4
ꢀꢀꢀꢀꢁꢀR. Javahershenas and J. Khalafy: A new synthesis of pyrrolo[3,2-d]pyrimidine derivatives
NMR: δ 11.82 (s, 1H, exchanged with D O, OH), 11.52 (s, 1H, exchanged 3057, 2944, 2241, 1690, 1678, 1642, 1561, 1484, 1277, 1098, 1021, 975,
2
−
1 1
with D O, NH), 10.96 (s, 1H, exchanged with D O, NH), 10.47 (s, 1H, 844, 742, 628 cm ; H NMR: δ 12.03 (bs, 1H, exchanged with D O, OH),
2
2
2
exchanged with D O, NH), 7.84 (d, Jꢀ=ꢀ7.2 Hz, 1H, Ar), 7.64 (t, Jꢀ=ꢀ7.8 Hz, 11.73 (s, 1H, exchanged with D O, NH), 8.08 (t, Jꢀ=ꢀ8.1 Hz, 2H, Ar), 7.91
2
2
1
H, Ar), 7.41 (t, Jꢀ=ꢀ7.2 Hz, 2H, Ar), 7.33 (d, Jꢀ=ꢀ7.5 Hz, 2H, Ar), 7.15 (t, (t, Jꢀ=ꢀ7.8 Hz, 1H, Ar), 7.80–7.50 (m, 4H, Ar), 7.41 (d, Jꢀ=ꢀ8.1 Hz, 1H, Ar),
13
13
Jꢀ=ꢀ8.7 Hz, 2H, Ar); C NMR: δ 163.1, 162.0, 161.9, 159.9, 153.0, 151.6, 7.36 (t, Jꢀ=ꢀ7.8 Hz, 1H, Ar), 3.49 (s, 3H, 3-Me), 3.22 (s, 3H, 1-Me); C NMR:
40.4, 132.6, 128.7, 128.2, 124.4, 116.6, 116.5, 115.9, 115.6, 105.8, 100.2, δ 162.1, 158.2, 158.0, 153.4, 153.3, 151.6, 151.0, 145.4, 144.9, 141.2, 138.6,
1
9
6
9.3. Anal. Calcd for C H FN O : C, 62.23 H, 2.98 N, 10.37. Found: C, 132.6, 127.2, 126.7, 126.4, 124.1, 123.8, 116.6, 110.9, 31.1, 27.8. Anal. Calcd
21 12 3 5
2.31 H, 2.90 N, 10.29.
for C H N O : C, 60.00 H, 3.50 N, 12.17. Found: C, 59.95 H, 3.57 N, 12.26.
23 16 4 7
6
-(3,4-Dimethoxyphenyl)-5-(4-hydroxy-2-oxo-2H-chromen- 6-(4-Fluorophenyl)-7-(4-hydroxy-2-oxo-2H-chromen-3-yl)-1,3-
3
-yl)-1,7-dihydro-2H-pyrrolo[2,3-d]pyrimidine-2,4(3H)-dione dimethyl-1,5-dihydro-2H-pyrrolo[3,2-d]pyrimidine-2,4(3H)-
(
4g)ꢁYield 76%; yellow powder; mp >ꢀ300°C; IR ν 3526, 3416, 3200, dione (4m)ꢁYield 74%; white powder; mp 272–274°C (Lit. [22]: yield
max
3
058, 1700, 1681, 1608, 1512, 1445, 1261, 1213, 1126, 1018, 918, 761, 714, 92%; white solid, mp 268–270°C).
