6566
H. B. Borate et al. / Tetrahedron Letters 50 (2009) 6562–6566
4. Na, Y.-M.; Le Borgne, M.; Pagniez, F.; Le Baut, G.; Le Pape, P. Eur. J. Med. Chem.
2003, 38, 75.
5. Tiwari, R. K.; Singh, J.; Singh, D.; Verma, A. K.; Chandra, R. Tetrahedron 2005, 61,
9513.
large number of novel indoles and hydroxyindolines with a wide
variety of functional groups.
6. (a) Konosu, T.; Tajima, Y.; Takeda, N.; Miyaoka, T.; Kasahara, M.; Yasuda, H.;
Oida, S. Chem. Pharm. Bull. 1990, 38, 2476; (b) Upadhayaya, R. S.; Jain, S.; Sinha,
N.; Kishore, N.; Chandra, R.; Arora, S. K. Eur. J. Med. Chem. 2004, 39, 579; (c)
Santamaria, A.; Moreno-Mañas, M.; Pleixats, R. ARKIVOC 2007, iv, 234; (d)
Lebouvier, N.; Giraud, F.; Corbin, T.; Na, Y. M.; Le Baut, G.; Marchanda, P.; Le
Borgnea, M. Tetrahedron Lett. 2006, 47, 6479.
Acknowledgments
S.R.M. and S.P.S. thank CSIR, New Delhi, for the Grant of Senior
Research Fellowships. We thank Dr. S. P. Chavan for helpful
discussions.
7. (a) Gewald, K. Chem. Ber. 1965, 98, 3571; (b) Gewald, K.; Scmnke, E.; Bottcher,
H. Chem. Ber. 1966, 99, 94.
8. Part of this work was presented as a poster during the 11th CRSI National
Symposium in Chemistry, NCL, Pune, India, February 6–8, 2009.
9. The new chemical entities prepared in the present work are being checked for
biological activity and the results will be published elsewhere.
10. (a) Hlasta, D. J.; Luttinger, D.; Perrone, M. H.; Silbernagel, M. J.; Ward, S. J.;
Haubrich, D. R. J. Med. Chem. 1987, 30, 1555; (b) Bermudez, J.; Dabbs, S.; Joiner,
K. A.; King, F. D. J. Med. Chem. 1990, 33, 1929; (c) Michaelis, D. J.; Dineen, T. A.
Tetrahedron Lett. 2009, 50, 1920.
Supplementary data
Supplementary data (experimental procedures and spectral
data for all compounds) associated with this article can be found,
11. (a) Tiwari, R. K.; Verma, A. K.; Chhillar, A. K.; Singh, D.; Singh, J.; Sankar, V. K.;
Yadav, V.; Sharma, G. L.; Chandra, R. Bioorg. Med. Chem. 2006, 14, 2747; (b)
Lebouvier, N.; Pagniez, F.; Duflos, M.; Le Pape, P.; Na, Y. M.; Le Baut, G.; Le
Borgne, M. Bioorg. Med. Chem. Lett. 2007, 17, 3686.
12. Procedures and spectral data for all compounds prepared in the present work
are available as supplementary data for this Letter. Spectral data for
References and notes
1. (a) Fischer, E.; Jourdan, F. Chem. Ber. 1883, 16, 2241; (b) Fischer, E.; Hess, O.
Chem. Ber. 1884, 17, 559.
2. (a) Bischler, A.; Brion, H. Ber. 1892, 25, 2860; (b) Reissert, A. Ber. 1897, 30, 1030;
(c) Noland, W. E.; Baude, F. J. Org. Synth. 1963, 43, 40; (d) Madelung, W. Ber.
1912, 45, 1128; (e) Nenitzescu, C. D. Bull. Soc. Chim. Romania 1929, 11, 37. Chem.
Abstr. 1930, 24, 110; (f) Allen, G. R., Jr.; Pidacks, C.; Weiss, M. J. J. Am. Chem. Soc.
1966, 88, 2536; (g) Hemetsberger, H.; Knittel, D. Monatsh. Chem. 1972, 103,
194; (h) Gassman, P. G.; Gruetzmacher, G.; van Bergen, T. J. J. Am. Chem. Soc.
1973, 95, 6508; (i) Batcho, A. D.; Leimgruber, W. Org. Synth. 1985, 63, 214; (j)
Bartoli, G.; Palmieri, G.; Bosco, M.; Dalpozzo, R. Tetrahedron Lett. 1989, 30,
2129; (k) Larock, R. C.; Yum, E. K.; Refvik, M. D. J. Org. Chem. 1998, 63, 7652; (l)
Tokuyama, H.; Yamashita, T.; Reding, M. T.; Kaburagi, Y.; Fukuyama, T. J. Am.
Chem. Soc. 1999, 121, 3791; (m) Robinson, B. Chem. Rev. 1963, 63, 373; (n)
Robinson, B. Chem. Rev. 1969, 69, 227; (o) Hughes, D. L. Org. Prep. Proced. Int.
