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. 2024 Feb 27;14(10):7006–7021. doi: 10.1039/d4ra00123k

The synthesis of pyridine derivatives (1a–15a) catalyzed by ETG-acetamidea.

graphic file with name d4ra00123k-u1.jpg
Entry R Ketone Product Time (h) Yielda (%) Mp. (°C) Ref.
1a H graphic file with name d4ra00123k-u2.jpg graphic file with name d4ra00123k-u3.jpg 3 71b 242–244 237–239 (ref. 44)
2a 4-OMe graphic file with name d4ra00123k-u4.jpg graphic file with name d4ra00123k-u5.jpg 3 47b 239–240 234–236 (ref. 45)
3a 4-Cl graphic file with name d4ra00123k-u6.jpg graphic file with name d4ra00123k-u7.jpg 3 33b 266–268 260–261 (ref. 45)
4a 4-F graphic file with name d4ra00123k-u8.jpg graphic file with name d4ra00123k-u9.jpg 3.5 58b 259–260
5a 2-Cl graphic file with name d4ra00123k-u10.jpg graphic file with name d4ra00123k-u11.jpg 3 46b 259–261 254–257 (ref. 46)
6a 2-F graphic file with name d4ra00123k-u12.jpg graphic file with name d4ra00123k-u13.jpg 3 44b 254–256
7a 4-Br graphic file with name d4ra00123k-u14.jpg graphic file with name d4ra00123k-u15.jpg 3 53b 299–301 255–257 (ref. 45)
8a 4-Me graphic file with name d4ra00123k-u16.jpg graphic file with name d4ra00123k-u17.jpg 3 44b 258–260 256–258 (ref. 46)
9a Furfural graphic file with name d4ra00123k-u18.jpg graphic file with name d4ra00123k-u19.jpg 3 48b 216–218
10a H graphic file with name d4ra00123k-u20.jpg graphic file with name d4ra00123k-u21.jpg 2.5 15c 186–187 185–187 (ref. 47)
11a 4-OMe graphic file with name d4ra00123k-u22.jpg graphic file with name d4ra00123k-u23.jpg 2.5 12c 188–190 192–195 (ref. 48)
12a 4-Cl graphic file with name d4ra00123k-u24.jpg graphic file with name d4ra00123k-u25.jpg 3 46c 185–186 203–205 (ref. 49)
13a 4-F graphic file with name d4ra00123k-u26.jpg graphic file with name d4ra00123k-u27.jpg 3 19c 164–166 164–166 (ref. 50)
14a 4-Br graphic file with name d4ra00123k-u28.jpg graphic file with name d4ra00123k-u29.jpg 3 36c 183–185 186–188 (ref. 50)
15a 4-Me graphic file with name d4ra00123k-u30.jpg graphic file with name d4ra00123k-u31.jpg 3 31c 210–212 215–217 (ref. 49)
231–233 (ref. 51)
a

Reaction conditions: arylaldehyde (1 mmol), malononitrile (1 mmol), cyclohexanone/dimedone (1 mmol), ammonium acetate (1.5 mmol), ETG-acetamide (50 mg) at 80 °C.

b

Isolated yield by crystallization in ethanol (10–15 mL).

c

Isolated yield via column chromatography (n-hexane : EtOAc = 5 : 5).