Helvetica Chimica Acta – Vol. 93 (2010)
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114.3; 119.8; 127.9; 128.1; 128.5; 128.7; 129.1; 129.4; 133.6; 134.6; 152.4; 154.4; 156.2; 159.9; 192.8. HR-
ESI-MS: 397.1149 ([M þ Na]þ; calc. 397.1164).
2,3,4,13-Tetrahydro-13-propyl-1H-indazolo[1,2-b]phthalazine-1,6,11-trione (4q). Yellow powder
(86%). M.p. 172 – 1748. IR (KBr): 2956, 2930, 2858, 1656, 1466, 1427, 1368, 1319, 1279, 1176, 1132,
1
1083, 1010, 968, 905, 843, 795, 758, 695, 590, 525. H-NMR (300 MHz): 0.89 (t, J ¼ 7.2, 3 H); 1.10 – 1.28
(m, 2 H); 1.96 – 2.56 (m, 6 H); 3.21 (dt, J ¼ 19.3, 5.5, 1 H); 3.44 (dt, J ¼ 19.3, 5.5, 1 H); 5.65 (s, 1 H);
7.80 – 7.90 (m, 2 H); 8.28 – 8.37 (m, 2 H). 13C-NMR (75 MHz): 13.9; 16.8; 22.5; 24.6; 31.7; 37.1; 63.1; 118.9;
127.7; 128.1; 129.1; 1292; 133.5; 134.6; 153.1; 154.8; 156.3; 193.5. HR-ESI-MS: 333.1211 ([M þ Na]þ; calc.
333.1215).
2-Acetyl-3-methyl-1-phenyl-1H-pyrazolo[1,2-b]phthalazine-5,10-dione (5a). Brown semisolid
(82%). IR (KBr): 2925, 2854, 1689, 1655, 1601, 1490, 1464, 1415, 1353, 13119, 1279, 1204, 1134, 1107,
1075, 1028, 960, 929, 832, 755, 698, 637, 589, 539. 1H-NMR (300 MHz,): 2.06 (s, 3 H); 3.09 (s, 3 H); 6.47 (s,
1 H); 7.29 – 8.35 (m, 9 H). 13C-NMR (75 MHz): 14.4; 30.5; 66.1; 118.9; 127.2; 127.9; 128.2; 128.5; 128.7;
128.8; 129.1; 133.4; 134.1; 136.3; 146.1; 154.1; 156.2; 192.8. HR-ESI-MS: 355.1050 ([M þ Na]þ; calc.
355.1058).
2-Acetyl-3-methyl-1-propyl-1H-pyrazolo[1,2-b]phthalazine-5,10-dione (5c). Brown semisolid
(84%). IR (KBr): 2963, 2931, 2873, 1851, 1774, 1687, 1652, 1465, 1421, 1340, 1292, 1204, 1199, 1125,
1087, 1023, 968, 898, 791, 756, 699, 663, 631, 525. 1H-NMR (300 MHz): 0.88 (t, J ¼ 7.6, 3 H); 1.09 – 1.31 (m,
2 H); 1.71 – 1.88 (m, 1 H); 2.15 – 2.36 (m, 1 H); 2.39 (s, 3 H); 2.90 (s, 3 H); 5.72 (s, 1 H); 7.77 – 7.92 (m,
2 H); 8.26 – 8.37 (m, 2 H). 13C-NMR (75 MHz): 13.6; 14.6; 16.3; 30.3; 32.6; 63.1; 119.6; 127.1; 127.9; 128.6;
129.4; 133.3; 134.2; 145.3; 154.3; 156.3; 193.3. HR-ESI-MS: 321.1220 ([M þ Na]þ; calc. 321.1215).
C. S. thanks UGC, New Delhi, for the award of a fellowship.
REFERENCES
[1] E. C. Franklin, Chem. Rev. 1935, 16, 305; F. W. Bergstrom, Chem. Rev. 1944, 35, 77; F. W.
Lichtenthaler, Acc. Chem. Res. 2002, 35, 728; V. P. Litvinov, Russ. Chem. Rev. 2003, 72, 69; Y. Xu, Q.-
X. Guo, Heterocycles 2004, 63, 903.
[2] W. R. Vaughan, Chem. Rev. 1948, 43, 447; R. A. Clement, J. Org. Chem. 1960, 25, 1724; H. W. Heine,
R. Henrie, L. Heitz, S. R. Kovvali, J. Org. Chem. 1974, 39, 3187; H. W. Heine, L. M. Baclawski, S. M.
Bonser, G. D. Wachob, J. Org. Chem. 1976, 41, 3229; T. Sheradsky, R. Moshenberg, J. Org. Chem.
1986, 51, 3123; L. N. Jungheim, S. K. Sigmund, J. Org. Chem. 1987, 52, 4007; J. M. Indelicato, C. E.
Pasini, J. Med. Chem. 1988, 31, 1227; T. Kappe, C. Kos, Synthesis 1989, 629; C. Turk, J. Svete, B.
ˇ
ˇ
ˇ
ˇ
Stanovnik, L. Golic, S. Golic-Grdadolnik, C. A. Golobic, C. L. Selic, Helv. Chim. Acta 2001, 84, 146;
M. P. Clark, S. K. Laughlin, M. J. Laufersweiler, R. G. Bookland, T. A. Brugel, A. Golebiowski, M. P.
Sabat, J. A. Townes, J. C. VanRens, J. F. Djung, M. G. Natchus, B. De, L. C. Hsieh, S. C. Xu, R. L.
Walter, M. J. Mekel, S. A. Heitmeyer, K. K. Brown, K. Juergens, Y. O. Taiwo, M. J. Janusz, J. Med.
Chem. 2004, 47, 2724.
[3] S. Mavel, I. Thery, A. Gueiffier, Arch. Pharm. Med. Chem. 2002, 335, 7.
[4] R. W. Carling, K. W. Moore, L. J. Street, D. Wild, C. Isted, P. D. Leeson, S. Thomas, D. OꢁConnor,
R. M. McKernan, K. Quirk, S. M. Cook, J. R. Atack, K. A. Wafford, S. A. Thompson, G. R. Dawson,
P. Ferris, J. L. Castro, J. Med. Chem. 2004, 47, 1807; L. J. Street, F. Sternfeld, R. A. Jelley, A. J. Reeve,
R. W. Carling, K. W. Moore, R. M. McKernan, B. Sohal, S. Cook, A. Pike, G. R. Dawson, F. A.
Bromidge, K. A. Wafford, G. R. Seabrook, S. A. Thompson, G. Marshall, G. V. Pillai, J. L. Castro,
J. R. Atack, A. M. MacLeod, J. Med. Chem. 2004, 47, 3642.
[5] Y. Imamura, A. Noda, T. Imamura, Y. Ono, T. Okawara, H. Noda, Life Sci. 2003, 74, 29.
[6] J. S. Kim, H.-J. Lee, M.-E. Suh, H.-Y. P. Choo, S. K. Lee, H. J. Park, C. Kim, S. W. Park, C.-O. Lee,
Bioorg. Med. Chem. 2004, 12, 3683.
[7] A. D. Lebsack, J. Gunzner, B. Wang, R. Pracitto, H. Schaffhauser, A. Santini, J. Aiyar, R. Bezverkov,
B. Munoz, W. Liu, S. Venkatraman, Bioorg. Med. Chem. Lett. 2004, 14, 2463.
`
[8] S. Grasso, G. De Sarro, A. De Sarro, N. Micale, M. Zappala, G. Puia, M. Baraldi, C. De Micheli, J.
Med. Chem. 2000, 43, 2851.