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Messere et al.
d, J ¼ 16.0 Hz, H-2), 7.75 (1H, d, J ¼ 16.0 Hz, H-3), 6.63 (1H, d, J ¼ 9.2 Hz,
H-30), 7.94 (1H, dd, J ¼ 3.0 e 9.2 Hz, H-40), 8.30 (1H, d, J ¼ 3.0 Hz, H-60).
Compound 9. 1H-NMR (500 MHz, CD3OD) d: 7.90 (1H, dd, J ¼ 2.0 e
7.6 Hz, H-3), 6.33 (1H, t, J ¼ 7.6 Hz, H-4), 7.49 (1H, dd, J ¼ 2.0 e 7.6 Hz,
H-5), 8.08 (1H, d, J ¼ 13.0 Hz, H-10), 8.61 (1H, d, J ¼ 13.0 Hz, H-20); 13C-
NMR (125 MHz, CD3OD) d: 126.9 (C-1), 150.9 (C-2), 135.8 (C-3), 111.1
(C-4), 137.0 (C-5), 139.4 (C-6), 140.6 (C-10), 137.0 (C-20). Elemental analysis.
Calcd. for C8H6N2O5: C 45.72, H 2.88, N 13.33; found C 45.70, H 2.91, N
13.23. EI-MS: m/z 210 [M]þ. IR cm21: 1621, 1537, 1329. Compound 10.
1H-NMR (500 MHz, CD3OD) d: 6.48 (1H, d, J ¼ 9.6 Hz, H-6), 7.95 (1H,
dd, J ¼ 3.2 e 9.6 Hz, H-5), 8.26 (1H, d, J ¼ 3.2 Hz, H-3), 8.06 (1H, d,
12.8 Hz, H-10), 8.50 (1H, d, J ¼ 12.8 Hz, H-20); 13C-NMR (125 MHz,
CD3OD) d: 122.9 (C-1), 163.9 (C-2), 119.8 (C-3), 129.1 (C-4), 137.0 (C-5),
122.9 (C-6), 139.3 (C-10), 132.0 (C-20). Elemental analysis. Calcd. 10 for
C8H6N2O5: C 45.72, H 2.88, N 13.33; found C 45.65, H 2.68, N 13.21. EI-
1
MS: m/z 210 [M]þ. IR cm21: 1623, 1540, 1328. Compound 12. H-NMR
(500 MHz, CD3OD) d: 6.62 (1H, d, J ¼ 16.0 Hz, H-2), 7.56 (1H, d,
J ¼ 16.0 Hz, H-3), 7.34 (1H, d, J ¼ 1.6 Hz, H-20), 8.09 (1H, d, J ¼ 8.6 Hz,
H-50), 7.26 (1H, dd, J ¼ 1.6 e 8.6 Hz, H-60). Compound 13. 1H-NMR
(500 MHz, CD3OD) d: 6.32 (1H, d, J ¼ 15.6 Hz, H-2), 7.91 (1H, d,
J ¼ 15.6 Hz, H-3), 6.91 (1H, d, J ¼ 2.6 Hz, H-20), 6.77 (1H, dd, J ¼ 2.6 e
9.0 Hz, H-40), 7.98 (1H, d, J ¼ 9.0 Hz, H-50). Elemental analysis. Calcd. 10
for C9H7NO5: C 51.68, H 3.37, N 6.70; found C 51.65, H 3.12, N 6.58. EI-
1
MS: m/z 209 [M]þ. IR cm21: 1682, 1536, 1329. Compound 15. H-NMR
(500 MHz, CD3OD) d: 6.92 (d, 1H, J ¼ 9.4 Hz, H-6), 7.00 (d, 1H,
J ¼ 1.8 Hz, H-3), 7.13 (dd, 1H, J1 ¼ 1.8 HHz, J2 ¼ 9.4 Hz, H-5), 7.52
(d, 1H, J ¼ 16.0 Hz, H-10), 7.94 (d, 1H, J ¼ 16.0 Hz, H-20), 4.01 (3H, s,
CH3). Compound 16. 1H-NMR (500 MHz, CD3OD) d: 7.21 (1H, d,
J ¼ 1.6 Hz, H-3), 7.95 (1H, d, J ¼ 1.6 Hz, H-5), 7.56 (1H, d, J ¼ 13.6 Hz,
H-10), 7.94 (1H, d, J ¼ 13.6 Hz, H-20), 4.01 (3H, s, CH3). Elemental analysis.
Calcd. 10 for C9H8N2O6: C 45.01, H 3.36, N 11.66; found C 44.98, H 3.18, N
11.25. EI-MS: m/z 240 [M]þ. IR cm21: 1549, 1341, 1273, 1042.
ACKNOWLEDGMENTS
`
This work was supported by Ministero dell’Istruzione dell’Universita e
della Riccera (MIUR) (L.488/92) in the frame of the project P2 “Ambiente
terrestre: Chimica per l’Ambiente.” NMR experiments were performed on
500-MHz instruments supplied by INCA (Consorzio Nazionale Interuniversi-
tario “la Chimica per l’Ambiente,” L. 488/92), project P0.