* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
With sodium perchlorate; In acetonitrile; at 20 - 25℃;Electrolysis;
General procedure: A 0.1 M NaClO4solution (50 ml) in MeCN containing NH4SCN (6 mmol, 0.46 g) and indole (1a)(2 mmol, 0.24 g) was placed in a glass cell with coaxally positioned Ptelectrodes (San. = 26 cm2, Scat. = 10 cm2). The electrolysis was performed atE = 0.70 V vs SCE (CPE) or at j = 2.5 mA/cm2 (GE). After passing of 2.1 F ofelectricity in CPE (or 2.5 F in GE) calculated on the basis of 1 F/NH4SCN mol, theelectrolysis was terminated and the MeCN was distilled off. H2O (10 ml) wasadded and the residue was extracted with CH2Cl2 (4 25 ml). The extractswere combined, dried over anhydrous Na2SO4, filtered and the solvent wasdistilled off. The residue was purified by column chromatography on silica gel(eluent-a mix of light petroleum and EtOAc with a buildup of the volumefraction of the latter from 5% to 20%) to afford pure 3-thiocyanato-1H-indole
N-[3-(4-methylphenyl)-1,2-oxazol-5-yl]acetamide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
82%
With pyridine; In acetonitrile; at 0℃; for 3.0h;Inert atmosphere; Reflux;
General procedure: A solution of 5-aminoisoxazole 6 (50 mmol) and pyridine(100 mmol) in acetonitrile (800 mL) was cooled to 0C and treated with acetyl chloride (50 mmol). The resulting mixture was heatedat reflux for 3 h, cooled to r.t., concentrated in vacuo and the residue was treated with water (800 mL). The resulting precipitate wasisolated by filtration and crystallized from ethanol.
With hydroxylamine; sodium hydroxide; In water; for 14.0h;Inert atmosphere; Reflux;
General procedure: Ketonitrile 5 (100 mmol) was added to 15% aqueous NaOH solution(100 mL) followed by hydroxylamine (200 mmol). The resulting mixture was heated at reflux for 14 h, cooled down to r.t., theresulting precipitate was isolated by filtration and crystallized from isopropyl alcohol.
2-(benzisothiazolin-3-one-2-yl)-N-(3-(p-tolyl)isoxazol-5-yl)acetamide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
62.8%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 30℃; for 40.0h;
In a 100ml four-necked flask, <strong>[28883-91-2]3-p-tolyl-5-aminoisoxazole</strong> and benzisothiazolin-3-one-2-yl acetic acid, Its molar ratio is 1:1.5. Dissolve with DMF (N,N-dimethylformamide), Adding HOBT (1-hydroxybenzotriazole) and EDCI [1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride], HOBT, The molar ratio of EDCI to <strong>[28883-91-2]3-p-tolyl-5-aminoisoxazole</strong> is 1.5:1:1. The reaction was completed at 30 C for 40 h. The solution was poured into water and a large amount of solid was precipitated. Filtration, caustic washing, pickling, and washing. The crude product was obtained by column chromatography (ethyl acetate: petroleum ether = 1:1). Yield: 62.8%. Melting point: 221 to 223 C.
5-((N,4-dimethylphenyl)sulfonamido)-4-phenyl-2-(p-tolyl)-1H-pyrrole-3-carboxamide[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
96%
With silver(I) triflimide; In 1,2-dichloro-ethane; at 80℃; for 2.0h;
General procedure: To a stirred solution of ynamide 4a (57.0 mg, 0.2 mmol) in DCE (2.0 mL, 0.1 M) was added isoxazol-5-amine 8a (21.6 mg, 0.22 mmol, 1.1 equiv), followed by AgNTf2 (3.9 mg, 5 mol %). The resulting mixture was placed into an oil bath of 80 C with stirring for 2 h generally, monitoredby TLC. After completion, the reaction mixture was cooled and the desired product was precipitated. The solid was filtered and washed with DCM twice, then dried in a vacuum drying oven at 50 C for 24 h to give the pure pyrrole product 10aa, 75.8 mg, 99% yield. For products 10ab-ae, 10ka-la, the purification method was as follows: evaporation of volatiles under reduced pressure to give the residue, which was suffered from column chromatographyon silica gel (petrol ether/ethyl acetate 1:1-1:2, v/v) to afford the pure pyrrole.
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