Angewandte
Chemie
2005, 44,6990 – 6993; b) S. Ma,S. Yu,Z. Gu, Angew. Chem. 2006,
Experimental Section
118,206 – 209; Angew. Chem. Int. Ed. 2006, 45,200 – 203.
[12] PtCl2 showed similar catalytic activity to that of AuCl towards
the reaction. However,the reaction of 1g in the presence of
PtCl2,instead of AuCl,did not proceed at all.
[13] a) K. Sugoh,H. Kuniyasu,T. Sugae,A. Ohtaka,Y. Takai,A.
Tanaka,C. Machino,N. Kambe,H. Kurosawa, J. Am. Chem. Soc.
2001, 123,5108 – 5109; b) M. Toyofuku,S.-I. Fujiwara,T. Shin-
ike,H. Kuniyasu,N. Kambe, J. Am. Chem. Soc. 2005, 127,9706 –
9707.
Substrate 1 (0.25 mmol) in toluene (0.5 mL) was added to AuCl
(1.16 mg,0.005 mmol) in toluene (0.75 mL) in a pressure vial under
an argon atmosphere. After the reaction mixture had been stirred at
258C for 2 h,it was filtered through a short column of silica gel by
using ethyl acetate as eluent. The crude product was purified by silica-
gel column chromatography with hexane/ethyl acetate as eluent to
give 2.
2a: IR (neat): n˜ = 3060,2959,2929,2871,2817,1573,1460,1436,
À1
1093,760,732 cm
;
1H NMR (600 MHz,CDCl 3): d = 1.01 (t, J =
[14] M. C. Willis,D. Taylor,A. T. Gillmore, Org. Lett. 2004, 6,4755 –
4757.
7.2 Hz,3H),1.75 (m,2H),2.93 (t,
4.46 (s,2H),7.27 (ddd, J = 8.4,7.2,1.2 Hz,1H),7.35 (ddd, J = 8.4,7.2,
1.2 Hz,1H),7.76 ppm (m,1H),7.79 (m,1H);
13C NMR (150 MHz,
CDCl3): d = 13.82,24.99,30.47,57.76,65.62,121.75,121.99,123.71,
J = 7.8 Hz,2H),3.38 (s,3H),
[15] For a review,see: a) C. M. Rayner,M. A. Graham, Sci. Synth.
2001, 10,155 – 184; b) T. Y. Zhang,J. OꢁToole,C. S. Proctor,
Sulfur Rep. 1999, 22,1 – 47; c) E. T. Pelkey, Prog. Heterocycl.
Chem. 1999, 11,102 – 123; d) C. Bianchini,A. Meli, Synlett 1997,
643 – 649.
124.07,127.60,138.18,140.10,145.28 ppm; HRMS (ESI):
m/z calcd
for C13H16OS: 243.0814 [M+Na]+; found: 243.0815.
Received: March 24,2006
Published online: June 12,2006
Keywords: cyclization · gold · homogeneous catalysis ·
.
sulfur heterocycles · synthetic methods
[1] C. D. Jones,M. G. Jevnikar,A. J. Pike,M. K. Peters,L. J. Black,
A. R. Thompson,J. F. Falcone,J. A. Clemens, J. Med. Chem.
1984, 27,1057 – 1066.
[2] M. Raga,C. Palacin,J. M. Castello,J. A. Ortiz,M. R. Cuberes,
M. Moreno-Manas, Eur. J. Med. Chem. 1986, 21,329 – 332.
[3] Acylation: a) C. Hansch,H. G. Lindwall, J. Org. Chem. 1945, 10,
381 – 385; b) K. C. Lee,B. S. Moon,J. H. Lee,K.-H. Chung,J. A.
Katzenellenbogen,D. Y. Chi, Bioorg. Med. Chem. 2003, 11,
3649 – 3658. Halogenation: c) J. Szmuszkovicz,E. J. Modest, J.
Am. Chem. Soc. 1950, 72,571 – 577.
[4] a) A. R. Katritzky,S. N. Denisenko,D. C. Oniciu,I. Ghiviriga, J.
Org. Chem. 1998, 63,3450 – 3453; b) S. Kamila,C. Mukherjee,
S. S. Mondal,A. De, Tetrahedron 2003, 59,1339 – 1348; c) T. K.
Pradhan,S. C. Ghosh,A. De, ARKIVOC 2003, 9,158 – 173.
[5] For reviews,see: a) G. Battistuzzi,S. Cacchi,G. Fabrizi, Eur. J.
Org. Chem. 2002,2671 – 2681; b) S. Cacchi,G. Fabrizi,A.
Goggiomani, Heterocycles 2002, 56,613 – 632; c) G. Balme,D.
Bouyssi,T. Lomberget,N. Monteiro, Synthesis 2003, 14,2115 –
2134; d) I. Nakamura,Y. Yamamoto, Chem. Rev. 2004, 104,
2127 – 2198; e) G. Zeni,R. C. Larock, Chem. Rev. 2004, 104,
2285 – 2309. For a recent report,see f) A. S. K. Hashmi,T. M.
Frost,J. W. Bats, Org. Lett. 2001, 3,3769 – 3771.
[6] A. M. Malte,C. E. Castro, J. Am. Chem. Soc. 1967, 89,6770.
[7] For examples of palladium(0)-catalyzed endo cyclization,see:
a) S. Cacchi,G. Fabrizi,L. Moro, Synlett 1998,741 – 745; b) N.
Monterio,G. Balme, Synlett 1998,746 – 747; c) S. Cacchi,G.
Fabrizi,P. Pace, J. Org. Chem. 1998, 63,1001 – 1011; d) A.
Arcadi,S. Cacchi,M. Del Rosario,G. Fabrizi,F. Marinelli,
J.
Org. Chem. 1996, 61,9280 – 9288. For PtCl 2-catalyzed cycliza-
tions,see: e) A. Fꢀrstner,H. Szillat,F. Stelzer, J. Am. Chem. Soc.
2000, 122,6785 – 6786; f) A. Fꢀrstner,F. Stelzer,H. Szillat,
Am. Chem. Soc. 2001, 123,11863 – 11869.
J.
[8] S. Cacchi,G. Fabrizi,L. Moro, Tetrahedron Lett. 1998, 39,5101 –
5104.
[9] T. Shimada,I. Nakamura,Y. Yamamoto, J. Am. Chem. Soc. 2004,
126,10546 – 10547.
[10] a) I. Nakamura,Y. Mizushima,Y. Yamamoto, J. Am. Chem. Soc.
2005, 127,15022 – 15023; b) A. Fꢀrstner,P. W. Davies, J. Am.
Chem. Soc. 2005, 127,15024 – 15025.
[11] For reviews on gold-catalyzed reaction,see: a) A. S. K. Hashmi,
Angew. Chem. 2005, 117,7150 – 7154; Angew. Chem. Int. Ed.
Angew. Chem. Int. Ed. 2006, 45, 4473 –4475
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