3J = 8.6 Hz, 1 H), 7.41 (d, 3J = 1.7 Hz, 1 H), 7.48 (d, 3J = 8.2 Hz,
2 H), 9.01 (s, 1 H). 13C NMR (125 MHz, CDCl3): d 14.3 (CH3),
21.3 (CH3), 100.1 (Cquat), 109.3 (CH), 112.3 (CH), 112.5 (CH),
119.5 (CH), 123.8 (CH), 126.2 (CH), 127.0 (Cquat), 128.8 (Cquat),
129.3 (CH), 129.5 (Cquat), 129.8 (Cquat), 133.8 (Cquat), 137.5 (Cquat),
137.6 (Cquat), 138.0 (Cquat), 142.4 (CH), 145.4 (Cquat), 161.5 (Cquat).
Notes and references
1 B. S. Joshi, W. I. Taylor, D. S. Bhate and S. S. Karmarkar, Tetrahedron,
1963, 19, 1437.
2 G. R. Pettit, J. C. Knight, D. L. Herald, R. Davenport, R. K. Pettit, B.
E. Tucker and J. M. Schmidt, J. Nat. Prod., 2002, 65, 1793.
3 S. Takahashi, T. Matsunaga, C. Hasegawa, H. Saito, D. Fujita, F.
Kiuchi and Y. Tsuda, Chem. Pharm. Bull., 1998, 46, 1527.
4 F. Miyake, M. Hashimoto, S. Tonsiengsom, K. Yakushijin and D. A.
Horne, Tetrahedron, 2010, 66, 4888; G. Guella, I. Mancini, I. N’Diaye
and F. Pietra, Helv. Chim. Acta, 1994, 77, 1999.
5 R. Ferna´ndez, M. J. Mart´ın, R. Rodr´ıguez-Acebes, F. Reyes, A.
Francesch and C. Cuevas, Tetrahedron Lett., 2008, 49, 2283; N.
Lindquist, W. Fenical, G. D. Van Duyne and J. Clardy, J. Am. Chem.
Soc., 1991, 113, 2303.
6 Z. Cruz-Monserrate, H. C. Vervoort, R. Bai, D. J. Newman, S. B.
Howell, G. Los, J. T. Mullaney, M. D. Williams, G. R. Pettit, W. Fenical
and E. Hamel, Mol. Pharmacol., 2003, 63, 1273.
7 A. Nishida, M. Fuwa, Y. Fujikawa, E. Nakahata, A. Furuno and M.
Nakagawa, Tetrahedron Lett., 1998, 39, 5983.
MS (MALDI-TOF): m/z = 387.9, 389.0. UV/Vis (EtOH): lmax
-1
˜
(e) [nm] = 253 (4000), 321 (9400). IR (KBr): n [cm ] = 3423 (m),
3173 (m), 1719 (w), 1655 (w), 1626 (w), 1587 (m), 1561 (w), 1543
(w), 1494 (m), 1469 (m), 1433 (w), 1404 (w), 1375 (w), 1314 (w),
1291 (m), 1273 (w), 1235 (w), 1194 (w), 1164 (w), 1094 (s), 1074
(w), 1062 (m), 1011 (m), 971 (w), 945 (m), 933 (m), 885 (w), 849
(w), 832 (m), 789 (s), 756 (w), 743 (w), 716 (w), 701 (w), 687 (m),
590 (w), 508 (w). Anal. calcd. for C23H17ClN2O2 + 0.33 CH2Cl2
(388.9 + 28.0): C 67.18, H 4.27, N 6.72; Found.: C 67.58, H 4.67,
N 6.75%.
8 S. R. Naik, J. Harindran and A. B. Varde, J. Biotechnol., 2001, 88, 1.
9 D. Kumar, S. Sundaree, G. Patel and A. Kumar, J. Heterocycl. Chem.,
2010, 47, 1425; D. Kumar, S. Sundaree, G. Patel and V. S. Rao,
Tetrahedron Lett., 2008, 49, 867.
5-(5-Chloro-2-(3-chlorophenyl)-1H-indol-3-yl)-4-(4-chlorophenyl)-
2-methyloxazole (4x)
10 J. D. Sunderhaus and S. F. Martin, Chem.–Eur. J., 2009, 15, 1300; N.
Isambert and R. Lavilla, Chem.–Eur. J., 2008, 14, 8444; A. Do¨mling,
Chem. Rev., 2006, 106, 17; R. V. A. Orru and M. de Greef, Synthesis,
2003, 1471; B. B. Toure´ and D. G. Hall, Chem. Rev., 2009, 109, 4439; H.
