* 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.
Reference：
[1] Journal of the Chemical Society, 1913, vol. 103, p. 2181
[2] Journal of the Chemical Society, 1913, vol. 103, p. 1301
[3] Proceedings of the Chemical Society, London, 1913, vol. 28, p. 333[4] Journal of the Chemical Society, 1913, vol. 103, p. 989
2
[ 7789-69-7 ]
[ 126-81-8 ]
[ 71942-14-8 ]
[ 203808-81-5 ]
[ 838841-06-8 ]
Reference：
[1] Journal of the Chemical Society, 1913, vol. 103, p. 2181
[2] Journal of the Chemical Society, 1913, vol. 103, p. 1301
[3] Proceedings of the Chemical Society, London, 1913, vol. 28, p. 333[4] Journal of the Chemical Society, 1913, vol. 103, p. 989
In toluene; for 12.0h;Heating / reflux; dean stark apparatus;
A mixture of v-1 (0.0089 mol) and v-2 (0.0089 mol) in toluene (50 ml) was stirred and refluxed for 12 h in a Dean Starck apparatus, then cooled to room temperature. The precipitate was filtered, washed with diethyl ether and dried, yielding: 2 g of v-3 (100percent).A mixture of v-3 (0.0106 mol) and v-4 (0.0106 mol) in AcOH (2.6 ml) and EtOH (50 ml) was stirred at 750C for 24 hours, then cooled to room temperature and concentrated under reduced pressure. The residue was taken up in CH2Cl2. The organic layer was washed with K2C O3 10percent, dried (over MgSO4), filtered and the solvent was evaporated. The residue (5.7 g) was purified by column chromatography over silica gel (eluent: CH2C12/CH3OH/NH4OH 100/0/0 to 99/1/0.1). Three fractions were collected and the EPO <DP n="118"/>solvent was evaporated, yielding: 0.27 g of v-5 (4.5percent) (melting point > 2600C), 0.4 g of v-6 (6.7percent) and 0.34 g of v~7 (5.7percent) (melting point > 2600C).A mixture of v-6 (0.0006 mol) and NH2-NH2/H2O (0.003 mol) in EtOH (20 ml) was stirred and refluxed for 6 hours, then concentrated under reduced pressure. The residue was crystallized from CH3CN. The precipitate was filtered off and dried, yielding: 0.12 g (50percent). Part of this fraction (0.04 g) was crystallized from CH3CN. The precipitate was filtered off and dried, yielding: 0.03 g of v-8 (melting point: 248°C).
General procedure: A dry 50?mL flask was charged with 2-aminobenzamides 1 (2.1?mmol), 5,5-dimethyl-1,3-cyclohexanedione 2 (1.0?mmol), iodine (0.026?g, 0.01?mmol) and toluene (10.0?mL). The mixture was stirred at reflux until the reactant 1 was consumed. After the completion of the reaction monitored by TLC, toluene was recovered by distillation under reduced pressure, and the residue was purified by silica column chromatography using ethyl acetate and petroleum ether (1:3) as the eluent to give products 3.#10;
With glucose sulfonic acid; In water; at 90℃; for 3h;
General procedure: A mixture of aromatic aldehydes (1, 2.0 mmol), dimedone (2, 2.0 mmol), 2-naphthol or beta-naphthylamine (3 or 4, 2.0 mmol) and 5 molpercent GSA was stirred in water (2 mL) at 90 °C until completely (monitored by TLC). After the completion, water (20?25 mL) was added to quench the reaction and then the reaction mixture was filtered, concentrated, the precipitate was collected, and purified by 95percent EtOH/DMF (8:1).
With glucose sulfonic acid; In water; at 90℃; for 7h;
General procedure: A mixture of aromatic aldehydes (1, 2.0 mmol), dimedone (2, 2.0 mmol), 2-naphthol or beta-naphthylamine (3 or 4, 2.0 mmol) and 5 molpercent GSA was stirred in water (2 mL) at 90 °C until completely (monitored by TLC). After the completion, water (20?25 mL) was added to quench the reaction and then the reaction mixture was filtered, concentrated, the precipitate was collected, and purified by 95percent EtOH/DMF (8:1).
