Table 1 Optimization of the reaction conditions for the Hantzsch condensation of para-Chlorobenzaldehyde, dimedone, ethyl acetoacetate, and ammonium acetate as the model reaction for the synthesis of polyhydroquinolines.

From: Microporous hierarchically Zn-MOF as an efficient catalyst for the Hantzsch synthesis of polyhydroquinolines

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Entry

Catalyst

Amount Catalyst (mg)

Solvent

Temperature (°C)

Time (min)

Yield (%)a,b

1

–

–

PEG-400

80

85

30

2

4,6-Diamino-2-pyrimidinethiol

10

PEG-400

80

85

41

3

Zn(NO3)2.6H2O

10

PEG-400

80

85

30

4

Zn-MOF

5

PEG-400

80

85

75

5

Zn-MOF

6

PEG-400

80

85

79

6

Zn-MOF

10

PEG-400

80

85

96

7

Zn-MOF

12

PEG-400

80

85

92

8

Zn-MOF

10

EtOH

80

195

83

9

Zn-MOF

10

H2O

80

120

N.R

10

Zn-MOF

10

DMF

80

210

60

11

Zn-MOF

10

DMSO

80

95

70

12

Zn-MOF

10

PEG-400

25

120

N.R

13

Zn-MOF

10

PEG-400

60

85

21

14

Zn-MOF

10

PEG-400

100

85

44

  1. aIsolated yield.
  2. bReaction conditions: 4-Chlorobenzaldehyde (1 mmol), dimedone (1 mmol), ethyl acetoacetate (1 mmol), ammonium acetate (1.2 mmol), catalyst (mg) and solvent (2 mL).