A preparing method of tetrahydro benzopyran derivatives
A technology of benzopyran derivatives and tetrahydrogen, applied in directions such as organic chemistry, can solve the problems such as difficult to obtain substrate, long reaction route, reaction temperature of toxic solvent, etc., and achieves simple operation, short process route and low cost. Effect
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Embodiment 1
[0015] Weigh 106 mg (1.0 mmol) of benzaldehyde into a 25 mL single-necked bottle, add 5 mL of water, stir and mix, then add 69.3 mg (1.05 mmol) of malononitrile, 147 mg (1.05 mmol) of dimedone ), β-cyclodextrin 22.7 mg (0.02 mmol) was stirred at 25°C, reacted for about 5 hours, TLC detected that there was no raw material, a large amount of white solid was precipitated in the reaction solution, filtered under reduced pressure to obtain a white powdery solid, silica gel column chromatography Purification, petroleum ether / ethyl acetate system elution (petroleum ether:ethyl acetate volume ratio is 10:1), evaporated to dryness under reduced pressure to obtain the product 2-amino-3-cyano-4-phenyl-7,7 -Dimethyl-5-oxo-5,6,7,8-tetrahydro-4 H - Benzopyran 280 mg, yield 95%;
[0016] Product structure characterization:
[0017] Melting point: 230-235°C; IR (KBr) cm -1 : 3403 (NH 2 ), 2962(C-H), 2216(CN), 1677(C=O), 1664(C=C), 1593(C=C); 1 H NMR (500 MHz, DMSO-d 6 ): δ 7.27 (t, J =7...
Embodiment 2
[0019] Weigh 120 mg (1.0 mmol) of p-tolualdehyde into a 25 mL single-necked bottle, add 5 mL of ethanol, stir and mix, then add 69.3 mg (1.05 mmol) of malononitrile and 147 mg of dimedone (1.05 mmol), 11.3 mg (0.01 mmol) of β-cyclodextrin, stirred at 25°C, reacted for 5 hours, no raw materials were detected by TLC, a large amount of white solid was precipitated in the reaction solution, filtered under reduced pressure to obtain a white powdery solid, ethanol ( 95%, mass percent concentration) recrystallized and vacuum dried to obtain the product 2-amino-3-cyano-4-(4-methylphenyl)-7,7-dimethyl-5-oxo-5,6 ,7,8-tetrahydro-4 H - Benzopyran 290 mg, yield 94%;
[0020] Product structure characterization:
[0021]Melting point: 235°C; IR (KBr) cm -1 : 3383 (NH 2 ), 2968(C-H), 2190(CN), 1690(C=O), 1645(C=C), 1606(C=C); 1 H NMR (500 MHz, DMSO-d6): δ 7.07 (d, 2H, ArH), 7.01-7.00 (d, 2H, ArH), 6.94 (s, 2H, NH 2 ), 4.11 (s, 1H), 2.53 (d, 1H, H-8), 2.48 (d, 1H, H-8′), 2.24-2.21 (d, 1H...
Embodiment 3
[0023] Weigh 140 mg (1.0 mmol) of p-chlorobenzaldehyde into a 25 mL single-necked bottle, add 5 mL of ethanol, stir and mix, then add 79.2 mg (1.2 mmol) of malononitrile and 168 mg of dimedone ( 1.2 mmol), α-cyclodextrin 48.7 mg (0.05 mmol) was stirred at 15°C, reacted for 5 hours, no raw materials were detected by TLC, and a large amount of white solid was precipitated in the reaction solution, which was filtered under reduced pressure to obtain a white powdery solid, ethanol (95 %, mass percent concentration) recrystallized and vacuum dried to obtain the product 2-amino-3-cyano-4-(4-chlorophenyl)-7,7-dimethyl-5-oxo-5,6,7 ,8-tetrahydro-4 H - Benzopyran 294 mg, yield 90%;
[0024] Product structure characterization:
[0025] Melting point: 225°C; IR (KBr) cm -1 : 3448 (NH 2 ), 3040(C-H), 2242(CN), 1600(C=O), 1593(C=C), 1487(C=C); 1 H NMR (500 MHz, DMSO-d 6 ):δ 7.34 (d, J = 8.4 Hz, 2H, ArH), 7.16 (d, J = 8.4 Hz, 2H, ArH), 7.04 (s, 2H, NH 2 ), 4.17 (s, 1H), 2.48 (s, 2H, H...
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