Development of New Multicomponent Reactions in Eco-Friendly Media-Greener Reaction and Expeditious Synthesis of Novel Bioactive Benzylpyranocoumarins
Table 1
Optimization of the conditions’ reaction using different solvents.
Entry
Catalysts (mmol%)
Solvent
Time (h)
Temperature (°C)
Yielda,b,c (%)
1
No
([BMIM][CF3SO3])
24
210
—
2
No
DMC
24
90
—
3
No
H2O
24
100
—
4
No
EtOH
24
78
—
5
No
CH3CN
24
82
—
6
No
THF
24
66
—
7
No
CH2Cl2
24
40
—
8
No
Toluene
24
110
—
9
No
Glacial AcOH
24
119
—
10
TFA (10)
([BMIM][CF3SO3])
24
210
40
11
HCOOH (10)
([BMIM][CF3SO3])
24
210
45
12
Cu(OAc)2 (10)
([BMIM][CF3SO3])
24
210
—
13
ZnO (10)
([BMIM][CF3SO3])
24
210
Trace
14
Gl. AcOH (5)
([BMIM][CF3SO3])
24
210
65
15
Gl. AcOH (10)
([BMIM][CF3SO3])
24
210
95
16
Gl. AcOH (15)
([BMIM][CF3SO3])
24
210
94
17
Gl. AcOH (20)
([BMIM][CF3SO3])
24
210
85
18
Gl. AcOH (10)
([BMIM][CF3SO3])
30 min
210
95
19
Gl. AcOH (10)
([BMIM][CF3SO3])
40 min
210
85
20
Gl. AcOH (10)
([BMIM][CF3SO3])
1
210
76
21
Gl. AcOH (10)
([BMIM][CF3SO3])
1 : 5 h
210
72
22
Gl. AcOH (10)
([BMIM][CF3SO3])
2
210
75
aAll reactions were carried with hydrazine (0.005 mol), ethyl acetoacetate (0.005 mol), benzaldehyde (0.005 mol), and 4-hydroxycoumarin (0.005 mol). bYield of the isolated product. cThe reaction failed to provide a product. [BMIM][CF3SO3], 1-butyl-3-methylimidazolium trifluoromethanesulfonate.