M. Bayat, M. Rezaee, and L.-G. Zhu
Vol 000
3
3
8-(2-Hydroxy-phenyl)-9-nitro-3,4,7,8-tetrahydro-1H-pyrido
3J = 7.2 Hz, J = 1.5 Hz, 1H), 6.64 (t, J = 7.5 Hz, 1H),
3
3
[1,2-a] pyrimidin-6(2H)-one (3d). White powder; mp 256-
6.72 (d, J = 7.5 Hz, 1H), 6.81 (d, J = 7.5 Hz, 1H), 7.03
258°C. IR (KBr) νmax /cmÀ1: 3400, 3075, 2924, 1711,
3
(t, J = 7.5 Hz, 1H), 9.68 (s, 1H, OH), 11.62 (br s, 1H,
1609, 1496, 1389, 1222, 1134. 1H-NMR (300 MHz,
NH). 13C-NMR (75.4 MHz, DMSO-d6): δ 23.7, 23.9,
27.3, 32.1, 36.8, 49.8, 50.5, 107.9, 115.9, 119.3, 126.4,
127.1, 128.4, 152.5, 155.4, 169.5. MS (m/z): 317 (M+,
12), 271 (93), 253 (100), 213 (6), 178 (11), 113 (2), 91
(13), 41 (12). Anal. calc. For C16H19N3O4 (317.34): C
2
DMSO-d6): δ 1.98–2.08 (m, 2H), 2.60 (dd, J = 16.2 Hz,
2
3
3J = 1.5 Hz, 1H), 3.09 (dd, J = 16.2 Hz, J = 7 Hz, 1H),
3
3
3.80–3.88 (m, 4H), 4.76 (dd, J = 7 Hz, J = 1.5 Hz,
1H), 6.64 (t, J = 7.5 Hz, 1H), 6.72 (d, J = 7.5 Hz, 1H),
3
2
3
3
6.79 (d, J = 7.5 Hz, 1H), 7.02 (t, J = 7.5 Hz, 1H), 9.69
(s, 1H, OH), 11.65 (br s, 1H, NH). 13C-NMR (75.4 MHz,
DMSO-d6): δ 19.7, 32.0, 36.9, 39.9, 40.7, 108.1, 115.8,
119.4, 126.5, 127.2, 128.4, 153.5, 155.4, 169.1. MS (m/
z): 289 (M+, 5), 243 (52), 225 (87), 185 (13), 146 (26),
118 (84), 89 (73), 56 (100). Anal. calc. For C14H15N3O4
(289.29): C 58.13, H 5.23, N 14.53; found: C 58.3, H
60.56, H 6.03, N 13.24; found: C 60.7, H 6.3, N 13.1.
9-(2-Hydroxy-phenyl)-10-nitro-2,3,4,5,8,9-hexahydropy-
rido[1,2-a] [1,3] diazepin-7(1H)-one (3g).
White powder;
mp 265-267°C. IR (KBr) νmax /cmÀ1: 3450, 3055, 2990,
1724, 1599, 1451, 1378, 1268, 1118. 1H-NMR
(300 MHz, DMSO-d6): δ 1.58–1.95 (m, 4H), 2.66 (dd,
2J = 15.9 Hz, J = 1.5 Hz, 1H), 3.14 (dd, J = 15.9 Hz,
3J = 6.9 Hz, 1H), 3.41–3.84 (m, 2H), 4.21–4.25 (m, 2H),
4.78 (dd, 3J = 6.9 Hz, 3J = 1.5 Hz, 1H), 6.64 (t,
3
2
5.6, N 14.3.
8-(2-Hydroxy-3-methoxyphenyl)-3,3-dimethyl-9-nitro-3,4,
7,8-tetrahydro-1H-pyrido[1,2-a]pyrimidin-6(2H)-one (3e).
3J = 7.8 Hz, 1H), 6.70 (d, J = 7.8 Hz, 1H), 6.81 (d,
3
3J = 7.8 Hz, 1H), 7.03 (t, J = 7.8 Hz, 1H), 9.69 (s, 1H,
3
Light yellow crystals; mp 205-207°C. IR (KBr) νmax
/cmÀ1: 3518, 3306, 2957, 1701, 1628, 1485, 1343, 1222,
OH), 11.23 (br s, 1H, NH). 13C-NMR (75.4 MHz,
DMSO-d6): δ 24.8, 25.2, 32.1, 37.6, 45.2, 45.7, 112.2,
115.8, 119.5, 126.1, 126.5, 128.5, 155.5, 158.9, 170.3.
Anal. calc. For C15H17N3O4 (303.31): C 59.40, H 5.65, N
13.85; found: C 59.1, H 5.9, N 13.6.
1
1136. H-NMR (300 MHz, DMSO-d6): δ 1.03 (s, 2Me),
2
3
2.70 (dd, J = 15.9 Hz, J = 1.5 Hz, 1H), 3.15–3.31 (m,
2
3
4H), 3.58 (dd, J = 15.9 Hz, J = 6.9 Hz, 1H), 3.77 (s,
3
3
6H), 4.78 (dd, J = 6.9 Hz, J = 1.5 Hz, 1H), 6.34 (d,
3J = 7.8 Hz, 1H), 6.62 (t, J = 7.8 Hz, 1H), 6.83 (d,
3
7-(2-Hydroxyphenyl)-2-methyl-8-nitro-2,3,6,7-tetrahydroimi-
3J = 7.8 Hz, 1H), 8.84 (s, 1H, OH), 11.60 (br s, 1H,
NH). 13C-NMR (75.4 MHz, DMSO-d6): δ 23.7, 24.0,
27.3, 31.9, 39.2, 49.9, 50.5, 56.3, 108.1, 111.2, 118.0,
119.1, 127.7, 144.1, 148.2, 152.4, 169.4. MS (m/z): 347
(M+, 23), 301 (100), 269 (19), 201 (5), 161 (11), 118 (5),
77 (10), 41 (19). Anal. calc. For C17H21N3O5 (347.37): C
58.78, H 6.09, N 12.10; found: C 58.6, H 6.3, N 11.8.
