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. 2019 Apr 25;9(23):12801–12812. doi: 10.1039/c9ra01679a

Comparison of the current method with other reported strategies for synthesizing 2-amino-4-(4-chlorophenyl)-3-cyano-pyrano[3,2-c] chromene-5(4H)-one.

Entry Catalyst Catalyst loading Solvent Temp (°C) Time (min) Yield (%) Ref.
1 SDS 20 mol% H2O 60 150 88 17
2 CuO nanoparticles 15 mol% H2O 100 6 93 31
3 MNP@AVOPc 20 mg 25 15 94 27
4 Urea 10 mol% H2O/EtOH 25 420 93 59
5 POPINO 5 mol% H2O Reflux 10 96 30
6 MNPs@Cu 10 mg 90 8 95 This work
7 DAHP 10 mol% H2O/EtOH 25 240 85 26
8 [Sipim]HSO4 0.08 mmol 100 30 90 28
9 Nano Al2O3 25 mol% EtOH 25 300 89 29
10 TBBDA 0.18 mmol H2O/EtOH Reflux 170 91 32
11 DBU 10 mol% H2O 100 5 94 60
12 t-ZrO2 NPs 10 mol% H2O 80 38 89 61
13 ZnO NPs 10 mol% EtOH Reflux 10 80 62 a
14 Sodium alginate 10 mol% EtOH Reflux 50 93 63 a
15 KF/Al2O3 250 mg DMF 25 60–180 81 64 a
a

Reaction conditions: dimedone (1 mmol), 4-chlorobenzaldehyde (1 mmol), malononitrile (1 mmol).