4
48
S. Yuan, Z. Li, and L. Xu
Vol 47
in vacuo. The pure products were obtained by flash chromatogra-
phy on silica gel eluting with petroleum ether/EtOAc (1:4, V:V),
[4] Cooney, J. V.; McEwen, W. E. J Org Chem 1981, 46,
2570.
1
13
[
[
5] Lee, D.; Swager, T. M. J Am Chem Soc 2003, 125, 6870.
6] Peschko, C.; Winklhofer, C.; Terpin, A.; Steglich, W. Syn-
and identified by IR, H-, C-NMR, and HRMS.
-Octyl-2,5-dimethylpyrrole (3i). IR: 3035.2, 2983.5,
1
593.6, 1466.5, 1340.2, 976.3, 810.3 cm ; H-NMR (CDCl ,
ꢁ
1
1
thesis 2006, 3048.
1
3
3
[
7] Sanmadjar, S.; Besker, F. F.; Banik, B. K. Heterocycles
00 MHz) d: 5.76 (s, 2H, 2ꢂCH), 3.73 (t, J ¼ 7.8, 2H,
2
001, 55, 1019.
CH
1
2
N), 2.19 (s, 6H, 2ꢂCH
3 2
), 1.68–1.74 (m, 2H, CH ), 1.33–
13
[8] Song, G.; Wang, B.; Wang, G.; Kang, Y.; Yang, T.; Yang,
L. Synth Commun 2005, 35, 1051.
9] Banik, B. K.; Samajdar, S.; Bnik, I. J Org Chem 2004, 69,
.45 (m, 12H, 6ꢂCH
2
), 0.97 (t, J ¼ 7.6, 3H, CH
3
); C-NMR
(
CDCl , 75 MHz) d: 12.71, 14.21, 24.62, 30.50, 31.10, 31.59,
3
[
3
C
2.30, 35.73, 47.82, 107.66, 129.84; HRMS: calcd for
27N: 209.3707, found: 209.3695.
213.
14
H
In conclusion, it was very appropriate that macroporous
[
10] Ballini, R.; Barboni, L.; Bosica, G.; Petrini, M. Synlett
2
000, 391.
strongly acidic styrol resin (D001) was employed as catalyst
for the Paal-Knorr reaction. Various amines underwent the ear-
lier reaction with 2,5-hexanedione to produce different substi-
tuted pyrroles in high yields. The majority of reactions were
carried out at room temperature and a shorter period of time
[
[
11] Balme, G. Angew Chem Int Ed 2004, 43, 6238.
12] Bianchi, I.; Forlani, R.; Minetto, G.; Peretto, I.; Regalia, N.;
Taddei, M.; Raveglia, L. F. J Comb Chem 2006, 8, 491.
13] Banik, B. K.; Banik, I.; Renteria, M.; Dasgupta, S. K. Tet-
[
rahedron Lett 2005, 46, 2643.
(0.5–2.5 h). The reaction conditions are very mild, and no sol-
vent was used to carry out the reaction.
[14] Chen, J.; Wu, H.; Zheng, Z.; Jin, C.; Zhang, X.; Su, W.
Tetrahedron Lett 2006, 47, 5383.
[
15] Wang, B.; Gu, Y.; Luo, C.; Yang, T.; Yang, L.; Suo, J. Tet-
rahedron Lett 2004, 45, 3417.
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Journal of Heterocyclic Chemistry
DOI 10.1002/jhet