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. 2022 Jan 16;27(2):558. doi: 10.3390/molecules27020558

Table 2.

A comparison of the substituted 2-mercaptoquinazolin-4(3H)-ones yields1 obtained with selected green methods with literature yields.

graphic file with name molecules-27-00558-i001.jpg
Compounds R 1 Ar/R 2 Ystirring (%) 2 YMW (%) 3 YUS 4 (%) YLit. (%) Mp (°C)
6a H Me 42 39 17 46 [48]; 68 [33]; 60 [49] 264–265
6b H Et 40 18 36 72 [33]; 95 [50] 255
6c H Allyl 24 15 21 35 [33] 206–208
6d H Ph 63 22 34 35 [48]; 90 [33]; 92 [50]; 73 (82) [51]; 61 [49]; 75 (60) [52] 304–305
6e H Bn 62 41 64 50 [48]; 83 [53] 248–250
6f H 4-MePh 27 47 38 94 [50]; 79 (78) [51]; 88 [54], 75 (62) [52] 312–313
6g H 4-FPh 48 32 25 88 [3]; 88 [54] 336–337
6h H 4-ClPh 55 49 41 75 [33]; 89 [50]; 94 [51] 331–332
6i H 4-BrPh 66 24 58 84 [55]; 70 [52] 330–331
6j H 3-OMePh 64 21 57 91 [54]; 65 (50) [52] 285
6k H 3-ClPh 41 12 25 86 [54] 300–301
7a 6-I Me 31 20 40 73 [33] 307–308
7b 6-I Et 25 14 18 10 [33] 290–292
7c 6-I Allyl 22 13 21 20 [33] 234–235
7d 6-I Ph 32 16 22 91 [33]; 70 [52] 350–352
7e 6-I Bn 45 10 28 352
7f 6-I 4-MePh 49 29 47 350–351
7g 6-I 4-FPh 43 22 18 349–350
7h 6-I 4-ClPh 39 31 38 75 [29] 337–339
7i 6-I 4-BrPh 49 30 51 355–357
7j 6-I 3-OMePh 53 25 58 314–315
7k 6-I 3-ClPh 50 25 44 313–315
8a 6-Br Me 21 14 23 64 [49] 280–281
8b 6-Br Et 25 13 17 243–244
8c 6-Br Allyl 40 14 40 242–243
8d 6-Br Ph 36 13 19 63 [49]; 75 [52] 351–353
8e 6-Br Bn 58 27 60 244
8f 6-Br 4-MePh 76 31 41 60 [56] 341–342
8g 6-Br 4-FPh 57 19 28 354–355
8h 6-Br 4-ClPh 62 27 48 344–346
8i 6-Br 4-BrPh 65 33 56 349–350
8j 6-Br 3-OMePh 49 28 30 312–313
8k 6-Br 3-ClPh 57 18 33 305–307
9a 7-Cl Me 58 19 18 327–328
9b 7-Cl Et 22 15 21 265
9c 7-Cl Allyl 47 13 26 248–249
9d 7-Cl Ph 67 19 36 71 (90) [51] 313–314
9e 7-Cl Bn 26 17 34 270–272
9f 7-Cl 4-MePh 42 13 24 73 [51] 307–309
9g 7-Cl 4-FPh 34 18 18 314–315
9h 7-Cl 4-ClPh 50 14 27 76 [53] 302–303
9i 7-Cl 4-BrPh 50 16 38 320–322
9j 7-Cl 3-OMePh 40 25 44 256–257
9k 7-Cl 3-ClPh 39 19 54 248–249
10a 6,8-(Cl)2 Me 36 15 41 246–247
10b 6,8-(Cl)2 Et 19 119 15 184
10c 6,8-(Cl)2 Allyl 21 23 30 179
10d 6,8-(Cl)2 Ph 20 18 19 65 [52] 283–285
10e 6,8-(Cl)2 Bn 51 14 27 206–208
10f 6,8-(Cl)2 4-MePh 25 27 40 70 [52] 244
10g 6,8-(Cl)2 4-FPh 33 22 24 268–269
10h 6,8-(Cl)2 4-ClPh 34 30 30 259–260
10i 6,8-(Cl)2 4-BrPh 60 37 48 280–282
10j 6,8-(Cl)2 3-OMePh 33 14 24 219–220
10k 6,8-(Cl)2 3-ClPh 38 24 43 214–216

1 The yields were calculated based on the anthranilic acid for the product after precipitation; 2 ChCl:urea (1:2), 80 °C, 1 h; 3 ChCl:urea (1:2), 1800 W, 80 °C, 1 h; 4 ChCl:urea (1:2), 50 W, 80 °C, 1 h.