2104
K. C. Majumdar et al.
PAPER
IR (KBr): 1650, 1658, 2127, 2207 cm–1.
IR (KBr): 1651, 2925 cm–1.
1H NMR (400 MHz, CDCl3): d = 8.18 (d, J = 9.6 Hz, 1 H), 7.67–
7.69 (m, 2 H), 7.43–7.46 (m, 4 H), 7.28 (d, J = 7.6 Hz, 1 H), 7.12–
7.21 (m, 2 H), 6.97 (d, J = 8.0 Hz, 1 H), 6.87 (t, J = 7.6 Hz, 1 H),
6.77 (d, J = 10.0 Hz, 1 H), 3.65 (s, 3 H), 3.53 (s, 3 H).
1H NMR (400 MHz, CDCl3): d = 7.79–7.82 (m, 2 H), 7.54–7.57 (m,
1 H), 7.44–7.49 (m, 2 H), 7.41–7.43 (m, 1 H), 7.36–7.39 (m, 1 H),
7.30–7.35 (m, 2 H), 7.28 (br s, 2 H), 7.08 (s, 1 H), 4.35–4.44 (m, 1
H), 3.35–3.44 (m, 1 H), 2.26 (s, 3 H), 0.92 (t, J = 7.2 Hz, 3 H).
MS: m/z = 433 (M+).
13C NMR (100 MHz, CDCl3): d = 13.0, 20.9, 45.0, 126.0, 126.4,
127.0, 127.7, 128.2, 128.5, 128.7, 130.1, 130.2, 130.7, 131.1, 132.0,
132.0, 132.5, 133.6, 138.8, 139.1, 143.0, 166.5.
Anal. Calcd for C26H19N5O2: C, 72.04; H, 4.42; N, 16.16. Found: C,
72.25; H, 4.45; N, 16.39.
MS: m/z = 380 (M+).
Compounds 4a–f; 8-Methyl-3-phenyldibenzo[c,g][1,2,3]triazo-
lo[1,5-a][1,5]diazocin-9(8H)-one (4a); Typical Procedure
A solution of the amide 3a (100 mg, 0.28 mmol) in DMF (5 mL)
was heated at 120 °C for 5 h. After completion of the reaction (mon-
itored by TLC), the reaction mixture was cooled and H2O (10 mL)
was added. The mixture was then extracted with EtOAc (3 × 30
mL). The combined organic layers were dried (Na2SO4), filtered,
and concentrated. The crude product was purified by column chro-
matography over silica gel (60–120 mesh) using PE–EtOAc (7:3) as
eluent to obtain the pure product 4a as a solid; yield: 95 mg (95%);
mp 226–228 °C.
Anal. Calcd for C24H20N4O: C, 75.77; H, 5.30; N, 14.73. Found: C,
75.90; H, 5.27; N, 14.98.
4e
Yield: 92%; solid; mp 272–274 °C.
IR (KBr): 1660, 1739, 2928 cm–1.
1H NMR (400 MHz, CDCl3): d = 7.52–7.54 (m, 4 H), 7.50–7.52 (m,
2 H), 7.44–7.48 (m, 2 H), 7.32–7.36 (m, 3 H), 7.12 (d, J = 10.0 Hz,
1 H), 6.18 (d, J = 10.0 Hz, 1 H), 3.37 (s, 3 H).
13C NMR (100 MHz, CDCl3): d = 37.6, 117.5, 118.7, 120.6, 124.4,
125.9, 126.3, 127.1, 129.0, 129.0, 129.3, 130.3, 130.9, 131.5, 131.5,
132.8, 139.4, 139.9, 145.1, 153.5, 158.7, 166.7.
IR (KBr): 1652, 2928 cm–1.
1H NMR (400 MHz, CDCl3): d = 7.66–7.68 (m, 2 H), 7.57–7.59 (m,
1 H), 7.43–7.52 (m, 5 H), 7.32–7.38 (m, 3 H), 7.28–7.30 (m, 1 H),
7.20 (dd, J = 1.6, 12 Hz, 1 H), 3.37 (s, 3 H).
13C NMR (100 MHz, CDCl3): d = 37.8, 126.0, 126.2, 126.8, 127.3,
128.3, 128.7, 128.8, 128.8, 130.0, 130.3, 131.0, 131.1, 131.6, 132.0,
133.0, 143.1, 143.9, 166.9.
MS: m/z = 420 (M+).
Anal. Calcd for C25H16N4O3: C, 71.42; H, 3.84; N, 13.33. Found: C,
71.58; H, 3.87; N, 13.49.
4f
HRMS: m/z calcd for C22H16N4O: 353.1397 [M+ + H]; found:
Yield: 94%; solid; mp 196–198 °C.
