Beilstein J. Org. Chem. 2011, 7, 1468–1474.
15.Bandini, M. Chem. Soc. Rev. 2011, 40, 1358–1367.
1,5-Dimethyl-8-phenyl-5,6-dihydropyrrolo[3,2-
c]azepin-4(1H)-one (13a)
16.England, D. B.; Padwa, A. Org. Lett. 2008, 10, 3631–3634.
Yield: 63% (Table 4, entry 1). White solid; mp 130 °C; IR
(nujol) ν: 1676 cm−1; 1H NMR (599 MHz, CDCl3) δ 3.07 (s,
3H), 3.17 (s, 3H), 3.74 (d, J = 7.2 Hz, 2H), 6.13 (t, J = 7.2 Hz,
1H), 6.63 (d, J = 2.8 Hz, 1H), 6.77 (d, J = 2.8 Hz, 1H), 7.22 (d,
J = 6.4 Hz, 2H), 7.32–7.35 (m, 3H); 13C NMR (150 MHz,
CDCl3) δ 35.3 (q), 36.4 (q), 47.5 (t), 109.6 (d), 123.2 (s), 124.3
(d), 124.7 (d), 127.5 (d), 128.0 (d), 128.6 (d), 131.5 (s), 137.8
(s), 139.3 (s), 166.0 (s); MS m/z: 253 [M]+; Anal. calcd for
C16H16N2O: C, 76.16; H, 6.39; N, 11.10; found: C, 76.23; H,
6.30; N, 11.04.
17.Verniest, G.; England, D.; De Kimpe, N.; Padwa, A. Tetrahedron 2010,
18.Gruit, M. M.; Michalik, D.; Krüger, K.; Spannenberg, A.; Tillack, A.;
Pews-Davtyan, A.; Beller, M. Tetrahedron 2010, 66, 3341–3352.
19.Ferrer, C.; Echavarren, A. M. Angew. Chem., Int. Ed. 2006, 45,
20.Broggini, G.; Molteni, G.; Terraneo, A.; Zecchi, G. Heterocycles 2003,
21.Beccalli, E. M.; Broggini, G.; Martinelli, M.; Paladino, G.; Zoni, C.
22.Abbiati, G.; Beccalli, E. M.; Broggini, G.; Paladino, G.; Rossi, E.
23.Abbiati, G.; Beccalli, E. M.; Broggini, G.; Martinelli, M.; Paladino, G.
Supporting Information
Supporting Information File 1
24.Beccalli, E. M.; Broggini, G.; Martinelli, M.; Masciocchi, N.;
25.Beccalli, E. M.; Borsini, E.; Broggini, G.; Rigamonti, M.;
Sottocornola, S. Synlett 2008, 1053–1057.
Experimental procedures and characterization data.
26.Beccalli, E. M.; Broggini, G.; Clerici, F.; Galli, S.; Kammerer, C.;
Rigamonti, M.; Sottocornola, S. Org. Lett. 2009, 11, 1563–1566.
Acknowledgements
The authors thank the Ministero dell’Università e della Ricerca
for financial support (PRIN 2008KRBX3B) and Stefano
Provera for helpful discussions.
27.Basolo, L.; Beccalli, E. M.; Borsini, E.; Broggini, G. Tetrahedron 2009,
28.Beccalli, E. M.; Borsini, E.; Brenna, S.; Galli, S.; Rigamonti, M.;
Broggini, G. Chem.–Eur. J. 2010, 16, 1670–1678.
References
29.Beccalli, E. M.; Bernasconi, A.; Borsini, E.; Broggini, G.; Rigamonti, M.;
30.Broggini, G.; Beccalli, E. M.; Borsini, E.; Fasana, A.; Zecchi, G. Synlett
1. Nakamura, I.; Yamamoto, Y. Chem. Rev. 2004, 104, 2127–2198.
2. Li, J. J.; Gribble, G. W. Palladium in Heterocyclic Chemistry. A Guide
for the Synthetic Chemist; Pergamon: New York, 2000.
3. Godoi, B.; Schumacher, R. F.; Zeni, G. Chem. Rev. 2011, 111,
31.Borsini, E.; Broggini, G.; Colombo, F.; Khansaa, M.; Fasana, A.;
Galli, S.; Passarella, D.; Riva, E.; Riva, S. Tetrahedron: Asymmetry
32.Borsini, E.; Broggini, G.; Fasana, A.; Galli, S.; Khansaa, M.; Piarulli, U.;
Rigamonti, M. Adv. Synth. Catal. 2011, 353, 985–994.
4. Beccalli, E. M.; Broggini, G.; Fasana, A.; Rigamonti, M.
J. Organomet. Chem. 2011, 696, 277–295.
5. Patil, N. T.; Yamamoto, Y. Chem. Rev. 2011, 111, 3395–3442.
33.Beccalli, E. M.; Broggini, G.; Martinelli, M.; Paladino, G. Tetrahedron
34.Manzo, A. M.; Perboni, A. D.; Broggini, G.; Rigamonti, M.
Tetrahedron Lett. 2009, 50, 4696–4699.
6. Shen, H. C. Tetrahedron 2008, 64, 3885–3903.
7. Shen, H. C. Tetrahedron 2008, 64, 7847–7870.
35.Manzo, A. M.; Perboni, A. D.; Broggini, G.; Rigamonti, M. Synthesis
8. Jiménez-Núñez, E.; Echavarren, A. M. Chem. Rev. 2008, 108,
36.Chezal, J.-M.; Paeshuyse, J.; Gaumet, V.; Canitron, D.; Maisonial, A.;
Lartigue, C.; Gueiffier, A.; Moreau, E.; Teulade, J.-C.; Chavignon, O.;
Neyts, J. Eur. J. Med. Chem. 2010, 45, 2044–2047.
10.Marion, N.; Nolan, S. P. Chem. Soc. Rev. 2008, 37, 1776–1782.
11.Fürstner, A. Chem. Soc. Rev. 2009, 38, 3208–3221.
37.Sahoo, S. P.; Chen, M.-H.; Dykstra, K. D.; Koyama, H.; Meinke, P. T.;
O'Keefe, S. J.; Yang, G. X.-Q. Pyrrolo [2,3-c] pyridine derivatives as
P38 kinase inhibiting agents. PCT Patent WO2009/152072 A1, Dec 17,
2009.
12.Shapiro, N. D.; Toste, F. D. Synlett 2010, 675–691.
13.Corma, A.; Leyva-Pérez, A.; Sabater, M. J. Chem. Rev. 2011, 111,
14.Krause, N.; Winter, C. Chem. Rev. 2011, 111, 1994–2009.
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