Wei Lu et al.
COMMUNICATIONS
(Z)-2-Pentylidene-1,4-diphenyl-3-tosyl-1,2,3,4-tetrahydro-
pyrimidine (4eaa): white solid; mp 95.4–95.68C; 1H NMR
(500 MHz, CDCl3): d=7.84 (d, J=8.0 Hz, 2H), 7.47 (d, J=
7.0 Hz, 2H), 7.35–7.30 (m, 4H), 7.27–7.25 (m, 1H), 7.21 (d,
J=7.5 Hz, 2H), 7.17 (d, J=8.0 Hz, 2H), 7.10 (t, 7.5 Hz,
1H), 6.06 (d, J=8.0 Hz, 1H), 5.55 (d, J=5.5 Hz, 1H), 5.04
(dd, J=8.0, 6.5 Hz, 1H), 4.54 (dd, J=8.0, 5.5 Hz, 1H), 2.35
(s, 3H), 1.92–1.89 (m, 2H), 0.91–0.86 (m, 2H), 0.81–0.75 (m,
1H), 0.63 (t, J=7.3 Hz, 3H), 0.35–0.28 (m, 1H); 13C NMR
(125 MHz, CDCl3): d=144.0, 143.4, 140.0, 136.3, 130.3,
129.9, 129.4, 129.0, 128.6, 128.0, 127.7, 124.0, 122.5, 119.2,
96.5, 57.8, 31.1, 26.7, 22.2, 21.5, 13.8; IR (KBr): n=3061,
2921, 2852, 1676, 1636, 1597, 1492, 1341, 1166, 1150, 1080,
1026, 937, 816, 703 cmÀ1; MS (ESI): m/z=459.3 ([M+H]+);
HR-MS (ESI): m/z=481.1932, calcd. for C28H30N2O2SNa
[M+Na]+: 481.1920.
[5] a) M. Alajarꢃn, B. Bonillo, M.-M. Ortꢃn, P. Sꢄnchez-An-
drada, ꢅ. Vidal, Org. Lett. 2006, 8, 5645–5648; b) M.
Alajarꢃn, M.-M. Ortꢃn, P. Sꢄnchez-Andrada, ꢅ. Vidal,
J. Org. Chem. 2006, 71, 8126–8139; c) K.-W. Lee, N.
Horowitz, J. Ware, L. A. Singer, J. Am. Chem. Soc.
1977, 99, 2622–2627; d) M. A. Walters, J. Am. Chem.
Soc. 1994, 116, 11618–11619.
[6] a) S. L. Cui, X. F. Lin, Y. G. Wang, Org. Lett. 2006, 8,
4517–4520; b) S. L. Cui, J. Wang, Y. G. Wang, Org.
Lett. 2007, 9, 5023–5025; c) S. L. Cui, J. Wang, Y. G.
Wang, Org. Lett. 2008, 10, 1267–1269; d) S. L. Cui, J.
Wang, Y. G. Wang, Tetrahedron 2008, 64, 487–492.
[7] a) I. Bae, H. Han, S. Chang, J. Am. Chem. Soc. 2005,
127, 2038–2039; b) S. H. Cho, E. J. Yoo, I. Bae, S.
Chang, J. Am. Chem. Soc. 2005, 127, 16046–16047;
c) E. J. Yoo, I. Bae, S. H. Cho, H. Han, S. Chang, Org.
Lett. 2006, 8, 1347–1350; d) M. P. Cassidy, J. Raushel,
V. V. Fokin, Angew. Chem. 2006, 118, 3226–3229;
Angew. Chem. Int. Ed. 2006, 45, 3154–3157; e) M.
Whiting, V. V. Fokin, Angew. Chem. 2006, 118, 3229–
3233; Angew. Chem. Int. Ed. 2006, 45, 3157–3161;
f) E. J. Yoo, S. Chang, Org. Lett. 2008, 10, 1163–1166;
g) E. J. Yoo, M. Ahlquist, I. Bae, K. B. Sharpless, V. V.
Fokin, S. Chang, J. Org. Chem. 2008, 73, 5520–5528;
h) S. H. Cho, S. Chang, Angew. Chem. 2008, 120, 2878–
2881; Angew. Chem. Int. Ed. 2008, 47, 2836–2839;
i) S. H. Cho, S. Chang, Angew. Chem. 2007, 119, 1929–
1932; Angew. Chem. Int. Ed. 2007, 46, 1897–1900.
