2
926
J. Jadhav et al. / Tetrahedron 69 (2013) 2920e2926
4. Kallashi, F.; Kim, D.; Kowalchick, J.; Park, Y. J.; Hunt, J. A.; Ali, A.; Smith, C. J.;
2
360, 1643, 1575, 1531, 1482, 1445, 1337, 1242, 1189, 1156, 1117,
ꢀ
1
1
Hammond, M. L.; Pivnichny, J. V.; Tong, X.; Xu, S. S.; Anderson, M. S.; Chen, Y.;
Eveland, S. S.; Guo, Q.; Hyland, S. A.; Milot, D. P.; Cumiskey, A. M.; Latham, M.;
Peterson, L. B.; Rosa, R.; Sparrow, C. P.; Wright, S. D.; Sinclair, P. J. Bioorg. Med.
Chem. Lett. 2011, 21, 558.
1
071 cm
AreH), 7.72e7.69 (1H, m, AreH), 7.58 (2H, d, J¼7.4 Hz, AreH),
.53e7.49 (1H, m, AreH), 7.43e7.35 (3H, m, AreH), 7.33e7.29 (2H, m,
;
H NMR (300 MHz, CDCl
3
):
d
7.78 (1H, d, J¼7.9 Hz,
7
13
5. Grobler, J. A.; Dornadula, G.; Rice, M. R.; Simcoe, A. L.; Hazuda, D. J.; Miller, M. D.
J. Biol. Chem. 2007, 282, 8005.
AreH), 7.07 (1H, d, J¼15.9 Hz, Olefine); C NMR (75 MHz, CDCl
3
):
d
162.8, 150.4, 142.1, 139.4, 135.1, 129.8, 129.0, 127.5, 125.2, 124.5,
19.8, 113.9, 110.3; MS (EI): m/z 221 (M ).
6. Nishiu, J.; Ito, M.; Ishida, Y.; Kakutani, M.; Shibata, T.; Matsushita, M.; Shindo, M.
þ
1
Diabetes, Obes. Metab. 2006, 8, 508.
7. (a) Yu, Z.; Ma, L.; Yu, W. Synlett 2012, 1534; (b) Kalkhambkar, R. G.; Laali, K. K.
Tetrahedron Lett. 2012, 53, 4212; (c) Wen, X.; Bakali, J. E.; Deprez-Poulain, R.;
Deprez, B. Tetrahedron Lett. 2012, 53, 2440; (d) Kawashita, Y.; Nakamichi, N.;
Kawabata, H.; Hayashi, M. Org. Lett. 2003, 5, 3713; (e) Pottorf, R. S.; Chadha, N.
K.; Katkevics, M.; Ozola, V.; Suna, E.; Ghane, H.; Regberg, T.; Player, M. R. Tet-
rahedron Lett. 2003, 44, 175; (f) Chang, J.; Zhao, K.; Pan, S. Tetrahedron Lett. 2002,
4
.5.5. 2-(4-Methoxyphenyl)-benzoxazole (Table 2, entry h). Pale yel-
ꢁ
ꢁ
8c
low solid (57.0 mg, 90%); mp 97e98 C (lit., 98 C); [found: C, 74.65;
H, 4.92; N, 6.22. C14 requires C, 74.69; H, 4.96; N, 6.29%]; R
10% hexane/EtOAc) 0.51; IR (KBr, thin film):
¼3045, 2978, 2841,
644,1616,1603,1580,1503,1452,1420,1344,1319,1303,1254,1242,
H11NO
2
f
(
1
n
43, 951.
8. (a) Altenhoff, G.; Glorius, F. Adv. Synth. Catal. 2004, 346, 1661; (b) Barbero, N.;
Carril, M.; SanMartin, R.; Domínguez, E. Tetrahedron 2007, 63, 10425; (c)
Evindar, G.; Batey, R. A. J. Org. Chem. 2006, 71, 1802; (d) Viirre, R. D.; Evindar, G.;
Batey, R. A. J. Org. Chem. 2008, 73, 3452; (e) Ueda, S.; Nagasawa, H. J. Org. Chem.
2009, 74, 4272; (f) Saha, P.; Tamminana, R.; Purkait, N.; Ali, M. A.; Paul, R.;
Punniyamurthy, T. J. Org. Chem. 2009, 74, 8719.
ꢀ
1 1
1187, 1059, 1019 cm ; H NMR (300 MHz, CDCl ): d 8.17 (2H, d,
3
J¼9.1 Hz, AreH), 7.73e7.70 (1H, m, AreH), 7.54e7.51 (1H, m, AreH),
7
OCH
.31e7.28 (2H, m, AreH), 7.00 (2H, d, J¼9.1 Hz, AreH), 3.85 (3H, s,
13
3
); C NMR (75 MHz, CDCl
3
):
d
163.1, 150.6, 142.2, 129.3, 124.5,
þ
9. Peng, J.; Zong, C.; Ye, M.; Chen, T.; Gao, D.; Wang, Y.; Chen, C. Org. Biomol. Chem.
124.4, 119.6, 119.5, 114.3, 110.3, 55.4 (OCH
3
); MS (EI): m/z 225 (M ).