Bienayme´, C. Hulme, G. Oddon and P. Schmitt, Chem.–Eur. J., 2000,
6, 3321; A. Do¨mling and I. Ugi, Angew. Chem., Int. Ed., 2000, 39,
3168; I. Ugi, A. Do¨mling and B. Werner, J. Heterocycl. Chem., 2000,
37, 647; L. Weber, K. Illgen and M. Almstetter, Synlett, 1999, 366; R.
W. Armstrong, A. P. Combs, P. A. Tempest, S. D. Brown and T. A.
Keating, Acc. Chem. Res., 1996, 29, 123; I. Ugi, A. Do¨mling and W.
Ho¨rl, Endeavour, 1994, 18, 115; G. H. Posner, Chem. Rev., 1986, 86,
831.
Yellow solid, Mp. 225 ◦C. 1H NMR (500 MHz, CDCl3): d 2.56 (s,
3 H), 7.10 (d, 3J = 8.4 Hz, 2 H), 7.18–7.25 (m, 4 H, 7.36–7.40 (m,
5 H), 8.77 (s, 1 H). 13C NMR (125 MHz, CDCl3): d 14.3 (CH3),
102.3 (Cquat), 112.5 (CH), 116.4 (Cquat), 119.8 (CH), 124.3 (CH),
125.5 (CH), 127.2 (Cquat), 127.3 (CH), 127.7 (CH), 128.6 (CH),
128.9 (CH), 129.2 (Cquat), 130.3 (CH), 133.0 (Cquat), 133.3 (Cquat),
134.4 (Cquat), 135.0 (Cquat), 136.1 (Cquat), 137.0 (Cquat), 139.6 (Cquat),
161.6 (Cquat). MS (MALDI-TOF): m/z = 452.9, 454.9. UV/Vis
-1
11 L. F. Tietze, Chem. Rev., 1996, 96, 115.
˜
(EtOH): lmax (e) [nm] = 306 (43900). IR (KBr): n [cm ] = 3416
12 D. M. D’Souza and T. J. J. Mu¨ller, Chem. Soc. Rev., 2007, 36, 1095; G.
Balme, E. Bossharth and N. Monteiro, Eur. J. Org. Chem., 2003, 4101;
K. Khanbabaee, Nachr. Chem., 2003, 51, 691; G. Battistuzzi, S. Cacchi
and G. Fabrizi, Eur. J. Org. Chem., 2002, 2671.
(s), 2923 (m), 1655 (w), 1583 (m), 1512 (w), 1492 (m), 1466 (m),
1446 (m), 1382 (w), 1364 (w), 1334 (w), 1281 (m), 1220 (m), 1184
(w), 1159 (w), 1105 (w), 1064 (m), 1007 (s), 950 (m), 884 (w), 861
(w), 823 (m), 798 (m), 734 (s), 561 (w), 509 (w). Anal. calcd. for
C24H15Cl3N2O (453.8): C 63.53, H 3.33, N 6.17; Found: C 63.28,
H 3.32, N 6.17%.
13 T. J. J. Mu¨ller, Top. Heterocycl. Chem., 2010, 25, 25; B. Willy and T. J. J.
Mu¨ller, Curr. Org. Chem., 2009, 13, 1777; B. Willy and T. J. J. Mu¨ller,
ARKIVOC, 2008, Part I, 195; T. J. J. Mu¨ller, Targets in Heterocyclic
Systems, 2006, 10, 54.
14 T. J. J. Mu¨ller and D. M. D’Souza, Pure Appl. Chem., 2008, 80, 609; T. J.
J. Mu¨ller, In “Functional Organic Materials. Syntheses, Strategies, and
Applications”, T. J. J. Mu¨ller, U. H. F. Bunz, eds, Wiley-VCH Verlag
GmbH & Co. KGaA, Weinheim, 2007, 179.
5-(5-Chloro-2-(3-chlorophenyl)-1H-indol-3-yl)-2-methyl-4-p-
tolyloxazole (4y)
15 For recent reviews, see e.g. K. Kru¨ger, A. Tillack and M. Beller, Adv.
Synth. Catal., 2008, 350, 2153; G. R. Humphrey and J. T. Kuethe, Chem.
