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D. K. Sreenivas, R. Nagarajan
LETTER
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(19) See Supporting Information.
(20) Analytical Data
Compound 4a: CCDC deposition number 854724. Formula:
C21H15N1O1. Unit cell parameters: a = 18.8910 (15),
b = 14.7317 (11), c = 5.3252 (3), space group P21212.
Compound 4ab: CCDC deposition number 854725.
Formula: C21H15N1O1. Unit cell parameters: a = 15.9003 (8),
b = 5.4237 (3), c = 17.1149 (8), space group Pna21.
Compound 4d: CCDC deposition number 854726. Formula:
C22H17N1O2. Unit cell parameters: a = 8.3015 (8),
b = 9.1172 (9), c = 10.6868 (10), a = 83.461 (2), b = 79.759
(2), g = 81.777 (2), space group P1.
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Hudkins, R. L. J. Med. Chem. 2005, 48, 3776.
Compound 6b: CCDC deposition number 854727. Formula:
C29H18Cl3N1O2. Unit cell parameters: a = 9.0516 (13),
b = 10.4572 (20), c = 13.2939 (17), a = 100.684 (14),
b = 101.200(12), g = 101.784 (15), space group P1.
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(22) General Procedure
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J. A. M.; Kiggen, N. M. M.; Langeveld, B. M. W. J. Am.
Chem. Soc. 2004, 126, 6035. (b) Ho, C.-L.; Chi, L.-C.;
Hung, W.-Y.; Chen, W.-J.; Lin, Y.-C.; Wu, H.; Mondal, E.;
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2012, 22, 215.
A mixture of compound 3a (0.10 g, 0.02 mmol), anhyd
KOAc (0.04 g, 0.04 mmol), TBAB (0.06 g, 0.02 mmol), and
Pd(OAc)2 (0.003 g, 5 mol%) in DMF (3.0 mL) was taken in
a Schlenk tube and heated at 140 °C for 3 h with continuous
stirring. After completion of the reaction as monitored by
TLC, the reaction mixture was cooled and poured into cold
H2O (10 mL). A solid precipitate was formed, extracted with
CHCl3 (3 × 20 mL), and washed with H2O (3 × 20 mL)
followed by brine (20 mL) and dried over anhyd Na2SO4.
Evaporation of solvent, and the crude material was purified
by column chromatography over silica gel (100–200 mesh),
using 12% EtOAc in hexanes as eluent to give product 4a in
68% yield. Compounds 4b–g and 6b were obtained using
same procedure.
5-Ethylindeno[1,2-b]carbazol-11 (5H)-one (4a)
Yellow solid; mp 181–182 °C; yield 68%. IR (KBr): 2986,
1697, 1570, 1446, 1331, 1111, 931, 742 cm–1. 1H NMR (400
MHz, TMS, CDCl3): d = 8.39 (s, 1 H), 8.05 (d, 1 H, J = 7.6
Hz), 7.66 (d, 1 H, J = 7.2 Hz), 7.59 (d, 1 H, J = 7.2 Hz),
7.50–7.46 (ddd, 2H, J1 = 1.2 Hz, J2 = 7.6 Hz, J3 = 15.2 Hz),
7.42 (s, 1 H), 7.33–7.27 (m, 3 H), 4.41 (q, 2 H, J = 7.2 Hz),
1.51 (t, 3 H, J = 7.2 Hz). 13C NMR (100 MHz, TMS, CDCl3):
d = 193.2, 144.6, 144.1, 142.6, 140.7, 136.3, 134.1, 128.8,
126.4, 126.2, 123.8, 123.1, 120.6, 120.5, 119.9, 118.0,
109.1, 100.7, 37.9, 14.0. LC–MS (positive mode): m/z = 298
[M + H]+. Anal. Calcd (%) for C21H15NO: C, 84.82; H, 5.08;
N, 4.71. Found: C, 84.65; H, 5.12; N, 4.68.
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2002, 12, 2829. (b) Gingrich, D. E.; Reddy, D. R.; Iqbal, M.
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Synlett 2012, 23, 1007–1012
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