4300
L.-T. An et al. / Tetrahedron Letters 48 (2007) 4297–4300
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Figure 1. X-ray analysis of compound 3j.
9. Review on application of SA, please see: (a) Wang, B.
Synlett 2005, 1342; for recent example, see: (b) Kumar, R.
S.; Nagarajan, R.; Vijay, K.; Perumal, P. T. Lett. Org.
Chem. 2005, 2, 458; (c) Yadav, J. S.; Rao, P. P.; Sreenu,
D.; Rao, R. S.; Kumar, V. N.; Nagaiah, K.; Prasad, A. R.
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(h) Wang, B.; Gu, Y.; Song, G.; Yang, T.; Yang, L.; Suo,
J. J. Mol. Catal. A: Chem. 2005, 233, 121.
O2N
Ar
NO2
10 mol% SA
r.t.
+
Ar
N
N
H
H
Scheme 3.
Acknowledgements
We thank the Key Laboratory of Organic Synthesis of
Jiangsu Province and Suzhou Scientific Committee for
financial supports (JSK016 and SG 0219).
10. General procedure for synthesis of compound 3a: Indole
0.12 g (1 mmol), b-nitrostyrene (1.1 mmol) and SA (Sul-
famic acid) 0.01 g (0.1 mmol) were mixed, followed by
heating at 60 ꢁC. After the completion of the reaction
monitored by TLC (about 30 min), the mixture was
subjected to short column chromatography (acetone–
petroleum ether 1:8 as eluent) to give pure 3a. Brown
Supplementary data
Supplementary data associated with this article can be
1
solid, mp 97–99 ꢁC, H NMR (CDCl3, 300 MHz): d 4.88–
5.20 (m, 3H, CHCH2NO2), 6.97 (s, 1H, C@CH), 7.04–7.44
(m, 9H, ArH), 8.06 (s, 1H, NH). 13C NMR (CDCl3,
75 MHz): d 42.0, 80.0, 111.9, 114.8, 119.4, 120.4, 122.1,
123.1, 126.5, 128.0, 128.2, 129.4, 136.9, 139.6. HRMS:
calcd for C16H14N2O2 266.1055, found 266.1055.
References and notes
11. Toda, F. Organic Solid-State Reactions; Springer, 2002.
12. X-ray data for 3j have been deposited at the Cambridge
Crystallographic Data Centre, deposition number CCDC
630885. Copies of the data can be obtained free of charge
on application to CCDC, 12 Union Road, Cambridge
CB21EZ, UK (fax: +44 1223 336 033; e-mail: deposit@
ccdc.cam.ac.uk). Crystal data for 3j: C17H16N2O3;
Mr = 296.32, colourless block crystals, 0.50 · 0.30 ·
1. (a) Trost, B. M.. Acc. Chem. Res. 2002, 35, 695; (b) Trost,
B. M. Science 1991, 254, 1471.
2. (a) Ono, N. The Nitro Group in Organic Synthesis; Wiley-
VCH: New York, 2001; (b) Seebach, D.; Colvin, E. W.;
Lehr, F.; Weller, T. Chimia 1979, 33, 1; (c) Calderari, G.;
Seebach, D. Helv. Chim. Acta 1995, 68, 1592.
3. See review: Berner, O. M.; Tedeschi, L.; Enders, D. Eur. J.
Org. Chem. 2002, 1877.
4. Olah, G. A.; Krishnamurty, R.; Prakash, G. K. S. Friedel–
Crafts alkylation. In Comprehensive Organic Synthesis, 1st
ed.; Trost, B. M., Fleming, I., Eds.; Pergamon: Oxford,
1991; Vol. III, p 293.
0.10 mm,
monoclinic,
space
group
P21/n,
˚
˚
˚
a = 8.4935(15) A, b = 9.5430(16) A, c = 18.326(3) A, b =
3
3
˚
100.636(4)ꢁ, Z = 4, V = 1459.8(4) A , Dc = 1.348 g/cm ,
F(000) = 624, l(MoKa) = 0.094 mmÀ1
.
Intensity data
were collected on a Rigaku MERCURY CCD with
graphite monochromated MoKa radiation (k =
0.71070 A) by using x–2h scan mode in the range of
5. InBr3: (a) Bandini, M.; Melchiorre, P.; Melloni, A.;
Umani-Ronchi, A. Synthesis 2002, 1110; InCl3: (b) Yadav,
J. S.; Abraham, S.; Reddy, B. V. S.; Sabitha, G. Synthesis
2001, 2165; Yb(OTf)3 in ScCO2: (c) Komoto, I.; Koba-
yashi, S. J. Org. Chem. 2004, 69, 680; Yb(OTf)3: (d)
Harrington, P. E.; Kerr, M. A. Synlett 1996, 1047; SmI3:
(e) Zhan, Z.-P.; Yang, R.-F.; Lang, K. Tetrahedron Lett.
2005, 46, 3859; CeCl3Æ7H2O–NaI–SiO2: (f) Bartoli, G.;
Bosco, M.; Giuli, S.; Giuliani, A.; Lucarelli, L.; Marcan-
toni, E.; Sambri, L.; Torregiani, E. J. Org. Chem. 2005, 70,
1941; Aluminium dodecyl sulfate trihydrate Al(DS)3]Æ
3H2O (g) Firouzabadi, H.; Iranpoor, N.; Nowrouzi, F.
˚
3.11 < h < 25.34ꢁ. Out of 2675 unique reflections measured
2146 reflections with I > 2r(I) were used in the refinement.
The structure was solved by direct methods and refined by
full-matrix least-squares on F2 using SHELXL-97.13 Non-
hydrogen atoms were refined with anisotropic displace-
ment parameters. The final refinement was converged to
R = 0.0633 and xR = 0.1261.
13. Sheldrick, G. M. SHELXL97: Program for Crystal Structure
Refinement from Refraction Data; University of Gottingen:
Germany, 1997.