IR (KBr): 1655, 1658, 2928 cm–1.
353.1406 [M+ + H].
1H NMR (400 MHz, CDCl3): d = 7.57–7.61 (m, 4 H), 7.43–7.52 (m,
4 H), 7.29–7.30 (m, 3 H), 7.15 (d, J = 10.0 Hz, 1 H), 6.47 (d, J = 9.6
Hz, 1 H), 3.68 (s, 3 H), 3.36 (s, 3 H).
13C NMR (100 MHz; CDCl3): d = 14.1, 37.5, 117.8, 118.6, 124.1,
124.5, 125.9, 126.2, 127.9, 128.8, 128.8, 129.1, 129.3, 130.7, 131.3,
131.7, 133.1, 134.9, 137.8, 140.0, 145.0, 161.2, 167.0.
4b
Yield: 97%; solid; mp 198–200 °C.
IR (KBr): 1642, 2922 cm–1.
1H NMR (400 MHz, CDCl3): d = 7.77–7.80 (m, 2 H), 7.55–7.58 (m,
1 H), 7.47–7.52 (m, 3 H), 7.41–7.45 (m, 2 H), 7.36–7.38 (m, 1 H),
7.32–7.34 (m, 2 H), 7.28–7.31 (m, 3 H), 4.39–4.48 (m, 1 H), 3.38–
3.47 (m, 1 H), 0.93 (t, J = 7.2 Hz, 3 H).
MS: m/z = 433 (M+).
Anal. Calcd for C26H19N5O2: C, 72.04; H, 4.42; N, 16.16. Found: C,
72.19; H, 4.38; N, 16.35.
13C NMR (100 MHz, CDCl3): d = 13.1, 45.2, 126.0, 126.4, 127.3,
128.0, 128.3, 128.6, 128.6, 128.7, 129.9, 130.3, 130.9, 131.1, 131.6,
131.9, 133.4, 141.7, 143.2, 166.5.
MS: m/z = 366 (M+).
Acknowledgment
Anal. Calcd for C23H18N4O: C, 75.39; H, 4.95; N, 15.29. Found: C,
75.25; H, 4.91; N, 15.43.
We thank the DST (New Delhi) and the CSIR (New Delhi) for fi-
nancial assistance. Two of us (K.R. and S.G.) are grateful to the
CSIR (New Delhi) for their fellowships. We also thank the DST
(New Delhi) for providing a 400 MHz NMR spectrometer (Bruker)
and a Perkin-Elmer CHN analyzer under the FIST program.
4c
Yield: 95%; solid; mp 248–250 °C.
IR (KBr): 1647, 2923 cm–1.
1H NMR (300 MHz, CDCl3): d = 7.68 (d, J = 6.3 Hz, 2 H), 7.56–
7.59 (m, 1 H), 7.47 (d, J = 5.4 Hz, 3 H), 7.29–7.37 (m, 5 H), 7.00 (s,
1 H), 3.34 (s, 3 H), 2.24 (s, 3 H).
13C NMR (100 MHz, CDCl3): d = 20.9, 37.8, 125.9, 126.0, 126.7,
127.0, 128.2, 128.8, 130.1, 130.2, 130.9, 131.1, 131.7, 132.1,
132.4, 133.2, 138.9, 140.6, 143.6, 167.1.
References
(1) (a) Huisgen, R.; Knorr, R.; Moebius, L.; Szeimies, G. Chem.
Ber. 1965, 98, 4014. (b) Huisgen, R. In 1,3- Dipolar
Cycloaddition Chemistry; Padwa, A., Ed.; Wiley: New
York, 1984, 1–176.
(2) (a) Alvarez, R.; Valaquez, S.; San, F.; Aquaro, S.; De, C.;
Penro, C. F.; Karlsson, A.; Balzarini, J.; Camarasa, M. J.
J. Med. Chem. 1994, 37, 4185. (b) Valquez, S.; Alvarez, R.;
Perez, C.; Cago, F.; De, C.; Balzarini, J.; Camarasa, M. J.
Antivir. Chem. Chemother. 1998, 9, 481.
MS: m/z = 366 (M+).
Anal. Calcd for C23H18N4O: C, 75.39; H, 4.95; N, 15.29. Found: C,
75.52; H, 4.98; N, 15.16.
(3) Buckle, D. R.; Rockell, C. J. M.; Smith, H.; Spicer, B. A.
J. Med. Chem. 1986, 29, 2262.
4d
Yield: 93%; solid; mp 236–238 °C.
Synthesis 2010, No. 12, 2101–2105 © Thieme Stuttgart · New York