Beilstein J. Org. Chem. 2013, 9, 818–826.
15.Yu, S.; Ma, S. Angew. Chem., Int. Ed. 2012, 51, 3074.
45.LaLonde, R. L.; Wang, Z. J.; Mba, M.; Lackner, A. D.; Toste, F. D.
46.Li, H.; Widenhoefer, R. A. Org. Lett. 2009, 11, 2671.
16.Rivera-Fuentes, P.; Diederich, F. Angew. Chem., Int. Ed. 2012, 51,
17.Krause, N.; Winter, C. Chem. Rev. 2011, 111, 1994.
47.Winter, C.; Krause, N. Angew. Chem., Int. Ed. 2009, 48, 6339.
18.Alcaide, B.; Almendros, P. Chem. Rec. 2011, 11, 311.
48.Yeom, H.-S.; Lee, E.-S.; Shin, S. Synlett 2007, 2292.
19.Alcaide, B.; Almendros, P.; Aragoncillo, C. Chem. Soc. Rev. 2010, 39,
49.Singh, S.; Elsegood, M. R. J.; Kimber, M. C. Synlett 2012, 565.
20.Brasholz, M.; Reissig, H.-U.; Zimmer, R. Acc. Chem. Res. 2009, 42,
50.Alcaide, B.; Almendros, P.; Quirós, M. T.; López, R.; Menéndez, M. I.;
Sochacka-Ćwikła, A. J. Am. Chem. Soc. 2013, 135, 898.
21.Krause, N., Ed. Compounds with all carbon functions: Cumulenes and
Allenes; Science of Synthesis; Georg Thieme: Stuttgart, Germany,
2007; Vol. 44.
51.Alcaide, B.; Almendros, P.; Cembellín, S.; Martínez del Campo, T.;
Fernández, I. Chem. Commun. 2013, 49, 1282.
23.Krause, N.; Hashmi, A. S. K., Eds. Modern Allene Chemistry;
Wiley-VCH: Weinheim, Germany, 2004.
52.Alcaide, B.; Almendros, P.; Alonso, J. M.; Fernández, I.
53.Alcaide, B.; Almendros, P.; Aragoncillo, C.; Gómez-Campillos, G.;
Arnó, M.; Domingo, L. R. ChemPlusChem 2012, 77, 563.
24.Alcaide, B.; Almendros, P. Eur. J. Org. Chem. 2004, 3377.
25.Bates, R. W.; Satcharoen, V. Chem. Soc. Rev. 2002, 31, 12.
54.Alcaide, B.; Almendros, P.; Alonso, J. M.; Quirós, M. T.; Gadziński, P.
55.Alcaide, B.; Almendros, P.; Carrascosa, R. Chem.–Eur. J. 2011, 17,
26.Zimmer, R.; Dinesh, C. U.; Nandanan, E.; Khan, F. A. Chem. Rev.
27.Hashmi, A. S. K. Angew. Chem., Int. Ed. 2000, 39, 3590.
56.Bélanger, D.; Tong, X.; Soumaré, S.; Dory, Y. L.; Zhao, Y.
57.Spangenberg, T.; Schoenfelder, A.; Breit, B.; Mann, A.
58.Paul, A.; Bittermann, H.; Gmeiner, P. Tetrahedron 2006, 62, 8919.
28.Hashmi, A. S. K.; Toste, F. D., Eds. Modern Gold Catalyzed Synthesis;
Wiley-VCH: Weinheim, Germany, 2012.
29.Rudolph, M.; Hashmi, A. S. K. Chem. Soc. Rev. 2012, 41, 2448.
30.Corma, A.; Leyva-Pérez, A.; Sabater, M. J. Chem. Rev. 2011, 111,
We used the Dess–Martin oxidation and the Ohira–Bestmann reagent
instead of the reported Swern oxidation and Corey–Fuchs olefination.
59.Crabbé, P.; Fillion, H.; André, D.; Luche, J.-L.
J. Chem. Soc., Chem. Commun. 1979, 859.
31.Rudolph, M.; Hashmi, A. S. K. Chem. Commun. 2011, 47, 6536.
32.Alcaide, B.; Almendros, P.; Alonso, J. M. Org. Biomol. Chem. 2011, 9,
60.Kuang, J.; Ma, S. J. Org. Chem. 2009, 74, 1763.
34.Hashmi, A. S. K. Angew. Chem., Int. Ed. 2010, 49, 5232.
61.Decker, M. Curr. Med. Chem. 2011, 18, 1464.
35.Lipshutz, B.; Yamamoto, Y., Eds. Coinage Metals in Organic
Synthesis. Chem. Rev. 2008, 108, 2793–3442.
36.Hutchings, G. J.; Brust, M.; Schmidbaur, H., Eds. Gold – Chemistry,
Materials and Catalysis. Chem. Soc. Rev. 2008, 37, 1745–2140.
39.Jiménez-Núñez, E.; Echavarren, A. M. Chem. Commun. 2007, 333.
Compounds 3d–f and 4d–f can be considered as hybrid scaffolds, i.e.,
as a combination of the biologically relevant β-lactam and oxazinone
frameworks. See for a review on hybrid chemical entities.
62.Tsogoeva, S. B. Mini-Rev. Med. Chem. 2010, 10, 773.
64.Tietze, L. F.; Bell, H. P.; Chandrasekhar, S. Angew. Chem., Int. Ed.
40.Hashmi, A. S. K.; Hutchings, G. J. Angew. Chem., Int. Ed. 2006, 45,
65.Kochanowska-Karamyan, A. J.; Hamann, M. T. Chem. Rev. 2010, 110,
41.Zhang, L.; Sun, J.; Kozmin, S. A. Adv. Synth. Catal. 2006, 348, 2271.
Fused tricyclic 3,4-dihydro-2H-1,3-oxazin-2-one 4j was more efficiently
obtained by performing the reaction at 80 °C. Fused indole derivatives
are represented in numerous natural alkaloids and synthetic
pharmaceuticals, which display a number of interesting biological
activities.
See for a review.
42.Alcaide, B.; Almendros, P. Adv. Synth. Catal. 2011, 353, 2561.
43.Higginbotham, M. C. M.; Bebbington, M. W. P. Chem. Commun. 2012,
66.Bandini, M.; Eichholzer, A. Angew. Chem., Int. Ed. 2009, 48, 9608.
44.Hashmi, A. S. K.; Schuster, A. M.; Litters, S.; Rominger, F.;
Pernpointner, M. Chem.–Eur. J. 2011, 17, 5661.
67.Humphrey, G. R.; Kuethe, J. T. Chem. Rev. 2006, 106, 2875.
825