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. 2020 Oct 8;10(61):37086–37097. doi: 10.1039/d0ra04698a

Multicomponent reaction for the synthesis of tri-substituted 4H-pyrans and tetra-substituted pyranopyrazoles.

graphic file with name d0ra04698a-u1.jpg
Entry Aldehyde Product Time (min) Yielda (%) TON TOF Mp (°C) Ref.
Obtained Reported
1 Benzaldehyde 1a 15 97 107.7 430 209–210 208–210 51
2 4-Chlorobenzaldehyde 1b 15 93 103.3 413.2 172 172–174 51
3 4-Bromobenzaldehyde 1c 10 92 102.2 638.8 178–179 178 52
4 4-Hydroxybenzaldehyde 1d 15 90 100 400 177 175–177 53
5 4-Methoxybenzaldehyde 1e 20 95 105.5 319.8 137 135–137 52
6 4-Methylbenzaldehyde 1f 20 85 94.4 286.2 174–176 175–177 51
7 4-Fluorobenzaldehyde 1g 10 94 104.4 652.7 274–276 274–277 51
8 4-Nitrobenzaldehyde 1h 15 88 97.7 391.1 182–183 180–183 54
9 3-Nitrobenzaldehyde 1i 15 83 92.2 368.8 190 189–191 55
10 2-Nitrobenzaldehyde 1j 15 90 100 400 181–182 181–183 56
11 2-Chlorobenzaldehyde 1k 10 95 105.5 659.7 194–195 193–195 55
12 2-Bromobenzaldehyde 1l 15 95 105.5 422.2 186 185–187 55
13 Benzaldehyde 2a 15 98 108.8 435.5 262–263 261–263 57
14 4-Chlorobenzaldehyde 2b 15 95 105.5 422.2 231–233 231 57
15 4-Bromobenzaldehyde 2c 15 90 100 400 172–174 172–174 58
16 4-Hydroxybenzaldehyde 2d 20 90 100 303 254–256 255–257 59
17 4-Methoxybenzaldehyde 2e 20 88 97.7 296.3 211–212 210–212 60
18 4-Methylbenzaldehyde 2f 25 88 97.7 234 213–215 212–215 61
19 4-Fluorobenzaldehyde 2g 15 90 100 400 239–241 240–242 62
20 4-Nitrobenzaldehyde 2h 20 95 105.5 319.8 247–249 246–248 60
21 3-Nitrobenzaldehyde 2i 20 92 102.2 309.7 194 192–194 60
22 2-Nitrobenzaldehyde 2j 20 95 105.5 319.8 216 216–218 57
23 2-Chlorobenzaldehyde 2k 20 85 94.4 286.2 241–243 240–242 60
24 2-Bromobenzaldehyde 2l 20 83 92.2 279.5 232–233 232–235 61
a

Isolated yield.