2011, 9, 1225.
10. (a) Holbrey, J. D.; Seddon, K. R. J. Chem. Soc., Dalton Trans. 1999, 2133; (b)
4
.5.6. 2-(Furan-2-yl)-benzoxazole (Table 2, entry k). Pale brown solid
Welton, T. Chem. Rev. 1999, 99, 2071; (c) Earle, M. J.; McCormac, P. B.; Seddon, K.
R. Green Chem. 1999, 1, 23; (d) Reetz, M. T.; Wiesenh o€ fer, W.; Franci oꢀ , G.; Leitner,
W. Chem. Commun. 2002, 992; (e) Gu, Y.; Ogawa, C.; Kobayashi, S. Org. Lett.
ꢁ
ꢁ
20b
(
42.0 mg, 70%); mp 83e84 C (lit., 89e90 C);
.81; N, 7.56. C11 NO requires C, 71.30; H, 3.79; N, 7.50%]; R
hexane/EtOAc) 0.3; IR (KBr, thin film):
¼3060, 2919, 2849, 1681,
626,1592,1524,1484,1457,1309,1249,1156,1087,1060,1005 cm
[found: C, 71.35; H,
3
H
7
2
f
(10%
2007, 9, 175; (f) Olivier, B. H.; Magna, L. J. Mol. Catal. A: Chem. 2002, 419, 182.
n
11. Wassercheid, P. Angew. Chem., Int. Ed. 2000, 39, 3772.
12. Riisager, A.; Jørgensen, B.; Wasserscheid, P.; Fehrmann, R. Chem. Commun.
ꢀ
1
1
;
2006, 994.
1
H NMR (300 MHz, CDCl
3
): d 7.71e7.74 (1H, m, AreH), 7.63e7.64 (1H,
1
3. Riisager, A.; Fehrmann, R.; Haumann, M.; Wasserscheid, P. Top. Catal. 2006,
t, J¼1.7 Hz, AreH), 7.29e7.34 (2H, m, AreH), 7.51e7.54 (1H, m,
40, 91.
13
14. (a) Hagiwara, H.; Sugawara, Y.; Isobe, K.; Hoshi, T.; Suzuki, T. Org. Lett. 2004,
AreH), 7.25 (1H, s, AreH), 6.59e6.57 (1H, dd, J¼1.7, Hz, AreH);
C
6
, 2325; (b) Huang, J.; Jiang, T.; Gao, H.; Han, B.; Liu, Z.; Wu, W.; Chang, Y.;
NMR (75 MHz, CDCl
3
):
d
155.2, 150.0, 145.7, 142.4, 141.5, 125.2, 124.8,
Zhao, G. Angew. Chem. 2004, 43, 1397; (c) Mehnert, C. P.; Cook, R. A.;
Dispenziere, N. C.; Afeworki, M. J. Am. Chem. Soc. 2002, 124, 12932; (d)
Haumann, M.; Dentler, K.; Joni, J.; Riisager, A.; Wasserscheid, P. Adv. Synth.
Catal. 2007, 349, 425; (e) Chen, W.; Zhang, Y.; Zhu, L.; Lan, J.; Xie, R.; You, J. J.
Am. Chem. Soc. 2007, 129, 13879; (f) Joni, J.; Haumann, M.; Wasserscheid, P.
Adv. Synth. Catal. 2009, 351, 423; (g) Kotadia, D. A.; Joshi, S. S. J. Mol. Catal. A:
Chem. 2012, 101, 353; (h) Shylesh, S.; Hanna, D.; Werner, S.; Bell, A. T. ACS
Catal. 2012, 2, 487; (i) Villar-Garcia, I. J.; Abebe, A.; Chebude, Y. Inorg. Chem.
Commun. 2012, 19, 1.
þ
120.0, 114.2, 112.2, 110.5; MS (EI): m/z 185 (M ).
Acknowledgements
The authors GSR and RSS thank UGC, New Delhi for financial
assistance [F. No. 40-96/2011 (SR)].
1
5. (a) Kumbhar, A.; Kamble, S.; Barge, M.; Rashinkar, G.; Salunkhe, R. Tetrahedron
Lett. 2012, 53, 2756; (b) Kamble, S.; Kumbhar, A.; Rashinkar, G.; Barge, M.;
Salunkhe, R. Ultrason. Sonochem. 2012, 19, 812; (c) Jadhav, J.; Gaikwad, V.;
Kurane, R.; Salunkhe, R.; Rashinkar, G. Synlett 2012, 2511.
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