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. 2021 May 27;11:11199. doi: 10.1038/s41598-021-89572-y

Table 2.

Scope of the Biginelli condensation for the synthesis of 3,4-dihydropyrimidin-2-(1H)-ones catalyzed by MCM-41-APS-PMDA-NHSO3H (1)a.Inline graphic

Entry Aldehyde 3 Product 5 Time (min) Yield (%)b mp °C (Obs.) mp °C (Lit.)
1 4-ClC6H4 graphic file with name 41598_2021_89572_Figc_HTML.gif 35 95 210–211 210–21172
2 C6H5 graphic file with name 41598_2021_89572_Figd_HTML.gif 55 87 235–236 234–23673
3 4-NO2C6H4 graphic file with name 41598_2021_89572_Fige_HTML.gif 50 80 204 224–22774
4 3-NO2C6H4 graphic file with name 41598_2021_89572_Figf_HTML.gif 60 82 293–295 20475
5 4-CH3OC6H4 graphic file with name 41598_2021_89572_Figg_HTML.gif 55 89 201–203 202–20476
6 2-ClC6H4 graphic file with name 41598_2021_89572_Figh_HTML.gif 60 90 211–213 211–21375
7 4-OHC6H4 graphic file with name 41598_2021_89572_Figi_HTML.gif 55 82 234–236 233–23577
8 2-C4H3S– graphic file with name 41598_2021_89572_Figj_HTML.gif 45 84 212–214 210–21278
9 4-Me2NC6H4 graphic file with name 41598_2021_89572_Figk_HTML.gif 45 92 213–215 213–21579
10 4-FC6H4 graphic file with name 41598_2021_89572_Figl_HTML.gif 60 85 180 18080
11 4-OH-3-MeO-C6H3 graphic file with name 41598_2021_89572_Figm_HTML.gif 40 84 188–190 188.581

aReaction conditions: ethyl acetoacetate (2, 1 mmol), aldehydes (3a–k, 1 mmol), urea (4, 1.2 mmol), MCM-41-APS-PMDA-NHSO3H (1, 15 mg) under solvent-free conditions at 80 °C.

bIsolated yields were reported.