−1
1
6
03 cm ; H NMR: δ 11.66 (s, 1H, exchanged with D O, OH), 11.45(s,
2
1
1
H, exchanged with D O, NH), 10.94 (s, 1H, exchanged wit D O, NH), 6-(3,4-Dimethoxyphenyl)-7-(4-hydroxy-2-oxo-2H-chromen-3-yl)-
2
2
0.44 (s, 1H, exchanged with D O, NH), 7.84 (d, Jꢀ=ꢀ7.8 Hz, 1H, Ar), 7.63 1,3-dimethyl-1,5-dihydro-2H-pyrrolo[3,2-d]pyrimidine-2,4(3H)-
2
(
t, Jꢀ=ꢀ7.5 Hz, 1H, Ar), 7.38 (d, Jꢀ=ꢀ8.4 Hz, 1H, Ar), 7.35 (t, Jꢀ=ꢀ7.2 Hz, 1H, dione (4n)ꢁYield 79%; pale yellow powder; mp >ꢀ300°C; IR: ν
max
Ar), 7.02 (s, 1H, Ar), 6.91 (t, Jꢀ=ꢀ8.4 Hz, 1H, Ar), 6.89 (t, Jꢀ=ꢀ8.7 Hz, 1H, 3376, 3198, 2980, 1702, 1683, 1619, 1503, 1440, 1219, 1122, 1027, 976,
Ar), 3.73 (s, 3H, OMe), 3.69 (s, 3H, OMe); 13C NMR: δ 162.1, 161.9, 159.9, 829, 758, 676 cm ; H NMR: δ 11.73 (s, 1H, exchanged with D O, OH),
−1 1
2
1
1
52.9, 151.6, 148.7, 148.2, 140.1, 129.1, 124.8, 124.3, 119.1, 116.6, 112.3, 10.98 (s, 1H, exchanged with D O, NH), 7.86 (d, Jꢀ=ꢀ7.8 Hz, 1H, Ar), 7.64
10.7, 104.9, 100.2, 99.8, 55.9, 55.6. Anal. Calcd for C H N O : C, 61.75 (t, Jꢀ=ꢀ7.5 Hz, 1H, Ar), 7.41 (d, Jꢀ=ꢀ7.5 Hz, 1H, Ar), 7.35 (t, Jꢀ=ꢀ7.8 Hz, 1H,
2
2
3
17
3
7
H, 3.83 N, 9.39. Found: C, 61.80 H, 3.86 N, 9.31.
Ar), 7.05 (s, 1H, Ar), 7.00 (d, Jꢀ=ꢀ8.4 Hz, 1H, Ar), 6.93 (d, Jꢀ=ꢀ8.4 Hz, 1H,
Ar), 3.71 (s, 3H, MeO), 3.64 (s, 3H, MeO), 3.57 (s, 3H, 3-Me), 3.17 (s, 3H,
1
3
6
-(Phenyl)-7-(4-hydroxy-2-oxo-2H-chromen-3-yl)-1,3-dime- 1-Me); C NMR: δ 162.2, 162.0, 158.4, 153.3, 153.0, 151.1, 148.7, 148.6,
thyl-1,5-dihydro-2H-pyrrolo[3,2-d]pyrimidine-2,4(3H)-dione 139.9, 132.6, 129.9, 125.0, 124.5, 119.7, 116.5, 112.3, 111.1, 105.7, 100.0, 99.7,
4h)ꢁYield 77%; pale yellow powder; mp >ꢀ300°C [22].
55.9, 55.6, 31.2, 27.8. Anal. Calcd for C H N O : C, 63.16 H, 4.45 N, 8.84.
(
2
5
21
3
7
Found: C, 63.08 H, 4.54 N, 8.75.
6
-(4-Methylphenyl)-7-(4-hydroxy-2-oxo-2H-chromen-3-yl)-1,3-
dimethyl-1,5-dihydro-2H-pyrrolo[3,2-d]pyrimidine-2,4(3H)-
dione (4i)ꢁYield 86%; pale yellow powder; mp >ꢀ300°C; IR: ν
Acknowledgments: We are grateful to Urmia University for
max
3
1
427, 3197, 3047, 2949, 1687, 1648, 1552, 1500, 1447, 1387, 1280, 1221, the financial support. We also thank Professor R.H. Prager
−1 1
150, 978, 895, 833, 760, 688 cm ; H NMR: δ 11.76 (s, 1H, exchanged
from Flinders University, Australia, for proofreading and
language editing of the manuscript.
with D O, OH), 11.53 (s, 1H, exchanged with D O, 1H of NH), 7.84 (d,
2
2
Jꢀ=ꢀ8.1 Hz, 1H, Ar), 7.64 (t, Jꢀ=ꢀ8.7 Hz, 1H, Ar), 7.38 (t, Jꢀ=ꢀ8.7 Hz, 2H, Ar),
.34 (d, Jꢀ=ꢀ7.5 Hz, 2H, Ar), 7.15 (d, Jꢀ=ꢀ7.8 Hz, 2H, Ar), 3.53 (s, 3H, 3-Me),
7
3
.16 (s, 3H, 1-Me), 2.27 (s, 3H, Me); 1 C NMR: δ 163.1, 157.1, 157.0, 153.4,
3
1
1
6
53.3, 151.6, 151.0, 145.4, 144.0, 141.2, 137.5, 132.6, 128.2, 126.6, 126.5, References
24.2, 123.8, 115.9, 100.9, 31.2, 26.8, 21.2. Anal. Calcd for C H N O : C,
24
19
3
5
7.13 H, 4.46 N, 9.79. Found: C, 67.05 H, 4.50 N, 9.84.
[
1] Ryota, M.; Keisuke, A.; Seijiro, M. Asymmetric indoline synthesis
via intramolecular Aza-Michael addition mediated by bifunc-
tional organocatalysts. Org. Lett. 2013, 15, 3658–3661.
