L.-P. Sun et al. / Tetrahedron 60 (2004) 10983–10992
10991
3789–3799. (c) Owa, T.; Okauchi, T.; Yoshimatsu, K.; Sugi,
N. H.; Ozawa, Y.; Nagasu, T.; Koyanagi, N.; Okabe, T.; Kitoh,
K.; Yoshino, H. 2000, Bioorg. Med. Chem. Lett. 10,
1223–1226.
L. L.; McGuire, M. A.; Botha, G. Tetrahedron Lett. 1998, 39,
9347–9350. (o) van Esseveldt, B. C. J.; van Delft, F. L.; de
Gelder, R.; Rutjes, F.P.J.T. Org. Lett. 2003, 5, 1717–1720. For
a
microwave-assisted solid-phase indole synthesis, see:
7. (a) Ottoni, O.; Cruz, R.; Krammer, N. H. Tetrahedron Lett.
1999, 40, 1117–1120. (b) Pelkey, E. T.; Gribble, G. W.
Synthesis 1999, 1117–1122. (c) Jiang, J.; Gribble, G. W.
Tetrahedron Lett. 2002, 43, 4115–4117.
(p) Dai, W.-M.; Guo, D.-S.; Sun, L.-P.; Huang, X.-H. Org.
Lett. 2003, 5, 2919–2922. Also see: (q) Takeda, A.; Kamijo,
S.; Yamamoto, Y. J. Am. Chem. Soc. 2000, 122, 5662–5663.
16. For Pd(0)–Cu(I)-catalyzed cyclization of 2-alkynylanilines,
see: (a) Sakamoto, T.; Kondo, Y.; Iwashita, S.; Nagano, T.;
Yamanaka, H. Chem. Pharm. Bull. 1988, 36, 1305–1308.
(b) Xu, L.; Lewis, I. R.; Davidsen, S. K.; Summers, J. B.
Tetrahedron Lett. 1998, 39, 5159–5162. Synthesis on solid
support, see: (c) Zhang, H.-C.; Brumfield, K. K.; Jaroskova, L.;
Maryanoff, B. E. Tetrahedron Lett. 1998, 39, 4449–4452.
(d) Zhang, H.-C.; Ye, H.; Moretto, A. F.; Brumfield, K. K.;
Maryanoff, B. E. Org. Lett. 2000, 2, 89–92.
8. Gribble, G. W. J. Chem. Soc., Perkin Trans. 1 2000,
1045–1075. Gribble, G. W. Contemp. Org. Synth. 1994,
145–172.
9. (a) Ockenden, D. W.; Schofield, K. J. J. Chem. Soc. 1957,
3175. (b) Atkinson, C. M.; Simpson, J. C. E.; Taylor, A.
J. Chem. Soc. 1945, 530. (c) Grandberg, I. I.; Belyaeva, L. D.;
Dmitriev, L. D.; Dmitriev, L. B. Khim. Geterotsikl. Soed.
(Russ) 1973, 37, 37. (d) Singer, H.; Shive, W. J. Org. Chem.
1957, 22, 84–85. (e) Parmerter, S. M.; Cook, G.; Dixon, W. B.
J. Am. Chem. Soc. 1958, 80, 4621–4622. (f) Szczepankiewicz,
B. G.; Heathcock, C. H. Tetrahedron 1997, 53, 8853–8870.
10. (a) Bergman, J.; Sand, P.; Tilstam, U. Tetrahedron Lett. 1983,
24, 3665–3668. (b) Bergman, J.; Sand, P. Tetrahedron 1990,
46, 6085–6112. (c) Melhado, L. L.; Brodsky, J. L. J. Org.
Chem. 1988, 53, 3852–3855. (d) Kato, K.; Ono, M.; Akita, H.
Tetrahedron Lett. 1997, 38, 1805–1808.