1993, 25, 607; (p) Dalpozzo, R.; Bartoli, G. Curr. Org. Chem. 2005, 9, 163; (q)
Humphrey, G. R.; Kuethe, J. T. Chem. Rev. 2006, 106, 2875.
3. (a) Kaspar, L. T.; Ackermann, L. Tetrahedron 2005, 61, 11311; (b) Fang, Y.-Q.;
Lautens, M. Org. Lett. 2005, 7, 3549; (c) Du, Y.; Liu, Y.; Linn, G.; Zhao, K. Org. Lett.
2006, 8, 5919; (d) Charrier, N.; Demont, E.; Dunsdon, R.; Maile, G.; Naylor, A.;
O’Brien, A.; Redshaw, S.; Theobald, P.; Vesey, D.; Walter, D. Synthesis 2006,
3467; (e) Butin, A. V.; Smirnov, S. K.; Stroganova, T. A.; Bender, W.; Krapivin, G.
D. Tetrahedron 2007, 63, 474; (f) Miranda, S.; López-Alvarado, P.; Avendaño, C.;
Menéndez, J. C. Open Org. Chem. J. 2007, 1, 1; (g) Melkonyan, F. S.; Karchava, A.
V.; Yurovskaya, M. A. JOC 2008, 73, 4275; (h) Fang, Y.-Q.; Lautens, M. JOC 2008,
73, 538; (i) Kumar, D.; Sundaree, S.; Patel, G.; Rao, V. S. Tetrahedron Lett. 2008,
49, 867; (j) Lamar, A. A.; Nicholas, K. M. Tetrahedron 2009, 65, 3829.
representative
compounds:
2-(3-((1H-Imidazol-1-yl)methyl)-6-fluoro-3-
hydroxyindolin-1-yl)-5-pentylthiophene-3-carbonitrile (7a): IR (chloroform):
920.12, 1078.66, 1376.81, 1459.25, 1599.50, 2211.65, 2854.24, 2924.60,
3170.32, 3384.61 cmÀ1
.
1H NMR (200 MHz, CDCl3): d 0.91 (t, J = 7 Hz, 3H),
1.26–1.42 (m, 4H), 1.57–1.68 (m, 2H), 2.70 (t, J = 7 Hz, 2H), 4.05 (d, J = 12 Hz,
1H), 4.14 (d, J = 12 Hz, 1H), 4.29 (s, 2H), 4.88 (br s, 1H), 6.55 (dt, J = 2, 8 Hz, 1H),
6.67 (s, 1H), 6.75 (dd, J = 2, 10 Hz, 1H), 6.84–7.00 (m, 3H), 7.73 (s, 1H). 13C NMR
(CDCl3, 50 MHz): d 13.9, 22.2, 30.0, 30.6, 31.0, 54.7, 66.1, 98.3 (d, J = 28.18 Hz),
99.0, 108.5 (d, J = 22.68 Hz), 115.2, 121.1, 122.5, 124.9, 125.6 (d, J = 13.91 Hz),
126.6, 126.9, 135.1, 138.3, 147.3, 153.3, 164.4 (d, J = 246.27 Hz). MS (ESI), m/z:
411.5300 (M+1). 2-(3-((1H-Imidazol-1-yl)methyl)-6-fluoro-1H-indol-1-yl)-5-
pentylthiophene-3-carbonitrile (3a): IR (chloroform): 955.79, 1072.29,
1377.00, 1460.65, 1562.43, 1617.97, 2225.06, 2853.64, 2923.78,
3136.32 cmÀ1 1H NMR (200 MHz, CDCl3): d 0.93 (t, J = 7 Hz, 3H), 1.33–1.46
.
(m, 4H), 1.65–1.80 (m, 2H), 2.83 (t, J = 8 Hz, 2H), 5.43 (s, 2H), 6.91 (s, 1H), 6.99
(dt, J = 2, 8 Hz, 1H), 7.06 (s, 1H), 7.15 (s, 1H), 7.22 (dd, J = 2, 10 Hz, 1H), 7.35–
7.41 (m, 2H), 8.19 (s, 1H). 13C NMR (125 MHz, CDCl3): d 13.8, 22.2, 30.1, 30.6,
30.9, 42.7, 98.1 (d, J = 27.66 Hz), 104.5, 111.1 (d, J = 23.85 Hz), 113.5 (2C),
119.4, 120.0 (d, J = 10.49 Hz), 123.5, 126.8, 128.3, 136.5, 137.4, 137.5, 144.3,
145.8, 160.9 (d, J = 243.19 Hz). MS (ESI), m/z: 393.1017 (M+1).
13. Katritzky, A. R.; Henderson, S. A.; Yang, B. J. Heterocycl. Chem. 1998, 35,
1123.