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A. ROMDHANE ET AL.
27.8 (d, JP–C = 161.2 Hz), 37.6, 62.7 (d, JP–C = 7.4 Hz), 103.4, 115.1, 117.5, 123.4, 125.2,
127.2, 127.4, 128.3, 128.6, 128.7, 129.9, 130.8, 131.6, 138.1, 142.5, 148.6, 153.2, 154.1,
162.4 (d, JP–C = 9.5 Hz); 31P (121 MHz, CDCl3): δ 21.9; HR-ES-MS [M + H]+ calcd. for
(C27H26N4O4P)+: 501,1674; found: 501.1668.
Compound 4c: 2-methyldimethoxyphosphoryl-14-(4-ethyl)phenyl-4H-naphto
[2,1-b] pyrano[3,2-e][1,2,4] triazolo[1,5-c]pyrimidine: white solid; mp 224 ◦C–225 ◦C;
IR (KBr, cm−1) ν: 1625 (C N), 1225 (P O), 985 (P–O–C); 1H NMR (300 MHz, CDCl3):
δ 1.07 (t, J = 8.8 Hz, 3H), 2.53 (q, J = 8.8 Hz, 2H), 3.70 (d, JP–H = 25.2 Hz, 2H), 3.83 (d,
JP–H = 12.2 Hz, 3H), 3.85 (d, JP–H = 12.5 Hz, 3H), 6.36 (s, 1H), 6.92–8.10 (m, 10Harom.),
9.13 (s, 1H); 13C NMR (75 MHz, CDCl3): δ 15.2, 27.1 (d, JP–C = 161.8 Hz), 28.3, 37.7,
53.2 (d, JP–C = 7.2 Hz), 103.7, 115.1, 117.5, 123.5, 125.2, 127.3, 128.0, 128.2, 128.6,
129.8, 130.9, 131.6, 137.9, 139.8, 143.1, 148.5, 153.3, 154.1, 162.1 (d, JP–C = 9.7 Hz); 31
P
(121 MHz, CDCl3): δ 24.5; HR-ES-MS [M + H]+ calcd. for (C27H26N4O4P)+: 501.1738;
found: 501.1733.
Compound 4d: 2-methyldiethoxyphosphoryl-14-(4-ethyl)phenyl-4H-naphto[2,
◦
◦
1-b] pyrano[3,2-e][1,2,4] triazolo[1,5-c]pyrimidine: white solid; mp 254 C–255 C;
IR (KBr, cm−1) ν: 1635 (C N), 1230 (P O), 980 (P–O–C); 1H NMR (300 MHz, CDCl3):
δ 0.91 (t, J = 8.8 Hz, 3H), 1.16 (t, J = 8.2 Hz, 6H), 2.51 (q, J = 8.8 Hz, 2H), 3.66 (d, JP–H
=
25.4 Hz, 2H), 4.14–4.21 (m, 4H), 6.40 (s, 1H), 7.01–8.02 (m, 10Harom.), 9.05 (s, 1H); 13
C
NMR (75 MHz, CDCl3): δ 15.1, 16.4 (d, JP–C = 6.9 Hz), 27.3 (d, JP–C = 161.3 Hz), 28.3,
37.2, 62.7 (d, JP–C = 7.1 Hz), 103.7, 115.2, 117.5, 123.4, 125.2, 127.4, 128.1, 128.2, 128.6,
129.8, 130.8, 131.6, 137.9, 139.8, 143.1, 148.5, 152.9, 154.2, 162.1 (d, JP–C = 9.5 Hz); 31
P
(121 MHz, CDCl3): δ 21.9; HR-ES-MS [M + H]+ calcd. for (C29H30N4O4P)+: 529.2008;
found: 529.2014.
Compound 4e: 2-methyldimethoxyphosphoryl-14-(4-methoxy)phenyl-4H-naph
to[2,1-b] pyrano[3,2-e] [1,2,4]triazolo[1,5-c]pyrimidine: white solid; mp 262 ◦C–263 ◦C;
IR (KBr, cm−1) ν: 1630 (C N), 1220 (P O), 990 (P–O–C); 1H NMR (300 MHz, CDCl3):
δ 3.63 (d, JP–H = 21.6 Hz, 2H), 3.66 (s, 3H), 3.84 (d, JP–H = 12.4 Hz, 3H), 3.86 (d, JP–H
= 12.7 Hz, 3H), 6.36 (s, 1H), 6.69–7.96 (m, 10Harom.), 9.08 (s, 1H); 13C NMR (75 MHz,
CDCl3): δ 26.8 (d, JP–C = 161.3 Hz), 36.7, 53.2 (d, JP–C = 7.4 Hz), 55.1, 103.7, 113.9,
115.1, 117.5, 123.5, 125.2, 127.4, 128.6, 129.4, 129.8, 130.8, 131.6, 134.8, 137.9, 148.4,
153.0, 154.1, 158.6, 161.8 (d, JP–C = 9.5 Hz); 31P (121 MHz, CDCl3): δ 24.5; HR-ES-MS
[M + H]+ calcd. for (C26H24N4O5P)+: 503.1317; found: 503.1323.
Compound 4f: 2-methyldiethoxyphosphoryl-14-(4-methoxy)phenyl-4H-naphto
[2,1-b] pyrano[3,2-e] [1,2,4]triazolo[1,5-c]pyrimidine: white solid; mp 268 ◦C–269 ◦C;
IR (KBr, cm−1) ν: 1615 (C N), 1230 (P O), 995 (P–O–C); 1H NMR (300 MHz, CDCl3):
δ 1.24 (t, J = 8.8 Hz, 6H), 3.60 (d, JP–H = 22.3 Hz, 2H), 3.66 (s, 3H), 4.02–4.17 (m, 4H),
6.25 (s, 1H), 6.60–7.82 (m, 10Harom.), 8.98 (s, 1H); 13C NMR (75 MHz, CDCl3): δ 16.4 (d,
JP–C = 6.9 Hz), 27.8 (d, JP–C = 161.2 Hz), 36.7, 55.1, 62.7 (d, JP–C = 7.1 Hz), 103.7, 113.9,
115.2, 117.5, 123.4, 125.1, 127.3, 128.6, 129.4, 129.8, 130.8, 131.6, 134.8, 137.9, 148.5,
153.1, 153.9, 158.5, 162.3 (d, JP–C = 9.3 Hz); 31P (121 MHz, CDCl3): δ 22.0; HR-ES-MS
[M + H]+ calcd. for (C28H28N4O5P)+: 531.1601; found: 531.1608.
Compound
4g:
2-methyldiethoxyphosphoryl-14-(4-isopropyl)phenyl-4H-
naphto[2,1-b] pyrano[3,2-e] [1,2,4]triazolo[1,5-c]pyrimidine: white solid; mp 228
◦
1
◦C–229 C; IR (KBr, cm−1) ν: 1625 (C N), 1225 (P O), 985 (P–O–C); H NMR (300
MHz, CDCl3): δ 1.12 (d, J = 6.8 Hz, 6H), 1.39 (t, J = 8.2 Hz, 6H), 2.72–2.82 (m, 1H),
3.56 (d, JP–H = 22.5 Hz, 2H), 4.12–4.24 (m, 4H), 6.36 (s, 1H), 6.92–8.19 (m, 10Harom.),
9.11 (s, 1H); 13C NMR (75 MHz, CDCl3): δ 16.4 (d, JP–C = 6.9 Hz), 23.7, 27.8 (d, JP–C
=