ]

Reference： [1]Chemical Communications,2017,vol. 53,p. 5302 - 5305

12
[ 1123-86-0 ]
[ 271-58-9 ]
[ 81128-27-0 ]

Reference： [1]Chemical Communications,2017,vol. 53,p. 5302 - 5305

13
[ 271-58-9 ]
[ 135306-45-5 ]
(3,5-difluorophenyl)(quinolin-3-yl)methanone [ No CAS ]

Reference： [1]Chemical Communications,2017,vol. 53,p. 5302 - 5305

14
[ 711-33-1 ]
[ 271-58-9 ]
quinolin-3-yl(4-(trifluoromethyl)phenyl)methanone [ No CAS ]

Reference： [1]Chemical Communications,2017,vol. 53,p. 5302 - 5305

15
[ 17408-16-1 ]
[ 271-58-9 ]
[ 1187167-64-1 ]

Reference： [1]Chemical Communications,2017,vol. 53,p. 5302 - 5305

16
[ 271-58-9 ]
[ 67-68-5 ]
[ 123577-99-1 ]
(3,5-difluorophenyl)(quinolin-3-yl)methanone [ No CAS ]

Reference： [1]Organic Letters,2017,vol. 19,p. 4948 - 4951
[2]RSC Advances,2019,vol. 9,p. 10340 - 10344

17
[ 784-04-3 ]
[ 271-58-9 ]
[ 67-68-5 ]
anthracen-9-yl(quinolin-3-yl)methanone [ No CAS ]

Reference： [1]Organic Letters,2017,vol. 19,p. 4948 - 4951

18
[ 2206-27-1 ]
[ 271-58-9 ]
[ 98-86-2 ]
C₁₆H₉⁽²⁾H₂NO [ No CAS ]

Reference： [1]Organic Letters,2017,vol. 19,p. 4948 - 4951

19
[ 271-58-9 ]
C₁₉H₁₈O₄ [ No CAS ]
C₂₆H₂₃NO₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	With scandium tris(trifluoromethanesulfonate); In dichloromethane; at 20℃; for 2.0h;Molecular sieve;	In a 10 ml round bottom flask add 100 mg of fully dried molecular sieves and 1.0 mlDichloromethane was then added sequentially to cyclopropane 1c (62 mg, 0.2 mmol) andBenzoxazole 2a (27 mg, 0.22 mmol) and triflate(10 mg, 10% mmol). After the reaction mixture was stirred at room temperature for 2 hours, diatomaceous earth was filtered to remove the molecular sieves, and the solvent was added to the residue by distillation to separate the solvent, which was then separated by silica gel column chromatography (eluent: petroleum ether/ethyl acetate (v/v=5/1) ) to get 68mg of product 3ca,Yield 80%.

Reference： [1]Patent: CN107674085,2018,A .Location in patent: Paragraph 0046; 0047; 0048

20
[ 3709-20-4 ]
[ 271-58-9 ]
C₂₀H₁₉NO₅ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	With scandium tris(trifluoromethanesulfonate); In dichloromethane; at 20℃; for 3.0h;Molecular sieve;	In a 50 ml round bottom flask was added 2.0 g of fully dried molecular sieves and20 ml dichloromethane, then cyclopropane 1a (1.0 g, 4.27 mmol) and thenBenzoxazole 2a (0.62 g, 5.13 mmol) and yttrium triflate (210 mg, 10 mmol%). After the reaction mixture was stirred at room temperature for 3 hours, the diatomaceous earth was filtered to remove the molecular sieves, the solvent was removed by distillation, and the solvent was separated by silica gel column chromatography.(The eluent was petroleum ether/ethyl acetate (v/v = 8/1)) to give 1.29 g of product 3aa,Yield 86%.

Reference： [1]Patent: CN107674085,2018,A .Location in patent: Paragraph 0030; 0031; 0032

21
[ 498-66-8 ]
[ 5518-52-5 ]
[ 90-14-2 ]
[ 271-58-9 ]
C₃₆H₃₀NO₄PPd [ No CAS ]

Reference： [1]Applied Organometallic Chemistry,2019,vol. 33

22
[ 498-66-8 ]
[ 5518-52-5 ]
[ 615-37-2 ]
[ 271-58-9 ]
C₃₃H₃₀NO₄PPd [ No CAS ]

Reference： [1]Applied Organometallic Chemistry,2019,vol. 33

23
[ 2932-65-2 ]
[ 271-58-9 ]
[ 67-68-5 ]
C₁₉H₁₇NO [ No CAS ]

Reference： [1]RSC Advances,2019,vol. 9,p. 10340 - 10344

24
[ 271-58-9 ]
[ 1007-15-4 ]
[ 67-68-5 ]
C₁₆H₉BrFNO [ No CAS ]