1612
A. V. Narsaiah et al.
PAPER
EIMS: m/z (%) = 328 (M+ + 1, 70), 297 (10), 278 (12), 253 (10), 223
(10), 221 (100), 191 (12), 190 (20), 175 (10), 159 (10), 151 (10),
130 (10).
IR (neat): 3409, 3075, 3018, 2924, 1639, 1601, 1505, 1321, 992,
912, 747, 691 cm–1.
1H NMR (CDCl3): d = 1.00–1.28 (m, 5 H), 1.40–1.56 (m, 1 H),
2.12–2.38 (m, 2 H), 3.22 (dd, J = 5.1, 12.9 Hz, 1 H), 3.50 (br s, 1
H), 5.00–5.08 (m, 2 H), 5.72–5.84 (m, 1 H), 6.56 (d, J = 8.7 Hz, 2
H), 6.62 (t, J = 7.2 Hz, 1 H), 7.12 (dt, J = 7.2, 8.7 Hz, 2 H).
N-[1-(4-Isopropylphenyl)but-3-enyl]-4-methylbenzeneamine
(4c)
Brown liquid.
IR (neat): 3405, 3015, 2962, 2926, 2869, 2730, 1702, 1611, 1577,
1518, 1461, 1421, 1305, 1265, 1213, 1171, 1108, 1054, 994, 918,
830, 727 cm–1.
1H NMR (CDCl3): d = 1.20 (s, 6 H), 2.18 (s, 3 H), 2.45–2.65 (m, 2
H), 2.85–3.05 (m, 1 H), 4.25–4.35 (m, 1 H), 5.20 (t, J = 6.5 Hz, 2
H), 5.68–5.78 (m, 1 H), 6.35 (d, J = 6.5 Hz, 2 H), 6.85 (d, J = 6.5
Hz, 2 H), 7.10 (d, J = 6.5 Hz, 2 H), 7.25 (d, J = 6.5 Hz, 1 H), 7.40
(d, J = 6.5 Hz, 1 H).
Acknowledgment
J.K.K. and P.N.R. are thankful to CSIR New Delhi for providing
fellowships.
References
(1) (a) Neipp, C. E.; Humpherey, J. M.; Martin, S. F. J. Org.
Chem. 2001, 66, 531. (b) Gao, Y.; Sato, F. J. Org. Chem.
1995, 60, 8136.
EIMS: m/z (%) = 280 (M+ + 1, 100), 279 (15), 262 (20), 238 (35),
223 (10), 223 (10), 174 (10), 173 (20), 158 (10), 138 (10), 109 (10).
(2) (a) Yamasaki, S.; Fujii, K.; Wada, R.; Kanai, M.; Shibasaki,
M. J. Am. Chem. Soc. 2002, 124, 6536. (b) Chan, T. H.; Lu,
W. Tetrahedron Lett. 1998, 39, 8605. (c) Akiyama, T.;
Iwai, J. Synlett 1998, 273. (d) Keck, G. E.; Enholm, E. J.
J. Org. Chem. 1985, 50, 146. (e) Akiyama, T.; Iwai, J.;
Onuma, Y.; Kagoshima, H. Chem. Commun. 1999, 2191.
(f) Hopkins, C. D.; Malinakova, H. C. Org. Lett. 2006, 8,
5971.
N-[1-(Furan-2-yl)but-3-enyl]-4-methylbenzeneamine (4f)
Yellow syrup.
IR (neat): 3415, 2924, 2859, 1618, 1518, 1442, 1300, 1260, 1218,
1183, 1150, 1074, 1005, 920, 808, 737 cm–1.
1H NMR (CDCl3): d = 2.21 (s, 3 H), 2.62 (t, J = 6.0 Hz, 2 H), 4.49
(t, J = 6.0 Hz, 1 H), 5.12 (dd, J = 10.5, 6.0 Hz, 2 H), 5.60–5.80 (m,
1 H), 6.08 (s, 1 H), 6.22 (s, 1 H), 6.45 (d, J = 6.5 Hz, 2 H), 6.89 (d,
J = 6.5 Hz, 2 H), 7.31 (s, 1 H).
(3) (a) Phukan, P. J. Org. Chem. 2004, 69, 4005. (b) Das, B.;
Lakshmi, G. S.; Suneel, K.; Kanth, B. S. Tetrahedron Lett.
2008, 49, 7209.
