686
Kozmík, Košata, Svoboda, Kuchař:
th e residues were eith er rech rom atograph ed or separated by preparative th in layer ch rom a-
tograph y (20 × 20 cm plates, Merck). Distribution an d yields of isolated products are sum -
m arized in Table I.
Methyl 3-methoxy-4-[(5-nitroindol-3-yl)methyl]benzoate (3). M.p. 161–163 °C (ref.5 m .p.
153–155 °C). 1H NMR: 8.59 d, 1 H, J = 2.2 (H-4); 8.41 bs, 1 H (H-1); 8.09 dd, 1 H, J1 = 8.8,
J2 = 2.2 (H-6); 7.56 s, 1 H (H-3´); 7.55 d, 1 H, J = 8.0 (H-5´); 7.37 d, 1 H, J = 8.8 (H-7); 7.16 d,
1 H, J = 8.2 (H-6´); 7.11 d, 1 H, J = 2.2 (H-2); 4.15 s, 2 H (CH2); 3.95 s, 3 H (OCH3); 3.90 s,
3 H (COOCH3). 13C NMR: 166.9 (CO); 156.8 (C-2´); 141.4 (C-5); 139.1 (C-7a); 134.2 (C-1´);
129.5 (C-6´); 129.4 (C-4´); 126.8 (C-3a); 125.3 (C-2); 122.0 (C-5´); 117.6 (C-4); 117.2 (C-3);
116.6 (C-6); 111.0 (C-3´); 110.9 (C-7); 55.6 (OCH3); 52.2 (COOCH3); 25.3 (CH2).
Methyl 3-methoxy-4-[(5-nitroindol-1-yl)methyl]benzoate (4). M.p. 158.5–160 °C. For C18H16N2O5
(340.3) calculated: 63.53% C, 4.74% H, 8.23% N; foun d: 63.45% C, 4.58% H, 8.18% N. IR:
1720 (CO), 1517 an d 1337 (NO2). 1H NMR: 8.61 d, 1 H, J = 2.2 (H-4); 8.09 dd, 1 H, J1 = 9.3,
J2 = 2.2 (H-6); 7.57 s, 1 H (H-3´); 7.52 d, 1 H, J = 7.7 (H-5´); 7.32 d, 1 H, J = 3.3 (H-2); 7.31 d,
1 H, J = 9.3 (H-7); 6.73 d, 1 H, J = 8.2 (H-6´); 6.72 d, 1 H, J = 3.3 (H-3); 5.38 s, 2 H (CH2);
3.95 s, 3 H (OCH3); 3.90 s, 3 H (COOCH3). 13C NMR: 166.3 (CO); 156.4 (C-2´); 141.6 (C-5);
139.0 (C-7a); 131.5 (C-6´); 131.1 (C-1´); 129.5 (C-4´); 127.6 (C-3a); 127.5 (C-2); 122.1 (C-5´);
118.2 (C-4); 117.3 (C-6); 111.1 (C-3´); 109.5 (C-7); 104.3 (C-3); 55.7 (OCH3); 52.3
(COOCH3); 45.7 (CH2).
Methyl 3-methoxy-4-[(5-nitroindol-2-yl)methyl]benzoate (5). M.p. 177.5–179 °C. For C18H16N2O5
(340.3) calculated: 63.53% C, 4.74% H, 8.23% N; foun d: 63.38% C, 4.68% H, 8.12% N. IR:
3457 (NH), 1718 (CO), 1521 an d 1340 (NO2). 1H NMR: 8.65 bs, 1 H (H-1); 8.46 d, 1 H, J =
2.2 (H-4); 8.02 dd, 1 H, J1 = 8.8, J2 = 2.2 (H-6); 7.61 d, 1 H, J = 8.2 (H-5´); 7.60 s, 1 H (H-3´);
7.25 d, 1 H, J = 9.3 (H-7); 7.25 d, 1 H, J = 8.2 (H-6´); 6.47 s, 1 H (H-3); 4.15 s, 2 H (CH2);
4.00 s, 3 H (OCH3); 3.91 s, 3 H (COOCH3). 13C NMR: 166.5 (CO); 156.6 (C-2´); 140.8 (C-2);
140.8 (C-5); 139.0 (C-7a); 131.7 (C-1´); 130.4 (C-4´); 130.2 (C-6´); 127.8 (C-3a); 122.6 (C-5´);
117.0 (C-4); 117.0 (C-6); 111.7 (C-3´); 110.3 (C-7); 102.5 (C-3); 56.1 (OCH3); 52.3
(COOCH3); 29.6 (CH2).
