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Table 1 Optimization of various reaction conditions

From: Nanao/organocatalyat SiO2/4-(2-Aminoethyl)-morpholine as a new, reusable, and efficacious catalyst for the synthesis of polyhydroquinolines derivatives and antibacterially active evaluation

Entry

Catalyst

Catalyst (g)

Temp

Solvent

Time (min)

Yield (%)b

1

–

–

70

EtOH

50

40

2

SiCl

0.04

70

EtOH

50

45

3

nano-silica/ 4-(2-Aminoethyl)-morpholine

0.04

70

EtOH

12

95

4

nano-silica/ 4-(2-Aminoethyl)-morpholine

0.04

70

EtOAc

12

70

5

nano-silica/ 4-(2-Aminoethyl)-morpholine

0.04

70

H2O

20

65

6

nano-silica/ 4-(2-Aminoethyl)-morpholine

0.04

70

EtOH/H2O (1:1)

12

95

7

nano-silica/ 4-(2-Aminoethyl)-morpholine

0.04

70

Sovent-free

12

95

8

nano-silica/ 4-(2-Aminoethyl)-morpholine

0.04

r.t

EtOH/H2O (1:1)

50

65

9

nano-silica/ 4-(2-Aminoethyl)-morpholine

0.04

50

EtOH/H2O (1:1)

20

75

11

nano-silica/ 4-(2-Aminoethyl)-morpholine

0.05

70

EtOH/H2O (1:1)

12

95

12

nano-silica/ 4-(2-Aminoethyl)-morpholine

0.02

70

EtOH/H2O (1:1)

20

82

  1. Reaction conditions: malononitrile (1 mmol), 4-nitrobenzaldehyde (1 mmol), dimedone (1 mmol), and nano-SiO2/4-(2-Aminoethyl)-morpholine as the catalyst
  2. bIsolated yield