EIMS: m/z (%) = 228 (M+ + 1, 60), 226 (M+ – 1, 100), 190 (10), 158
(4) (a) Kalita, P. K.; Phukan, P. Tetrahedron Lett. 2008, 49,
5495. (b) Akiyama, T.; Onuma, Y. J. Chem. Soc., Perkin
Trans. 1 2002, 1157. (c) Shibata, I.; Nose, K.; Sakamoto,
K.; Yasuda, M.; Baba, A. J. Org. Chem. 2004, 69, 2185.
(d) Pasunooti, K. K.; Leow, M. L.; Chalam, S. V.; Gorityala,
B. K.; Liu, X. W. Tetrahedron Lett. 2009, 50, 2979.
(5) (a) Kobayashi, S.; Busujima, T.; Nagayama, S. Chem.
Commun. 1998, 19. (b) Aspinall, H. C.; Bissett, J. S.;
Greeves, N.; Levin, D. Tetrahedron Lett. 2002, 43, 323.
(c) Ollevier, T.; Ba, T. Tetrahedron Lett. 2003, 44, 9003.
(6) Yadav, J. S.; Reddy, B. V. S.; Raju, A. K. Synthesis 2003,
883.
(45), 144 (25), 102 (20).
4-[1-(p-Toluidino)but-3-enyl]benzonitrile (4g)
Light-colored thick syrup.
IR (neat): 3401, 2924, 2855, 2227, 1615, 1519, 1460, 1411, 1300,
1265, 1112, 993, 921, 834, 809, 772 cm–1.
1H NMR (CDCl3): d = 2.20 (s, 3 H), 2.45 (q, J = 5.0 Hz, 1 H), 2.55–
2.65 (m, 1 H), 4.33–4.41 (m, 1 H), 5.15–5.25 (m, 2 H), 5.65–5.80
(m, 1 H), 6.28 (d, J = 6.5 Hz, 2 H), 6.82 (d, J = 6.5 Hz, 2 H), 7.48
(d, J = 6.5 Hz, 2 H), 7.60 (d, J = 6.5 Hz, 2 H).
EIMS: m/z (%) = 263 (M+ + 1, 100), 261 (M+, 10) 247 (10), 225
(7) (a) Yadav, J. S.; Reddy, B. V. S.; Reddy, R. S. R.; Rao, M.
S. Tetrahedron Lett. 2002, 43, 6245. (b) Shen, W.; Wang,
L. M.; Feng, J. J.; Tian, H. Tetrahedron Lett. 2008, 49,
4047. (c) Ella-Menye, J. R.; Dobbs, W.; Billet, M.; Klotz, P.;
Mann, A. Tetrahedron Lett. 2005, 46, 1897. (d) Nagarapu,
L.; Paparaju, V.; Pathuri, G.; Kantevari, S.; Pakkiru, R. R.;
Kamalla, R. J. Mol. Catal. A: Chem. 2007, 267, 53.
(8) (a) Das, B.; Narayana, K. L.; Kanth, B. R.; Rao, B. R.
Tetrahedron Lett. 2006, 47, 9103. (b) Das, B.; Kanth, B. R.;
Thirupathi, P.; Rao, B. V. Tetrahedron Lett. 2006, 47, 5041.
(c) Yin, Y.; Zhao, G.; Li, G. L. Tetrahedron 2005, 61,
12042. (d) Tirupathi, P.; Kim, S. S. Tetrahedron 2009, 65,
5168.
(10), 210 (10), 182 (20), 168 (10), 149 (15), 144 (10), 108 (25).
N-(1-Phenylbut-3-enyl)cyclohexaneamine (4l)
Brown syrup.
IR (neat): 3423, 3069, 3029, 2925, 2854, 1642, 1492, 1455, 1376,
1261, 1195, 1048, 915, 871, 800, 757, 701, 608 cm–1.
1H NMR (CDCl3): d = 0.78–0.98 (m, 2 H), 1.22–1.42 (m, 7 H), 1.65
(s, 1 H), 1.80 (br s, 1 H, NH), 2.05 (s, 1 H), 2.40–2.55 (m, 2 H), 4.70
(t, J = 6.0 Hz, 1 H), 5.15 (t, J = 6.0 Hz, 2 H), 5.70–5.85 (m, 1 H),
7.25–7.40 (m, 5 H).
N-(1-Cyclohexylbut-3-enyl)benzeneamine (4n)
(9) Review: Ghosh, R.; Maiti, S. J. Mol. Catal. A: Chem. 2007,
264, 1.
Yellow thick syrup.
Synthesis 2010, No. 10, 1609–1612 © Thieme Stuttgart · New York