Methyl 3-methoxy-4-[(5-nitroindol-6-yl)methyl]benzoate (6). M.p. 171–172 °C. For C18H16N2O5
(340.3) calculated: 63.53% C, 4.74% H, 8.23% N; foun d: 63.36% C, 4.49% H, 8.10% N. IR:
3473 (NH), 1717 (CO), 1523 an d 1335 (NO2). 1H NMR: 8.58 bs, 1 H (H-1); 8.42 s, 1 H (H-4);
7.55 d, 1 H, J = 7.7 (H-5´); 7.53 s, 1 H (H-3´); 7.30 m , 1 H (H-2); 7.06 s, 1 H (H-7); 7.02 d,
1 H, J = 7.7 (H-6´); 6.67 m , 1 H (H-3); 4.44 s, 2 H (CH2); 3.84 s, 3 H (OCH3); 3.91 s, 3 H
(COOCH3). 13C NMR: 167.1 (CO); 157.3 (C-2´); 143.6 (C-5); 137.9 (C-7a); 134.2 (C-1´); 129.8
(C-6´); 129.7 (C-4´); 129.0 (C-6); 127.0 (C-2); 125.8 (C-3a); 122.1 (C-5´); 119.1 (C-4); 113.3
(C-7); 111.1 (C-3´); 104.3 (C-3); 55.6 (OCH3); 52.1 (COOCH3); 33.7 (CH2).
Methyl 3-methoxy-4-[(5-nitroindol-7-yl)methyl]benzoate (7). M.p. 174.5–175 °C. For C18H16N2O5
(340.3) calculated: 63.53% C, 4.74% H, 8.23% N; foun d: 63.29% C, 4.61% H, 8.15% N. IR:
3466 (NH), 1719 (CO), 1527 an d 1340 (NO2). 1H NMR: 9.23 bs, 1 H (H-1); 8.47 d, 1 H, J =
1.7 (H-4); 8.03 d, 1 H, J = 1.7 (H-6); 7.61 d, 1 H, J = 0.8 (H-3´); 7.57 dd, 1 H, J1 = 7.9, J2 = 1.0
(H-5´); 7.30 dd, 1 H, J1 = 3.0, J1 = 2.7 (H-2); 7.24 d, 1 H, J = 7.9 (H-6´); 6.68 dd, 1 H, J1 = 3.0,
J2 = 2.7 (H-3); 4.25 s, 2 H (CH2); 4.04 s, 3 H (OCH3); 3.89 s, 3 H (COOCH3). 13C NMR: 166.6
(CO); 156.0 (C-2´); 141.9 (C-5); 138.0 (C-7a); 132.3 (C-1´); 130.5 (C-6´); 130.2 (C-4´); 127.0
(C-2); 123.7 (C-7); 123.7 (C-3a); 123.0 (C-5´); 117.4 (C-6); 116.6 (C-4); 112.2 (C-3´); 105.4
(C-3); 56.3 (OCH3); 52.2 (COOCH3); 31.5 (CH2).
Dimethyl 3,3´-dimethoxy-4,4´-[(5-nitroindol-2,3-diyl)dimethyl]dibenzoate (8). M.p. 208–209 °C.
For C28H26N2O8 (518.5) calculated: 64.84% C, 5.05% H, 5.40% N; foun d: 64.58% C, 4.91% H,
Collect. Czech. Chem. Commun. 2006, Vol. 71, No. 5, pp. 679–690