Skip to main content
. 2023 Oct 27;13(45):31470–31479. doi: 10.1039/d3ra05199d

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
a

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).

b

Isolated yields.

c

8 mol% NGPU (2 : 1 : 5).

d

Isolated yields after recrystallization.