17. For Cu(I)-catalyzed cyclization of 2-alkynylanilines, see:
(a) Castro, C. E.; Stephens, R. D. J. Org. Chem. 1963, 28,
2163–2164. (b) Castro, C. E.; Gauhan, E. J.; Owsley, D. C.
J. Org. Chem. 1966, 31, 4071–4078. (c) Villemin, D.; Goussu,
D. Heterocycles 1989, 29, 1255–1261. (d) Kumar, V.; Dority,
A. A.; Bacon, E. R.; Singh, B.; Lesher, G. Y. J. Org. Chem.
1992, 57, 6995–6998. (e) Katritzky, A. R.; Li, J.; Stevens,
C. V. J. Org. Chem. 1995, 60, 3401–3404. (f) Ezquerra, J.;
´ ´
Pedregal, C.; Lamas, C.; Barluenga, J.; Perez, M.; Garcıa--
11. (a) Sutherland, J. K. Chem. Commun. 1997, 325. (b) Pelkey,
E. T.; Gribble, G. W. Tetrahedron Lett. 1997, 38, 5603–5606.
(c) ten Have, R.; van Leusen, A. M. Tetrahedron 1998, 54,
1913–1920. (d) Moskalev, N.; Makosza, M. Tetrahedron Lett.
1999, 40, 5395–5398. (e) Moskalev, N.; Barbasiewicz, M.;
Makosza, M. Tetahedron 2004, 60, 347–358.
´
´
Martın, M. A.; Gonzalez, J. M. J. Org. Chem. 1996, 61,
5804–5812. (g) Soloducho, J. Tetrahedron Lett. 1999, 40,
2429–2430. (h) Cacchi, S.; Fabrizi, G.; Parisi, L. M. Org. Lett.
2003, 5, 3843–3846.
18. For Cu(II)-catalyzed cyclization of 2-alkynylanilines, see:
(a) Saulnier, M. G.; Frennesson, D. B.; Deshpande, M. S.;
Vyas, D. M. Tetrahedron Lett. 1995, 36, 7841–7844.
(b) Hiroya, K.; Itoh, S.; Ozawa, M.; Kanamori, Y.; Sakamoto,
T. Tetrahedron Lett. 2002, 43, 1277–1280. (c) Hiroya, K.;
Itoh, S.; Sakamoto, T. J. Org. Chem. 2004, 69, 1126–1136. For
12. (a) Metal-Catalyzed Cross-Coupling Reactions; Diederich, F.,
Stang, P. J., Eds.; Wiley-VCH: Weinheim, 1998. (b) Tsuji, J.
Palladium Reagents and Catalysts; Wiley: Chichester, 1995.
(c) Li, J. J.; Gribble, G. W. Palladium in Heterocyclic
Chemistry; Pergamon: Amsterdam, 2000.
13. The Sonogashira cross-coupling reaction, see: (a) Sonogashira,
K.; Tohda, Y.; Hagihara, N. 1975, 4467–4470.
(b) Sonogashira, K. In Trost, B. M., Fleming, I., Eds.;
Comprehensive Organic Synthesis; Pergamon: New York,
1991; Vol. 3, pp 521–549. (c) Rossi, R.; Carpita, A.; Bellina, F.
1995, Org. Prep. Proc. Int. 27, 127–160.
a microwave-assisted solid-phase indole synthesis, see
Ref. 15p.
19. For (Et3N)Mo(CO)5-catalyzed cyclization of 2-alkynylani-
lines, see: (a) McDonald, F. E.; Chatterjee, A. K. Tetrahedron
Lett. 1997, 38, 7687–7690. (b) McDonald, F. E. Chem. Eur. J.
1999, 5, 3103–3106.
14. For a recent review on Pd-catalyzed annulation, see: Larock,
R. C. J. Organomet. Chem. 1999, 576, 111–124.
20. Alkoxide-catalyzed cyclization of 2-alkynylanilines, see:
(a) Sakamoto, T.; Kondo, Y.; Yamanaka, H. Heterocycles
1986, 24, 31–32. (b) Sakamoto, T.; Kondo, Y.; Yamanaka, H.