With perchloric acid * acetic acid; In ethanol; water; at 80℃; for 3h;pH 4.4;Green chemistry;
General procedure: A mixture of 5-amimotetrazole (1 mmol, 0.085 g), appropriateisatin (1 mmol), dimedone (1 mmol, 0.14 g) and [MeC(OH)2]+ClO4?(10 molpercent) was stirred in EtOH/H2O (1:1, 4 mL) at 80 °C. After theindicated time, the reaction was quenched into water (50 mL) andcooled. The precipitated product was separated by centrifugation andpurified by silica gel chromatography to afford the desired product. Allthe products were characterised by melting point, 1H NMR, 13C NMRand LC-MS.
2-amino-4-[4-(di-p-tolyl-amino)-phenyl]-7,7-dimethyl-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
With dmap; In ethanol; for 5h;Reflux;
General procedure: Compounds 1?3 were synthesized according to a reported procedure [11]. A mixture of 1,1-dimethyl-3,5-cyclohexanedione (3,5-cyclohexanedione, 4-hydroxycoumarin) (10 mmol), 4-(di-p-tolyl-amino)-benzaldehyde (10 mmol), malononitrile (10 mmol) and 4-(dimethylamino)pyridine (DMAP) (1 mmol) in ethanol (100 mL) was refluxed for 5 h and then cooled to room temperature. The precipitates were filtered and sequentially washed with ice-cooled water and ethanol and then dried under a vacuum.
3-chloro-7,7,9-trimethyl-6H-pyrido[2,1-b]quinazolin-11(7H)-one[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
82%
With toluene-4-sulfonic acid; In m-xylene; at 150℃; for 8h;Sealed tube;
General procedure: In a sealed tube equipped with a magnetic bar was charged with 2-amino benzamide derivatives (1, 3.67 mmol), cyclic 1,3-diones (2, 3.67 mmol) and TsOH.H2O (1.83mmol) in m-Xylene (5 mL). The reaction mixture was stirred at 150 °C for 8 h. After completion of the reaction, the reaction mass was cooled to room temperature, diluted with EtOAc, gave a water wash and the organic layer was dried over anhydrous Na2SO4 and concentrated in vacuo. The crude product was purified by flash column chromatography (eluent: ethyl acetate/ n-hexane = 10?90) on silica gel to afford the desired product (4a-k).
General procedure: A mixture of o-phenylenediamine (1mmol), dimedone or1,3-cyclohexanedione (1mmol) and Fe(III)-NicTC(at)nSiO2(3.0molpercent, 30mg) was stirred at room temperature for 20min. Then, aldehyde (1mmol) and water (5mL) wereadded to the reaction mixture and stirred for the stipulated period time. Up to the end of the reaction, the catalyst was separated by centrifuge and the filtrate was concentrated under reduced pressure. After that, the oily mixture was dissolved in ethanol and the pure product was obtained by recrystallization from ethanol (Table2). The synthesis of mono and bis-benzodiazepine derivatives was also performed under the same conditions (Scheme2).
9-propyl-3,3,6,6-tetramethyl-3,4,6,7,9,10-hexahydroacridine-1,8-dione[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
50%
With ammonium acetate; In ethanol; for 14h;Reflux;
General procedure: A typical reaction was carried out in a 10mL flask. Dimedone (2mmol), aldehyde (1mmol), ammonium acetate (3mmol), Fe3+/4A (0.1g) and ethanol (3mL) were stirred at reflux temperature for 14h. The progression of the reaction was monitored by TLC. After completion, the solid was filtered, and washed with ethanol, then the filtrate was evaporated. The residue was extracted with dichloromethane and 0.25M NaOH solution. The organic phase was dried over anhydrous sodium sulphate, filtered and the solvent was evaporated. The product was subjected to 1H and 13C NMR spectroscopy.
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