Synthesis of triazolo[2,1-b]quinazolinone derivatives catalyzed by NGPUa.
| Entry | Ar | R | Product | Time (min) | Yieldb (%) | M.p. (°C) | |
|---|---|---|---|---|---|---|---|
| Found | Reported | ||||||
| 1 | C6H5 | CH3 | 1a | 22 | 96 | 254–257 | 252–254 (ref. 26) |
| 2 | 4-Cl-C6H4 | CH3 | 2a | 20 | 94 | 300–303 | 304–305 (ref. 44) |
| 3 | 2-Cl-C6H4c | CH3 | 3a | 14 | 88 | 286–290 | 288–290 (ref. 45) |
| 4 | 2,4-Cl2-C6H3 | CH3 | 4a | 20 | 90 | >300 | >300 (ref. 46) |
| 5 | 4-Br-C6H4 | CH3 | 5a | 30 | 85d | 292–295 | 287–288 (ref. 44) |
| 6 | 4-NO2-C6H4 | CH3 | 6a | 20 | 91 | 291–293 | 290–294 (ref. 47) |
| 7 | 3-NO2-C6H4 | CH3 | 7a | 22 | 93 | 292–294 | 290–293 (ref. 46) |
| 8 | 4-OCH3-C6H4 | CH3 | 8a | 20 | 95 | 233–235 | 231–233 (ref. 46) |
| 9 | 4-OH-C6H4 | CH3 | 9a | 18 | 97 | >300 | >300 (ref. 31) |
| 10 | 4-OH-3-OCH3-C6H3 | CH3 | 10a | 25 | 85d | 272–277 | 287–290 (ref. 48) |
| 11 | 4-CH3-C6H4 | CH3 | 11a | 20 | 93 | 262–266 | 265–267 (ref. 45) |
| 12 | 2-CH3-C6H4 | CH3 | 12a | 16 | 97 | 305–306 | 299–300 (ref. 28) |
| 13 | C6H5 | H | 13a | 24 | 98 | 298–299 | 296–300 (ref. 32) |
| 14 | 4-Cl-C6H4 | H | 14a | 60 | 80d | 294–295 | 294–296 (ref. 32) |
| 15 | 3,4,5-(OCH3)3–C6H2 | H | 15a | 4 | 98 | >300 | 297–299 (ref. 49) |
| 16 | 4-Br-C6H4 | H | 16a | 27 | 98 | >300 | 306–308 (ref. 32) |
| 17 | 4-CH3-C6H4 | H | 17a | 7 | 97 | >300 | 316–318 (ref. 50) |
| 18 | 3-NO2-C6H4 | H | 18a | 16 | 90 | 298–300 | 292–296 (ref. 32) |
| 19 | 2-CH3-C6H4 | H | 19a | 5 | 98 | >300 | New |
| 20 | 2-Br-C6H4 | H | 20a | 5 | 97 | >300 | New |
| 21 | 4-SCH3-C6H4 | H | 21a | 3 | 95 | >300 | New |
Reaction conditions: aldehyde (1 mmol), 1,3-diketones (dimedone and/or 1,3-cyclohexanediones) (1 mmol) and 3-amino-1,2,4-triazole (1 mmol).
Isolated yields.
8 mol% NGPU (2 : 1 : 5).
Isolated yields after recrystallization.