Green catalytic preparation method of pyrano[4,3-b]pyran derivative
A technology for the preparation of pyran derivatives and catalysis, which is applied in the field of ionic liquid catalysis, can solve the problems of difficult biodegradation of ionic liquids, low utilization rate of raw materials, and complicated post-processing, etc., and achieves industrial scale production, high utilization rate, post-processing Handle simple effects
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Embodiment 1
[0021] 1mmol benzaldehyde, 1mmol malononitrile, 1mmol 4-hydroxy-6-methyl-2-pyrone and 0.04mmol bissulfonate ionic liquid were added to 25ml single port with stirring bar and condenser tube filled with 5ml water in the bottle. Heated to 65°C, reacted for 27 minutes, detected by TLC (thin plate chromatography), the raw material point disappeared, cooled to room temperature, a large amount of solids precipitated, crushed the solids, stood still, and filtered with suction, the obtained filter residue was dried and recrystallized with ethanol to obtain pure 2-amino-7-methyl-4-phenyl-5-oxo-4H,5H-pyrano[4,3-b]pyran-3-carbonitrile, the yield was 96%. The filtrate was directly added with benzaldehyde, malononitrile and 4-hydroxy-6-methyl-2-pyrone for repeated use.
[0022] 2-Amino-7-methyl-4-phenyl-5-oxo-4H, 5H-pyrano[4,3-b]pyran-3-carbonitrile: m.p.236~238℃; IR(KBr) : 3403, 3324, 3207, 3089, 2195, 1714cm -1 ; 1 HNMR (300MHz, CDCl 3 ): δ=2.27(s, 3H, CH 3 ), 4.45(s, 1H, CH), 4.58(...
Embodiment 2
[0024] 1mmol p-chlorobenzaldehyde, 1mmol malononitrile, 1mmol4-hydroxyl-6-methyl-2-pyrone and 0.05mmol bissulfonate ionic liquid were added to 8ml of water with stirring bar and condenser 25ml single mouth bottle. Heated to 70°C, reacted for 32min, detected by TLC (thin plate chromatography), the raw material point disappeared, cooled to room temperature, a large amount of solid precipitated, crushed the solid, stood still, filtered with suction, dried the obtained filter residue and recrystallized with ethanol to obtain pure 2-Amino-7-methyl-4-(4-chlorophenyl)-5-oxo-4H,5H-pyrano[4,3-b]pyran-3-carbonitrile, the yield is 90% . The filtrate was directly added with p-chlorobenzaldehyde, malononitrile and 4-hydroxy-6-methyl-2-pyrone for repeated use.
[0025] 2-Amino-7-methyl-4-(4-chlorophenyl)-5-oxo-4H,5H-pyrano[4,3-b]pyran-3-carbonitrile: m.p.231~232℃ ;IR (KBr): 3409, 3325, 3084, 2189, 1701cm -1 ; 1 HNMR (300MHz, CDCl 3 ): δ=2.26(s, 3H, CH 3 ), 4.46(s, 1H, CH), 4.57(s, 2H...
Embodiment 3
[0027] Add 1mmol p-nitrobenzaldehyde, 1mmol malononitrile, 1mmol4-hydroxyl-6-methyl-2-pyrone and 0.03mmol bissulfonate ionic liquid respectively to a stirring bar and condenser tube filled with 8ml water 25ml single mouth bottle. Heated to 60°C, reacted for 17 minutes, detected by TLC (thin plate chromatography), the raw material point disappeared, cooled to room temperature, a large amount of solids precipitated, crushed the solids, stood still, filtered with suction, dried the obtained filter residue and recrystallized with ethanol to obtain pure 2-Amino-7-methyl-4-(4-nitrophenyl)-5-oxo-4H, 5H-pyrano[4,3-b]pyran-3-carbonitrile, the yield was 92 %. The filtrate was directly added with p-nitrobenzaldehyde, malononitrile and 4-hydroxy-6-methyl-2-pyrone for repeated use.
[0028] 2-Amino-7-methyl-4-(4-nitrophenyl)-5-oxo-4H,5H-pyrano[4,3-b]pyran-3-carbonitrile: m.p.216~218 ℃; IR (KBr): 3400, 3303, 3149, 2297, 1703cm -1 ; 1 HNMR (300MHz, CDCl 3 ): δ=2.25(s, 3H, CH 3), 4.60(...
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