[8] S. H. Kim, D. Y. Jung, S. Chang, J. Org. Chem. 2007, 72,
9769–9771.
Acknowledgements
The authors gratefully acknowledge the financial support of
the National Natural Science Foundation of China (No.
20872128).
References
[1] For a recent review, see: H. Perst, Science of Synthesis
Thieme, Stuttgart, Vol. 23, 2006, pp 781–897.
[2] a) K. Llamas, M. Owens, R. L. Blakeley, B. Zerner, J.
Am. Chem. Soc. 1986, 108, 5543–5548; b) I. Bae, H.
Han, S. Chang, J. Am. Chem. Soc. 2005, 127, 2038–
2039; c) F. F. Fleming, G. Q. Wei, Z. Y. Zhang, O. W.
Steward, Org. Lett. 2006, 8, 4903–4906.
[9] It was reported that azetidin-2-imines are highly stable
under acidic conditions (see Ref.[7e]
[10] CCDC 727476 and CCDC 727477 contain the supple-
mentary crystallographic data for compounds 4aaa and
5aaa, respectively. These data can be obtained free of
charge from The Cambridge Crystallographic Data
[3] a) L. De Vries, J. Org. Chem. 1973, 38, 4357–4362;
b) G. A. Russell, P. Chen, C. F. Yao, B. H. Kim, J. Am.
Chem. Soc. 1995, 117, 5967–5972; c) S. S. Kim, B. Liu,
C. H. Park, K. H. Lee, J. Org. Chem. 1998, 63, 1571–
1573; d) M. Alajarꢃn, A. Vidal, M.-M. Ortꢃn, Org.
Biomol. Chem. 2003, 1, 4282–4292.
[4] a) L. A. Singer, G. A. Davis, J. Am. Chem. Soc. 1967,
89, 598–605; b) A. Dondoni, A. Battaglia, F. Bernardi,
P. Giorgianni, J. Org. Chem. 1980, 45, 3773–3778; c) M.
Alajarꢃn, B. Bonillo, P. Sꢄnchez-Andrada, ꢅ. Vidal, D.
Bautista, J. Org. Chem. 2007, 72, 5863–5866;
d) W. M. F. Fabian, R. Janoschek, J. Am. Chem. Soc.
1997, 119, 4253–4257; e) J. L. Alonso-Gꢆmez, Y. Pazos,
A. Navarro-Vꢄzquez, J. Lugtenburg, M. M. Cid, Org.
Lett. 2005, 7, 3773–3776; f) M. Alajarꢃn, M.-M. Ortꢃn,
P. Sꢄnchez-Andrada, A. Vidal, D. Bautista, Org. Lett.
2005, 7, 5281–5284; g) M. Alajarꢃn, A. Vidal, F. Tovar,
A. Arrieta, B. Lecea, F. P. Cossꢃo, Chem. Eur. J. 1999,
5, 1106–1117.
[11] For a recent review on the synthesis of pyrimidines,
see: a) M. D. Hill, M. Movassaghi, Chem. Eur. J. 2008,
14, 6836–6844. For recent examples for the synthesis of
pyrimidines and pyrimidine-containing libraries, see:
b) J. Vicario, D. Aparicio, F. Palacios, J. Org. Chem.
2009, 74, 452–455; c) J. Cesar, J. Comb. Chem. 2005, 7,
517–519; d) S. R. Klutchko, H. Zhou, R. T. Winters,
T. P. Tran, A. J. Bridges, I. W. Althaus, D. M. Amato,
W. L. Elliott, P. A. Ellis, M. A. Meade, B. J. Roberts,
D. W. Fry, A. J. Gonzales, P. J. Harvey, J. M. Nelson, V.
Sherwood, H.-K. Han, G. Pace, J. B. Smaill, W. A.
Denny, H. D. H. Showalter, J. Med. Chem. 2006, 49,
1475–1485; e) A. Contini, E. Erba, P. Trimarco, Tetra-
hedron 2008, 64, 11067–11073.
1772
ꢁ 2009 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Adv. Synth. Catal. 2009, 351, 1768 – 1772