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. 2022 Jan 27;12:1479. doi: 10.1038/s41598-022-05411-8

Table 2.

Hantzsch synthesis of polyhydroquinoline derivatives in the presence of Zn-MOF in PEG-400 at 80 °C.

graphic file with name 41598_2022_5411_Figb_HTML.gif
Entry Aryl aldehyde Product Time (min) Yield (%)a,b Melting point
Measured Literature
1 graphic file with name 41598_2022_5411_Figc_HTML.gif graphic file with name 41598_2022_5411_Figd_HTML.gif 150 83 216–218 217–21950
2 graphic file with name 41598_2022_5411_Fige_HTML.gif graphic file with name 41598_2022_5411_Figf_HTML.gif 85 96 237–240 234–23750
3 graphic file with name 41598_2022_5411_Figg_HTML.gif graphic file with name 41598_2022_5411_Figh_HTML.gif 120 74 252–255 252–25551
4 graphic file with name 41598_2022_5411_Figi_HTML.gif graphic file with name 41598_2022_5411_Figj_HTML.gif 70 58 247–250 245–24751
5 graphic file with name 41598_2022_5411_Figk_HTML.gif graphic file with name 41598_2022_5411_Figl_HTML.gif 180 69 201–204 203–20450
6 graphic file with name 41598_2022_5411_Figm_HTML.gif graphic file with name 41598_2022_5411_Fign_HTML.gif 150 79 263–265 246–24850
7 graphic file with name 41598_2022_5411_Figo_HTML.gif graphic file with name 41598_2022_5411_Figp_HTML.gif 75 95 173–175 176–17850
8 graphic file with name 41598_2022_5411_Figq_HTML.gif graphic file with name 41598_2022_5411_Figr_HTML.gif 90 85 217–219 216–21850
9 graphic file with name 41598_2022_5411_Figs_HTML.gif graphic file with name 41598_2022_5411_Figt_HTML.gif 90 97 217–219 216–21850
10 graphic file with name 41598_2022_5411_Figu_HTML.gif graphic file with name 41598_2022_5411_Figv_HTML.gif 150 92 227–229 231–23351
11 graphic file with name 41598_2022_5411_Figw_HTML.gif graphic file with name 41598_2022_5411_Figx_HTML.gif 90 91 301–303 303–30550

aIsolated yields.

bReaction conditions: Aromatic aldehyde (1 mmol), dimedone (1 mmol), ethyl acetoacetate (1 mmol), ammonium acetate (1.2 mmol), Zn-MOF (10 mg) and PEG-400 (2 mL) at 80 °C.

cReaction conditions: Aromatic aldehyde (1 mmol), dimedone (2 mmol), ethyl acetoacetate (2 mmol), ammonium acetate (2.4 mmol), Zn-MOF (20 mg) and PEG-400 ( 4 mL) at 80 °C.