2] Emmadi, N. R.; Atmakur, K.; Bingi, C.; Godumagadda, N. R.;
Kumar, C. G.; Nanubolu, J. B. Regioselective synthesis of 3-ben-
zyl substituted pyrimidino chromen-2-ones and evaluation of
anti-microbial and anti-biofilm activities. Bioorg. Med. Chem.
Lett. 2014, 24, 485–489.
6
-(4-Chlorophenyl)-7-(4-hydroxy-2-oxo-2H-chromen-3-yl)-1,3-
dimethyl-1,5-dihydro-2H-pyrrolo[3,2-d]pyrimidine-2,4(3H)-
dione (4j)ꢁYield 80%; pale yellow powder; mp >ꢀ300°C; IR: ν
[
max
3
452, 3361, 3188, 2954, 1695, 1649, 1608, 1554, 1449, 1389, 1272, 1237,
−1 1
1
164, 1059, 976, 895, 765, cm ; H NMR: δ 11.84 (s, 1H, exchanged with
D O, OH), 11.64 (s, 1H, exchanged with D O, NH), 7.86 (d, Jꢀ=ꢀ7.2 Hz, 1H,
Ar), 7.64 (t, Jꢀ=ꢀ7.5 Hz, 1H, Ar), 7.55‒7.25 (m, 6H, Ar), 3.50 (s, 3H, 3-Me),
2
2
[
[
[
3] Paengsri, W.; Lee, V. S.; Chong, W. L.; Wahab, H. A.; Baramee,
A. Synthesis, antituberculosis activity and molecular docking
studies for novel naphthoquinone derivatives. Int. J. Biol. Chem.
2012, 6, 69–88.
4] Rosowsky, A.; Mota, C. E.; Queener, S. F. Synthesis and anti-
folate activity of 2,4-diamino-5,6,7,8-tetrahydropyrido[4,3-d]
pyrimidine analogues of trimetrexate and piritrexim. J. Hetero-
cycl. Chem. 1995, 32, 335–340.
1
3
3
.31 (s, 3H, 1-Me); C NMR: δ 161.1, 158.3, 153.0, 151.6, 151.1, 132.7, 132.0,
1
31.5, 130.8, 128.9, 128.6, 128.5, 128.4, 124.3, 124.1, 116.6, 100.1, 96.3,
3
1.0, 28.1. Anal. Calcd for C H ClN O : C, 61.41 H, 3.59 N, 9.34. Found:
23 16 3 5
C, 61.33 H, 3.45 N, 9.42.
6
-(4-Methoxyphenyl)-7-(4-hydroxy-2-oxo-2H-chromen-3-yl)-
1
,3-dimethyl-1,5-dihydro-2H-pyrrolo[3,2-d]pyrimidine-2,4(3H)-
dione (4k)ꢁYield 84%; pale yellow powder; mp >ꢀ300°C (Lit. [22]:
yield 93%, white solid, mp 391–393°C).
5] Deyanov, A. B.; Niyazov, R. K.; Nazmetdinov, F. Y.; Syropyatov,
B. Y.; Kolla, V. E.; Konshin, M. E. Amides, nitriles of 2-arylamino-
5
-carboxy(carbethoxy)-6-methylnicotinic acids and 1-aryl-6-car-
6
-(4-Nitrophenyl)-7-(4-hydroxy-2-oxo-2H-chromen-3-yl)-1,3-
dimethyl-1,5-dihydro-2H-pyrrolo[3,2-d]pyrimidine-2,4(3H)-dione
4l)ꢁYield 75%; orange powder; mp >ꢀ300°C; IR: ν 3427, 3149,
bethoxy-7-methyl-4-oxo-1,4-dihydropyrido[2,3-d]pyrimidines
– synthesis and biological activity. Khim.-Farm. Zh. 1991, 25,
26–28.
(
max
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