Rev., 2006, 106, 2875; S. Cacchi and G. Fabrizi, Chem. Rev., 2005, 105,
2873; G. Zeni and R. C. Larock, Chem. Rev., 2004, 104, 2285.
16 For reviews, see e.g. B. Robinson, Chem. Rev., 1969, 69, 227; D.
L. Hughes, Org. Prep. Proced. Int., 1993, 25, 607. For a review on
mechanistic aspects, see e.g.; N. M. Przheval’skii, L. Y. Kostromina
and I. I. Grandberg, Chem. Heterocycl. Compd., 1989, 24, 709. For a
modern variation in the sense of a multiple condensation reaction, see
e.g.; C. A. Simoneau and B. Ganem, Tetrahedron, 2005, 61, 11374.
17 J. M. Zhang, P. Y. Coqueron and M. A. Ciufolini, Heterocycles, 2011,
82, 949.
18 P. Wipf and C. P. Miller, J. Org. Chem., 1993, 58, 3604; P. Wipf and S.
Lim, J. Am. Chem. Soc., 1995, 117, 558; A. J. Phillips, Y. Uto, P. Wipf,
M. J. Reno and D. R. Williams, Org. Lett., 2000, 2, 1165; P. Wipf and
J.-L. Methot, Org. Lett., 2001, 3, 1261.
19 P. Wipf, L. T. Rahman and S. R. Rector, J. Org. Chem., 1998, 63, 7132;
A. Arcadi, S. Cacchi, L. Cascia, G. Fabrizi and F. Marinelli, Org. Lett.,
2001, 3, 2501; P.-Y. Coqueron, C. Didier and M. A. Ciufolini, Angew.
Chem., Int. Ed., 2003, 42, 1411.
Yellow solid, Mp. 187 ◦C. 1H NMR (500 MHz, CDCl3): d 2.25 (s,
3 H), 2.54 (s, 3 H), 6.95 (d, 3J = 8.2 Hz, 2 H), 7.16 (d, 3J = 7.7 Hz, 1
H), 7.21–7.24 (m, 3 H), 7.35–7.39 (m, 5 H), 8.71 (s, 1H). 13C NMR
(125 MHz, CDCl3): d 14.3 (CH3), 21.3 (CH3), 102.8 (Cquat), 112.4
(CH), 116.4 (Cquat), 119.9 (CH), 124.1 (CH), 125.6 (CH), 126.4
(CH), 127.1 (Cquat), 127.3 (CH), 128.7 (CH), 128.9 (Cquat), 129.1
(CH), 129.5 (Cquat), 130.2 (CH), 133.2 (Cquat), 134.4 (Cquat), 134.9
(Cquat), 136.9 (Cquat), 137.4 (Cquat), 138.6 (Cquat), 161.3 (Cquat). MS
(MALDI-TOF): m/z = 432.9. UV/Vis (EtOH): lmax (e) [nm] = 314
-1
˜
(9600). IR (KBr): n [cm ] = 3398 (s), 1638 (m), 1465 (w), 1062(w),
786 (m), 685 (m). Anal. calcd. for C25H18Cl2N2O (433.3): C 69.29,
H 4.19, N 6.46; Found: C 69.02, H 4.18, N 6.46%.
Acknowledgements
20 A. S. K. Hashmi, J. P. Weyrauch, W. Frey and J. W. Bats, Org. Lett.,
2004, 6, 4391.
21 E. Merkul, O. Grotkopp and T. J. J. Mu¨ller, Synthesis, 2009, 502; E.
Merkul and T. J. J. Mu¨ller, Chem. Commun., 2006, 4817.
22 For reviews on microwave-assisted syntheses of heterocycles, see e.g. H.
M. Hu¨gel, Molecules, 2009, 14, 4936; M. C. Bagley and M. C. Lubinu,
The financial support of this work by the Evonik (stipend for
O. G.) and by the Fonds der Chemischen Industrie is gratefully
acknowledged. The authors also thank the BASF SE for the
generous donation of chemicals.
This journal is
The Royal Society of Chemistry 2011
Org. Biomol. Chem., 2011, 9, 8130–8140 | 8139
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