Month 2019
Synthesis of 1,2,3-Triazole Moiety to Generate Uracil Molecular Architectures
Through Cu-Catalyzed Azide–Alkyne Cycloaddition
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122.45 (3C5-triazole), 125.43 (5CH─Ar), 128.45
(4CH─Ar), 128.66 (5CH─Ar), 129.25 (5CH─Ar),
130.34 (3C4-triazole), 132.24 (C─Ar), 136.43 (C─Ar),
142.81 (C6), 149.31 (C═N), 158.00 (C═O), 163.40
(C═O). MS (m/z) (%): 744 [M+, 14], 292 (12), 171 (18),
144 (32), 90 (100), 64 (48). Anal. for C41H36N12O3
(744.80): Calcd. C, 66.12; H, 4.87; N, 22.57; found C,
66.32; H, 4.91; N, 22.76.
Synthesis
of
5-amino-6-(prop-2-yn-1-yl)pyrimidine-
2,4(1H,3H)-dione (17). An excess of propargyl bromide
(5 mL, 2) was added to a suspension of compound 1a
(0.498 g, 2 mmol) or compound 18 (0.254 g, 2 mmol)
in acetonitrile as a solvent, and the reaction mixture
was refluxed for 10 h. The formed precipitate was
filtered and recrystallized from DMF/EtOH. Pale yellow
crystals; mp 242–244°C; yield (0.126 g, 76%); 1H
NMR (400 MHz, DMSO-d6): δ = 2.89 (2H, s, CH2),
3.21 (s, 1H, C─CH), 8.17 (s, 2H, NH2), 10.65
(s, 1H, NH), 11.18 (s, 1H, NH). 13C NMR (100 MHz,
DMSO-d6): δ = 34.88 (CH2), 76.50 (≡CH), 79.43
(≡C), 122.29 (C5), 130.68 (C6), 150.75 (C═O), 161.91
(C═O). MS (m/z) (%): 165 [M+, 10], 163 [M+2, 100],
131 (18), 120 (22), 92 (40), 65 (70). Anal. for
C7H7N3O2 (165.15): Calcd. C, 50.91; H, 4.27; N,
25.44; found C, 51.07; H, 4.32; N, 25.62.
Synthesis of 5-amino-6-((1-benzyl-1H-1,2,3-triazol-4-yl)
methyl)pyrimidine-2,4(1H,3H)-dione (19).
(Azidomethyl)
benzene (11) (0.133 g, 1 mmol) was added to the alkyne
substrate 17 (0.165 g, 1 mmol) in THF/H2O (1:1)
(25 mL), and then sodium ascorbate (0.079 g, 0.4 mmol)
and CuSO4.5H2O (0.031 g, 0.2 mmol) were added. After
sonication, the mixture was stirred at room temperature
for the specified time of 12 h. The mixture was
concentrated and poured into 30-mL H2O. A pale yellow
precipitate was formed and filtered to give the product
19. Pale yellow crystals; mp 240–242°C; yield (0.228 g,
76%); 1H NMR (400 MHz, DMSO-d6): δ = 4.16
(s, 2H, CH2), 5.58 (s, 2H, NCH2), 7.21–7.20 (m, 3H,
CH─Ar), 7.36–7.34 (m, 3H, CH─Ar + CHAr-triazole),
8.04 (s, 2H, NH2), 10.39 (s, 1H, NH), 11.06 (s, 1H, NH).
13C NMR (100 MHz, DMSO-d6): δ = 46.21 (CH2),
53.14 (NCH2), 122.63 (C5), 124.82 (C6 + CHAr-triazole),
127.93 (C─Ar), 128.46 (C─Ar), 129.19 (C4-triazole),
136.69 (C─Ar), 150.85 (C═O), 162.42 (C═O). MS (m/z)
(%): 298 (M+, 30), 206 (5), 90 (100). Anal. for
C14H14N6O2 (298.30): Calcd. C, 56.37; H, 4.73; N,
28.17; found C, 56.54; H, 4.77; N, 28.32.
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Journal of Heterocyclic Chemistry
DOI 10.1002/jhet