DIBENZO[b,g][1,8]NAPHTHYRIDIN-5-ONES
3299
J ¼ 2.50 Hz), 9.39 (d, 1H, C06-H, J ¼ 8.64 Hz), 11.86 (b s, 1H, C2-NH). 13C NMR
(CDCl3) d: 18.7 (COCH3), 114.3 (C3), 119.4 (C04), 119.3 (C4), 120.5 (C20 ), 121.7
(C060 ), 122.0 (C5), 124.0 (C03), 130.5 (C8), 131.2 (C7), 132.3 (C6), 138.9 (C05), 143.9
=
(C1), 147.3 (C4a), 148.2 (C8a), 150.9 (C2), 202.6 (C O). MS: m=z (%) 334=332=330
(Mþ, 11=28=50), 315 (30), 314 (28), 295 (36), 160 (10), 120 (49), 77 (35), 44 (100).
Anal. calcd. for C17H12N2Cl2O: C, 61.82; H, 3.64; N, 8.49. Found: C, 61.74; H,
3.81; N, 8.34%.
Compound 2d. Colorless prisms. Mp 141–143 ꢀC. Yield: 0.864 g, 73%. IR
1
nmax (cmꢁ1): 3422 (NH), 1629 (C O), 1581, 1517, 1136. H NMR (CDCl3) d: 2.69
=
(s, 3H, COCH3), 7.08–8.02 (m, 8H, C3-, C5-, C6-, C7-, C8-, C03-, C40 -, C50 -H), 9.43
(d, 1H, C06-H, J ¼ 8.66 Hz), 11.58 (b s, 1H, C2-NH). 13C NMR (CDCl3) d: 18.6
(COCH3), 114.3 (C3), 119.8 (C40 ), 119.4 (C4), 120.5 (C0 ), 121.7 (C0 ), 122.5 (C5),
124.0 (C03), 130.8 (C6), 132.0 (C8), 132.8 (C7), 138.9 (C052), 143.9 (C106), 146.9 (C4a),
þ
=
149.6 (C8a), 150.9 (C2), 202.6 (C O). MS: m=z (%) 298=296 (M , 18=56), 295
(30), 281 (10), 268 (48), 160 (12), 120 (46), 77 (18), 44 (100). Anal. calcd. for
C17H13N2ClO: C, 68.92; H, 4.39; N, 9.46. Found: C, 69.03; H, 4.48; N, 9.34%.
Compound 3a. Pale yellow prisms. Mp 168–170 ꢀC. Yield: 1.057 g, 71%. IR
1
nmax (cmꢁ1): 3430 (NH), 1634 (C O), 1579, 1525, 1156. H NMR (CDCl3) d: 2.55
=
(s, 3H, C6-CH3), 6.98–7.82 (m, 11H, C3-, C7-, C8-, C03-, C40 -, C05-, C020-, C300-, C400-,
C050-, C060-H), 7.87 (s, 1H, C5-H), 9.19 (d, 1H, C06-H, J ¼ 8.26 Hz), 11.02 (b s, 1H,
13
C2-NH). C NMR (CDCl3) d: 21.5 (C6-CH3), 114.3 (C3), 119.8 (C04), 122.5 (C4),
123.8 (C20 ), 126.9 (C60 ), 128.3 (C5), 129.4 (C200, C060), 129.7 (C300, C00), 130.1 (C040), 130.0
(C30 ), 131.3 (C8), 133.2 (C7), 133.9 (C6), 136.4 (C50 ), 138.6 (C1005), 142.3 (C10 ), 146.0
þ
=
(C4a), 150.3 (C8a), 151.9 (C2), 168.8 (C O). MS: m=z (%) 374=372 (M , 15=55),
371 (25), 357 (12), 344 (40), 295 (45), 105 (37), 77 (79), 44 (100). Anal. calcd. for
C23H17N2ClO: C, 74.19; H, 4.56; N, 7.53. Found: C, 74.11; H, 4.70; N, 7.41%.
Compound 3b. Pale yellow needles. Mp 166–168 ꢀC. Yield: 1.010 g, 74%. IR
1
=
n
max (cmꢁ1): 3431 (NH), 1631 (C O), 1589, 1524, 1148. H NMR (CDCl3) d: 2.73 (s,
3H, C8-CH3), 7.00–7.95 (m, 11H, C3-, C6-, C7-, C03-, C40 -, C05-, C200-, C300-, C400-, C050-, C060-
H), 7.99 (d, 1H, C5-H, J ¼ 8.32 Hz), 9.35 (d, 1H, C06-H, J ¼ 8.37 Hz), 11.01 (b s, 1H,
13
C2-NH). C NMR (CDCl3) d: 19.8 (C8-CH3), 114.3 (C3), 119.8 (C04), 122.5 (C4),
123.8 (C20 ), 126.9 (C60 ), 128.1 (C5), 129.4 (C200, C060), 129.7 (C300, C00), 130.1 (C040), 130.0
(C30 ), 131.5 (C6), 132.8 (C7), 136.1 (C8), 136.4 (C50 ), 138.6 (C1005), 142.3 (C10 ), 146.1
þ
=
(C4a), 150.1 (C8a), 151.8 (C2), 168.8 (C O). MS: m=z (%) 374=372 (M , 19=64),
371 (15), 357 (22), 344 (33), 295 (41), 105 (47), 77 (75), 44 (100). Anal. calcd. for
C23H17N2ClO: C, 74.19; H, 4.56; N, 7.53. Found: C, 74.31; H, 4.63; N, 7.44%.
Compound 3c. Pale yellow solid. Mp 170–172 ꢀC. Yield: 1.098 g, 70%. IR
nmax (cmꢁ1): 3430 (NH), 1631 (C O), 1585, 1519, 1146. 1H NMR (CDCl3) d:
=
7.02–7.92 (m, 11H, C3-, C7-, C8-, C03-, C04-, C50 -, C020-, C300-, C040-, C500-, C600-H), 8.04 (s,
1H, C5-H), 9.31 (d, 1H, C06-H, J ¼ 8.39 Hz), 10.94 (b s, 1H, C2-NH). 13C NMR
(CDCl3) d: 114.3 (C3), 119.8 (C40 ), 122.3 (C4), 123.8 (C02), 126.9 (C60 ), 127.8 (C5),
129.4 (C200, C600), 129.7 (C300, C500), 130.1 (C400), 130.0 (C03), 130.9 (C8), 131.8 (C7), 133.0
(C6), 136.4 (C05), 138.6 (C010), 142.3 (C10 ), 145.8 (C4a), 150.0 (C8a), 151.7 (C2), 168.8
þ
=
(C O). MS: m=z (%) 396=394=392 (M , 20=42=78), 391 (30), 364 (36), 357 (25),