Electric Literature of 4928-87-4, A common heterocyclic compound, 4928-87-4, name is 1,2,4-Triazole-3-carboxylic acid, molecular formula is C3H3N3O2, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.
To an ice-cold solution of the above obtained salt (0.25 g,0.63 mmol) in DMF (0.8 mL), iPr2NEt (0.33 mL, 1.89 mmol) wasadded. The reaction mixture was stirred at 0 C for 10 min and thenTCA (0.064 g, 0.57 mmol) and PyBrOP (0.32 g, 0.68 mmol) wereadded sequentially. The mixture was stirred at ambient temperaturefor 1 h and then it was diluted with EtOAc. The organic phasewas washed once with a 5% aq solution of NaHCO3 and thrice withH2O, dried over Na2SO4 and evaporated to dryness. Compound 9was purified with FCC. Yield: 0.16 g (75%); white foam; Rf(CHCl3/MeOH 9:1): 0.12; IR (KBr, cm1): 3117, 3041, 2931, 1648,1540, 1060; MS (ESI, 30 eV): m/z 417.45 [M+K], 401.24 [M+Na],379.28 [M+H]; HRMS (m/z): [M+H]+ calcd for C15H19N6O6,379.1366. Found: 379.1398; 1H NMR (d6-DMSO): d 9.27(t, J = 5.2 Hz, 1H), 8.30 (s, 1H), 8.14 (d, J = 8.8 Hz, 2H), 7.68 (d,J = 9.2 Hz, 1H), 7.57 (d, J = 8.8 Hz, 2H), 5.82 (br s, 1H), 5.00 (1H,unresolved d), 4.84 (br s, 1H), 4.02-3.94 (m, 1H), 3.54 (unresolveddd, 1H), 3.29 (dd, J = 6.0 and 10.4 Hz, 1H), 3.20 (q, J = 6.8 Hz, 2H),2.36-2.20 (m, 2H); 13C NMR (d6-DMSO): d 170.1 (two C), 156.9,156.3, 152.4, 146.8, 127.8 (two C), 123.2 (two C), 69.8, 60.9, 56.4,36.4, 34.3.
The synthetic route of 4928-87-4 has been constantly updated, and we look forward to future research findings.
Reference:
Article; Magoulas, George E.; Kostopoulou, Ourania N.; Garnelis, Thomas; Athanassopoulos, Constantinos M.; Kournoutou, Georgia G.; Leotsinidis, Michael; Dinos, George P.; Papaioannou, Dionissios; Kalpaxis, Dimitrios L.; Bioorganic and Medicinal Chemistry; vol. 23; 13; (2015); p. 3163 – 3174;,
1,2,3-Triazole – Wikipedia,
Triazoles – an overview | ScienceDirect Topics