Heterocycles 1986, 24, 1845–1847. (c) Sakamoto, T.; Kondo,
Y.; Iwashita, S.; Yamanaka, H. Chem. Pharm. Bull. 1987, 35,
1823–1828. (d) Sakamoto, T.; Kondo, Y.; Iwashita, S.;
Nagano, T.; Yamanaka, H. Chem. Pharm. Bull. 1988, 36,
1305–1308. (e) Shin, K.; Ogasawara, K. Synlett 1995,
859–860. (f) Kondo, Y.; Kojima, S.; Sakamoto, T. Hetero-
cycles 1996, 43, 2741–2746. (g) Kondo, Y.; Kojima, S.;
Sakamoto, T. J. Org. Chem. 1997, 62, 6507–6511.
(h) Rodriguez, A. L.; Koradin, C.; Dohle, W.; Knochel, P.
Angew. Chem. Int. Ed. 2000, 39, 2488–2490. (i) Dai, W.-M.;
Guo, D.-S.; Sun, L.-P. Tetrahedron Lett. 2001, 42, 5275–5278.
(j) Dai, W.-M.; Sun, L.-P.; Guo, D.-S. Tetrahedron Lett. 2002,
43, 7699–7702. (k) Koradin, C.; Dohle, W.; Rodriguez, A. L.;
Schmid, B.; Knochel, P. Tetrahedron 2003, 59, 1571–1587.
21. TBAF-catalyzed cyclization of 2-alkynylanilines, see:
Yasuhara, A.; Kanamori, Y.; Kaneko, M.; Numata, A.;
Kondo, Y.; Sakamoto, T. J. Chem. Soc., Perkin Trans. 1
1999, 529–534.
15. For Pd(II)-catalyzed cyclization of 2-alkynylanilines, see:
(a) Utimoto, K.; Miwa, H.; Nozaki, H. Tetrahedron Lett. 1981,
22, 4277–4278. (b) Utimoto, K. Pure Appl. Chem. 1983, 55,
1845–1852. (c) Taylor, E. C.; Katz, A. H.; Salgado-Zamore,
H.; McKillop, A. Tetrahedron Lett. 1985, 26, 5963–5966.
(d) Krolski, M. E.; Renaldo, A. F.; Rudisill, D. E.; Stille, J. K.
J. Org. Chem. 1988, 53, 1170–1176. (e) Iritani, K.; Matsubara,
S.; Utimoto, K. Tetrahedron Lett. 1988, 29, 1799–1802.
(f) Arcadi, A.; Cacchi, S.; Marinelli, F. Tetrahedron Lett.
1989, 30, 2581–2584. (g) Rudisill, D.; Stille, J. K. J. Org.
Chem. 1989, 54, 5856–5866. (h) Kondo, Y. K.; Sakamoto, T.;
Yamanaka, H. Hetrocycles 1989, 29, 1013–1016. (i) Fukuda,
Y.; Matsubara, S.; Utimoto, K. J. Org. Chem. 1991, 56,
5812–5816. (j) Jeschke, T.; Wensbo, D.; Annby, U.;
Gronowitz, S.; Cohen, L. Tetrahedron Lett. 1993, 34,
6471–6474. (k) Kondo, Y.; Shiga, N.; Murata, N.; Sakamoto,
T.; Yamanaka, H. Tetrahedron 1994, 50, 11803–11812.
(l) Cacchi, S.; Carnicelli, V.; Marinelli, F. J. Organomet.
Chem. 1994, 475, 289–296. (m) Samizu, K.; Ogasawara, K.
Heterocycles 1995, 41, 1627–1629. (n) Yu, M. S.; de Leon,
22. TMG-catalyzed cyclization of 2-alkynylanilines, see: