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LETTER
(4) (a) Stetter, H. Angew. Chem., Int. Ed. Engl. 1976, 15, 639;
Angew. Chem.; 1976, 88, 695. (b) Stetter, H.; Kuhlmann, H.
Org. React. (N.Y.) 1991, 40, 407.
(10) For recent examples, see: (a) Christopher, R. J.; Pantos, G.
D.; Angus, J. M.; Martin, D. S. Angew. Chem. Int. Ed. 2009,
48, 7391; Angew. Chem. 2009, 121, 7527. (b) Sylvain, B.;
Ross, W. C.; David, B. B. Org. Lett. 2009, 11, 305.
(11) (a) Sánchez-Larios, E.; Gravel, M. J. Org. Chem. 2009, 74,
7536. (b) Sánchez-Larios, E.; Holmes, J. M.; Daschner,
C. L.; Gravel, M. Org. Lett. 2010, 12, 5772.
(12) Sun, F.-G.; Huang, X.-L.; Ye, S. J. Org. Chem. 2010, 75,
273.
(13) Xiao, F.; Lancelot, J. C.; Prunier, H.; Rault, S. J. Heterocycl.
Chem. 1996, 33, 2007.
(14) Abderhamid, A. O.; Negm, A. M.; Abbas, I. M. J. Prakt.
Chem. 1989, 331, 31.
(15) (a) Gewald, K. Chem. Ber. 1966, 99, 1002. (b) Jun, J. G.
Bull. Korean Chem. Soc. 1996, 17, 676.
(16) Watanuki, S.; Sakamoto, S.; Harada, H.; Kikuchi, K.;
Kuramochi, T.; Kawaguchi, K.; Okazaki, T.; Tsukamoto, S.
Heterocycles 2004, 62, 127.
(5) (a) Hachisu, Y.; Bode, J. W.; Suzuki, K. J. Am. Chem. Soc.
2003, 125, 8432. (b) Burstein, C.; Glorius, F. Angew. Chem.
Int. Ed. 2004, 43, 6205; Angew. Chem. 2004, 116, 6331.
(c) Enders, D.; Niemeier, O.; Balensiefer, T. Angew. Chem.
Int. Ed. 2006, 45, 1463; Angew. Chem. 2006, 118, 1491.
(d) Burstein, C.; Tschan, S.; Xie, X.; Glorius, F. Synthesis
2006, 2418. (e) Takikawa, H.; Hachisu, Y.; Bode, J. W.;
Suzuki, K. Angew. Chem. Int. Ed. 2006, 45, 3492; Angew.
Chem. 2006, 118, 3572. (f) Li, Y.; Feng, Z.; You, S.-L.
Chem. Commun. 2008, 226. (g) Hirano, K.; Piel, I.; Glorius,
F. Adv. Synth. Catal. 2008, 350, 984.
(6) (a) Liu, Y.-K.; Li, R.; Yue, L.; Li, B.-J.; Chen, Y.-C.; Wu,
Y.; Ding, L.-S. Org. Lett. 2006, 8, 1521. (b) Yadav, L. D.
S.; Rai, V. K.; Singh, S.; Singh, P. Tetrahedron Lett. 2010,
51, 1657.
(7) Mattson, A. E.; Zuhl, A. M.; Reynolds, T. E.; Scheidt, K. A.
(17) Heravi, M. M.; Tehrani, M. H.; Bakhtiari, K.; Oskooie, H. A.
J. Chem. Res. 2006, 9, 561.
J. Am. Chem. Soc. 2006, 128, 4932.
(8) (a) Murry, J. A.; Franz, D. E.; Soheil, A.; Tillyer, R. E.;
Grabowski, J. J.; Reider, P. J. J. Am. Chem. Soc. 2001, 123,
9696. (b) Mennen, S. M.; Gipson, J. D.; Kim, Y. R.; Miller,
S. J. J. Am. Chem. Soc. 2005, 127, 1654. (c) Li, G.-Q.; Dai,
L.-X.; You, S.-L. Chem. Commun. 2007, 852.
(9) For reviews on cascade reactions, see: (a) Tietze, L. F.
Chem. Rev. 1996, 96, 115. (b) Fogg, D. E.; dos Santos, E. N.
Coord. Chem. Rev. 2004, 248, 2365. (c) Chapman, C. J.;
Frost, C. G. Synthesis 2007, 1. (d) Enders, D.; Grondal, C.;
Hüttl, M. R. M. Angew. Chem. Int. Ed. 2007, 46, 1570;
Angew. Chem. 2007, 119, 1590. (e) Tietze, L. F.; Brasche,
G.; Gericke, K. Domino Reactions in Organic Synthesis;
Wiley-VCH: Weinheim, 2006.
(18) General procedure for the synthesis of 4,5-disubstituted 2-
aminofuran-3-carbonitriles 3: A flame-dried, round-bottom
flask was charged with thiazolium salt 4c (0.5 mmol),
aromatic aldehyde 1 (1.0 mmol), acylidenemalononitrile 2
(1.0 mmol), and EtOH (5 mL) under a positive pressure of
nitrogen, followed by addition of t-BuOK (1.0 mmol).
The resulting solution was stirred for 0.5–2 h at r.t. After
completion of the reaction (monitored by TLC), the reaction
mixture was concentrated under reduced pressure. The
residue was purified by column chromatography on silica
gel (petroleum ether–EtOAc, 6:1) to afford the product 3.
Synlett 2011, No. 8, 1133–1136 © Thieme Stuttgart · New York