Crystal data for 3e C17H21N3O5 (CCDC 1486456):
MW = 346.36, a = 7.2405(5) Å, b = 10.7089(8) Å,
c = 11.7675(16) Å, α = 104.986(10), β = 98.365(9),
γ = 99.840(6), V = 851.01(14) Å3, Z = 2, Dc = 1.352 mg/
m3, F (000) = 366, Mo Kα (λ = 0.71073 Å),
3.09 ≤ 2θ ≤ 25.05, intensity data were collected at 293(2)
K with a Bruker APEX area-detector diffractometer, and
employing ω/2θ scanning technique, and employing ω/2θ
scanning technique, in the range of À7 ≤ h ≤ 8,
À12 ≤ k ≤ 12, À10 ≤ l ≤ 14; the structure was solved by
a direct method, all non-hydrogen atoms were positioned
and anisotropic thermal parameters refined from 3017
observed reflections with R (int) = 0.1308 by a full-
dazo[1,2-a] pyridin-5(1H)-one (3h).
Mixture of two
diastereoisomers. White powder; mp 241-243°C. IR
(KBr) νmax /cmÀ1: 3525, 3281, 2926, 1708, 1635, 1522,
1351, 1230, 1140. Anal. calc. For C14H15N3O4 (289.29):
C 58.13, H 5.32, N 14.53; found: C 58.5, H 5.6, N 14.3.
1
Major isomer (60%): H-NMR (300 MHz, acetone-d6):
3
2
δ 1.50 (d, J = 7.1 Hz, 3H), 2.73 (dd, J = 16.3 Hz,
2
3
3J = 1.5 Hz, 1H), 3.08 (dd, J = 16.3 Hz, J = 8.4 Hz,
1H), 3.48–3.50 (m, 1H), 4.10–4.22 (m, 1H), 4.40–4.50
3
3
(m, 1H), 4.84 (dd, J = 8.4 Hz, 1H), 6.72 (t, J = 6.5 Hz,
3
3
1H), 6.87 (d, J = 7.8 Hz, 1H), 7.01 (d, J = 6.8 Hz, 1H),
3
7.05 (t, J = 7.8 Hz, 1H), 8.70 (s, 1H, OH), 9.31 (br s,
1H, NH). 13C-NMR (75.4 MHz, DMSO-d6): δ 19.6,
33.2, 37.8, 50.9, 51.6, 105.5, 115.8, 119.2, 126.8, 127.7,
128.4, 152.7, 155.3, 167.7.
1
minor isomer (40%): H-NMR (300 MHz, acetone-d6):
3
2
δ 1.40 (d, J = 7.0 Hz, 3H), 2.73 (dd, J = 16.3 Hz,
2
3
3J = 1.5 Hz, 1H); 3.08 (dd, J = 16.3 Hz, J = 8.4 Hz,
1H); 3.60–3.62 (m, 1H), 4.10–4.12 (m, 1H, 2H), 4.60–
3
4.70 (m, 1H, 1H), 4.84 (dd, J = 8.4 Hz, 1H), 6.72 (t,
3
3J = 6.5 Hz, 1H), 6.87 (d, J = 7.8 Hz, 1H), 7.01 (d,
matrix least-squares technique converged to R = 0.0985
and wR2 = 0.3195 [I > 2sigma(I)].
8-(2-Hydroxy-phenyl)-3,3-dimethyl-9-nitro-3,4,7,8-tetrahy-
3
3J = 6.8 Hz, 1H), 7.05 (t, J = 7.8 Hz, 1H), 8.70 (s, 1H,
OH); 9.31 (br s, 1H, NH). 13C-NMR (75.4 MHz,
DMSO-d6): δ 20.9, 33.3, 37.6, 40.8, 52.2, 105.3, 115.8,
dro-1H pyrido [1,2-a]pyrimidin-6(2H)-one (3f).
White
crystals; mp. 228–230°C. IR (KBr) νmax /cmÀ1: 3518,
3435, 2926, 1701, 1623, 1498, 1377, 1222, 1130. 1H-
NMR (300 MHz, DMSO-d6): δ 1.13 (s, 6H), 2.72 (dd,
119.3, 126.9, 128.1, 128.3, 152.9, 155.3, 168.1.
7-(2,5-Dihydroxyphenyl)-8-nitro-2,3,6,7-tetrahydroimidazo
[1,2-a]pyridin-5(1H)-one (3i).
White powder; mp 254-
3
2J = 16.2 Hz, J = 1.5 Hz, 1H), 3.15–3.31 (m, 4H), 3.59
256°C. IR (KBr) νmax /cmÀ1: 3510, 3290, 2920, 1705,
(dd, 2J = 16.2 Hz, 3J = 7.2 Hz, 1H), 4.74 (dd,
1635, 1522, 1350, 1230, 1140. 1H-NMR (300 MHz,
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet