8.1 Hz); 13C NMR (75 MHz, TMS, DMSO-d6): δ 159.1, 155.1,
144.2, 131.9, 127.3, 125.3, 121.9, 113.9, 61.3, 50.5, 46.0, 43.4,
28.0, 15.0; ESI-HRMS: m/z calcd for C16H22N3O3 [M + H]:
304.1656, found: 304.1661.
M. Costa, J. Org. Chem., 2004, 69, 4741; (c) M. Kamrin, W. F. Bertsch
and R. F. Wood, Proc. Natl. Acad. Sci. U. S. A., 1965, 53, 1118.
2 (a) A. Teimouri, N. Soltani and A. N. Chermahini, Front. Chem. Sci.
Eng., 2011, 5, 43; (b) R. Amjad, M. A. Munawar, S. R. Khan, M. Naeem
and M. Sohaib, J. Chem. Soc. Pak., 2011, 33, 107 and references cited
therein; (c) X.-Y. Cao, J.-C. Zheng, Y.-X. Li, Z.-C. Shu, X.-L. Sun,
B.-Q. Wang and Y. Tang, Tetrahedron, 2010, 66, 9703; (d) Z. Zhang and
P. R. Schreiner, Chem. Soc. Rev., 2009, 38, 1187.
3 (a) A. C. Nicholas and K. L. Yielding, Mol. Chem. Neuropathol., 1998,
35, 1; (b) N. Tewari, V. K. Tiwari, R. C. Mishra, R. P. Tripathi,
A. K. Srivastava, R. Ahmad, R. Srivastava and B. S. Srivastava, Bioorg.
Med. Chem., 2003, 11, 2911; (c) P. Boden, J. M. Eden, J. Hodgson,
D. C. Horwell, W. Howson, J. Hughes, A. T. McKnight, K. Meecham,
M. C. Pritchard, J. Raphy, G. S. Ratcliffe, N. Suman-Chauhan and
G. N. Woodruff, Bioorg. Med. Chem. Lett., 1994, 4, 1679.
4 P. Boden, J. M. Eden, J. Hodgson, D. C. Horwell, M. C. Pritchard,
J. Raphy and N. Suman-Chauhan, Bioorg. Med. Chem. Lett., 1995, 5,
1773.
5 (a) Q. Han, C.-H. Chang, R. Li, Y. Ru, P. K. Jadhav and P. Y. S. Lam,
J. Med. Chem., 1998, 41, 2019 and references cited therein;
(b) J.-F. Guichou, J. Viaud, C. Mettling, G. Subra, Y.-L. Lin and
A. Chavanieu, J. Med. Chem., 2006, 49, 900.
Methyl 4-(indoline-1-carbonyl)piperazine-1-carboxylate (27c).
Prepared by general procedure 5. Yield 81%; Rf = 0.4 (hexane–
EtOAc, 3 : 2). Light brown solid, mp 105 °C; IR (KBr): 3386,
3009, 2895, 2855, 2732, 2677, 2492, 2409, 2206, 2057, 1950,
1914, 1877, 1713, 1642, 1599, 1409, 1283, 1247, 1124, 988,
1
762 cm−1; H NMR (300 MHz, TMS, CDCl3): δ 7.21–7.13 (m,
2H), 7.06–7.03 (m, 1H), 6.95–6.90 (m, 1H), 3.95 (t, 2H, J = 8.1
Hz), 3.74 (s, 3H), 3.58–3.55 (m, 4H), 3.40–3.36 (m, 4H), 3.05
(t, 2H, J = 8.1 Hz); 13C NMR (75 MHz, TMS, CDCl3): δ 159.2,
155.8, 143.5, 131.7, 127.1, 125.1, 121.9, 112.9, 52.8, 50.4, 46.3,
43.6, 27.8; ESI-HRMS: m/z calcd for C15H19N3NaO3 [M + Na]:
312.1319, found: 312.1316.
6 (a) P. Y. Lam, P. K. Jadhav, C. J. Eyermann, C. N. Hodge, Y. Ru,
L. T. Bacheler, J. L. Meek, M. J. Otto, M. M. Rayner, Y. N. Wong,
C. H. Chang, P. C. Weber, D. A. Jackson, T. R. Sharpe and S. Erickson-
Viitanen, Science, 1994, 263, 380; (b) L.-E. Trudeau, P. Fossier, G. Baux
and L. Tauc, Brain Res., 1992, 586, 78.
7 (a) S. Mand, K. Pfarr, P. K. Sahoo, A. K. Satapathy, S. Specht,
U. Klarmann, A. Y. Debrah, B. Ravindran and A. Hoerauf, Am. J. Trop.
Med. Hyg., 2009, 81, 702; (b) G. Guercio, S. Bacchi, A. Perboni,
C. Leroi, F. Tinazzi, I. Bientinesi, M. Hourdin, M. Goodyear, S. Curti,
S. Provera and Z. Cimarosti, Org. Process Res. Dev., 2009, 13, 1100;
(c) Y. Zhu, S. Xia, M. Zhu, W. Yi, J. Cheng, G. Song, Z. Li and P. Lu,
Eur. J. Med. Chem., 2010, 45, 4953.
8 For review see: (a) T. P. Vishnyakova, I. A. Golubeva and E. V. Glebova,
Russ. Chem. Rev., 1985, 54, 249; (b) A. A. Bakibaev, A. Y. Yagovkin and
S. N. Vostretsov, Russ. Chem. Rev., 1998, 67, 295; (c) F. Biggi, R. Maggi
and G. Sartori, Green Chem., 2000, 2, 140.
9 (a) A. R. Katritzky, N. Kirichenko and B. V. Rogovoy, ARKIVOC, 2003,
8 and references cited therein (b) C. Han and J. A. Porco Jr., Org. Lett.,
2007, 9, 1517 and references cited therein (c) X.-Q. Li, W.-K. Wang,
Y.-X. Han and C. Zhang, Adv. Synth. Catal., 2010, 352, 2588;
(d) G. Verardo, E. Bombardella, C. D. Venneri and P. Strazzolini,
Eur. J. Org. Chem., 2009, 6239; (e) P. Liu, Z. Wang and X. Hu,
Eur. J. Org. Chem., 2012, 1994.
[4-(Indoline-1-carbonyl)piperazin-1-yl]-indolin-1-yl-methanone
(28c). Prepared by general procedure 5; Rf = 0.5 (hexane–
EtOAc, 1 : 4); Light brown solid, mp 252 °C; IR (KBr): 3118,
3043, 3014, 2928, 2899, 2854, 2668, 1941, 1899, 1856, 1707,
1642, 1600, 1483, 1396, 1272, 1237, 1160, 992 cm−1; 1H NMR
(300 MHz, TMS, CDCl3): δ 7.05–7.24 (m, 6H), 6.88–6.99 (m,
2H), 3.95 (t, 4H, J = 8.3 Hz), 3.47 (s, 8H), 3.04 (t, 4H, J = 8.3
Hz); 13C NMR (75 MHz, TMS, CDCl3): δ 159.3, 143.4, 131.7,
127.1, 125.1, 121.9, 112.9, 50.3, 46.3, 27.8; ESI-HRMS: m/z
calcd for C22H25N4O2 [M + H]: 377.1972, found: 377.1968.
[1-(Imidazole-1-carbonyl)-4-piperidyl]-indolin-1-yl-metha-
none (30c). Prepared by general procedure 5. Yield 78%; Rf =
0.3 (EtOAc). Light brown solid, mp 203 °C; IR (KBr): 3350,
3295, 3140, 3115, 3019, 2962, 2878, 2582, 2109, 1901, 1868,
1678, 1598, 1460, 1421, 1324, 1276, 1231, 1181, 1036,
1
995 cm−1; H NMR (300 MHz, TMS, CDCl3): δ 8.22 (d, 1H),
7.88 (s, 1H), 7.01–7.33 (m, 5H), 4.23–4.08 (m, 4H), 3.26–3.14
(m, 4H), 2.86–2.77 (m, 1H), 2.03–1.91 (m, 4H); 13C NMR
(75 MHz, TMS, CDCl3): δ 170.8, 149.9, 141.8, 135.9, 130.1,
128.8, 126.7, 123.6, 123.1, 116.9, 116.3, 46.9, 44.8, 39.8, 27.0,
26.9; ESI-HRMS: m/z calcd for C18H21N4O2[M + H]: 325.1659,
found: 325.1657.
10 P. Majer and R. S. Randad, J. Org. Chem., 1994, 59, 1937.
11 (a) S.-H. Lee, H. Matsushita, B. Clapham and K. D. Janda, Tetrahedron,
2004, 60, 3439; (b) S.-H. Lee, H. Matsushita, G. Koch, J. Zimmermann,
B. Clapham and K. D. Janda, J. Comb. Chem., 2004, 6, 822;
(c) E. Bridgeman and N. C. O. Tomkinson, Synlett, 2006, 243.
12 A. R. Katritzky, D. P. M. Pleynet and B. Yang, J. Org. Chem., 1997, 62,
4155.
13 (a) J. H. Park, J. C. Yoon and Y. K. Chung, Adv. Synth. Catal., 2009,
351, 1233; (b) E. García-Egido, M. Fernández-Suárez and L. Muñoz,
J. Org. Chem., 2008, 73, 2909; (c) J. E. McCusker, A. D. Main,
K. S. Johnson, C. A. Grasso and L. McElwee-White, J. Org. Chem.,
2000, 65, 5216 and references cited therein.
[1-(Indoline-1-carbonyl)-4-piperidyl]-indolin-1-yl-methanone
(31c). Prepared by general procedure 5. Yield 10%; Rf = 0.35
(hexane–EtOAc, 1 : 4). Light brown solid, mp 210–212 °C; IR
(KBr): 3294, 3141, 2962, 1934, 1901, 1677, 1654, 1598, 1485,
14 J. E. McCusker, C. A. Grasso, A. D. Main and L. McElwee-White, Org.
Lett., 1999, 1, 961.
1421, 1230, 1182, 748 cm−1 1H NMR (300 MHz, TMS,
;
CDCl3): δ 8.5 (m, 1H), 7.25–7.00 (m, 6H), 6.93–6.86 (m, 1H),
4.2 (t, 2H, J = 8.1 Hz), 3.96–3.90 (m, 4H), 3.26–3.23 (m, 2H),
3.1–2.9 (m, 4H), 2.72–2.64 (m, 1H), 2.10–1.78 (m, 4H);
13C NMR (75 MHz, TMS, CDCl3): δ 172.8, 159.6, 143.9,
143.0, 131.6, 131.1, 127.6, 127.1, 124.9, 124.6, 123.9, 121.6,
117.4, 112.9, 50.4, 47.9, 46.0, 41.7, 29.7, 28.1, 27.9;
ESI-HRMS: m/z calcd for C23H26N3O2 [M + H]: 376.2020,
found: 376.2011.
15 (a) T. Mizuno, T. Nakai and M. Mihara, Synthesis, 2010, 4251;
(b) T. Yoshida, N. Kambe, S. Murai and N. Sonoda, Tetrahedron Lett.,
1986, 27, 3037; (c) T. Mizuno, T. Nakai and M. Mihara, Heteroat.
Chem., 2009, 20, 64.
16 N. S. Nudelman, E. S. Lewkowicz and D. G. Perez, Synthesis, 1990, 917.
17 D. Chaturvedi, N. Mishra and V. Mishra, Monatsh. Chem., 2008, 139,
267.
18 (a) J. A. Fritz, J. S. Nakhla and J. P. Wolfe, Org. Lett., 2006, 8, 2531;
(b) T. Hafner and D. Kunz, Synthesis, 2007, 1403; (c) B. J. Kotecki,
D. P. Fernando, A. R. Haight and K. A. Lukin, Org. Lett., 2009, 11, 947.
19 (a) D. Liptrot, L. Alcaraz and B. Roberts, Adv. Synth. Catal., 2010, 352,
2183; (b) C.-C. Lee, P.-S. Wang, M. B. Viswanath and M.-K. Leung,
Synthesis, 2008, 9, 1359.
20 (a) J. Lefranc, D. J. Tetlow, M. Donnard, A. Minassi, E. Galvez and
J. Clayden, Org. Lett., 2011, 13, 296; (b) S. Breitler, N. J. Oldenhuis,
B. P. Fors and S. L. Buchwald, Org. Lett., 2011, 13, 3262.
Notes and references
1 (a) S. Batra, Z. Tusi and S. Madapa, Curr. Med. Chem.: Anti-Infective
Agents, 2006, 5, 135; (b) B. Gabriele, G. Salerno, R. Mancuso and
6430 | Org. Biomol. Chem., 2012, 10, 6420–6431
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