DOI: 10.1039/C3GC41206G
Green Chemistry
= 7.5 Hz, 4H), 7.21 (t, J = 7.3 Hz, 2H), 7.14-7.06 (m, 2H), 6.80 (d,
J = 7.4 Hz, 1H), 4.28 (s, 1H), 3.71-3.67 (m, 4H), 2.52-2.48 (m, 60 Compound 4eb7
C11H11ClN2O [M+H]+: 223.0633, found: 223.0630.
4H), 2.38 (s, 3H). 13C NMR (100 MHz, CDCl3) δ 162.4, 146.9,
143.6, 142.2, 133.6, 128.7, 127.9, 127.2, 121.2, 116.7, 108.0,
76.0, 51.2, 45.8, 21.5. HRMS (ESI) calcd for C25H25N3O [M+H]+:
384.2070, found: 384.2066.
1H NMR (400 MHz, CDCl3) δ 7.12 (d, J = 8.7 Hz, 1H), 6.94 (d, J
= 2.5 Hz, 1H), 6.55 (dd, J = 8.7, 2.6 Hz, 1H), 3.80 (s, 3H), 3.67-
3.55 (m, 4H), 2.02 (m, 4H). 13C NMR (100 MHz, CDCl3) δ 161.6,
156.9, 144.4, 143.5, 108.4, 106.4, 101.2, 55.8, 47.4, 25.5. HRMS
65 (ESI) calcd for C12H14N2O2 [M+H]+: 219.1128, found: 219.1125.
N-(4-Chlorobenzoyl)piperidine 16
5
Compound 4bi9b
1H NMR (400 MHz, CDCl3) δ 7.12-7.08 (m, 5H), 7.06 (d, J = 8.1
Hz, 1H), 6.75-6.73 (m, 1H), 4.76 (s, 2H), 3.86 (t, J = 5.9 Hz, 2H),
1H NMR (400 MHz, CDCl3) δ 7.43 – 7.31 (m, 4H), 3.71 (d, J =
4.1 Hz, 2H), 3.33 (s, 2H), 1.73 – 1.57 (m, 4H), 1.53 (s, 2H). 13C
NMR (101 MHz, CDCl3) δ 168.2, 134.4, 133.8, 127.6, 127.3,
10 2.91 (t, J = 5.9 Hz, 2H), 2.31 (s, 3H). 13C NMR (100 MHz,
CDCl3) δ 161.2, 145.9, 142.2, 133.0, 132.6, 131.4, 127.7, 125.7,
125.5, 125.3, 120.2, 115.6, 107.1, 46.1, 42.0, 27.4, 20.5. HRMS 70 47.7, 42.2, 28.6, 24.5, 23.5.
(ESI) calcd for C17H16N2O [M+H]+: 265.1335, found: 265.1332.
Compound 4bj6j
15 1H NMR (400 MHz, CDCl3) δ 7.39-7.24 (m, 5H), 7.18 (s, 1H),
7.13 (d, J = 8.1 Hz, 1H), 6.82 (dd, J = 8.1, 1.0 Hz, 1H), 4.75 (s,
Acknowledgements
We thank the Chinese Academy of Sciences and the National
Natural Science Foundation of China (21133011, 21103207 and
75 21103206).
2H), 3.11 (s, 3H), 2.40 (s, 3H). 13C NMR (100 MHz, CDCl3) δ
163.2, 147.2, 143.6, 136.5, 133.6, 128.7, 127.7, 127.7, 121.0,
116.6, 108.1, 53.8, 35.2, 21.6. HRMS (ESI) calcd for C16H16N2O
20 [M+H]+: 253.1335, found: 253.1331.
Compound 4bk7
Notes and references
1H NMR (400 MHz, CDCl3) δ 7.05 (s, 1H), 6.99 (d, J = 8.1 Hz,
1H), 6.66 (dd, J = 8.1, 0.4 Hz, 1H), 4.04-3.97 (m, 1H), 2.92 (s,
3H), 2.27 (s, 3H), 1.75-1.70 (m, 4H), 1.58 (d, J = 13.1 Hz, 1H),
25 1.43-1.26 (m, 4H), 1.07-0.89 (m, 1H). 13C NMR (100 MHz,
CDCl3) δ 162.9, 146.8, 143.7, 133.3, 120.5, 116.2, 107.8, 56.6,
29.9, 29.4, 25.6, 25.4, 21.5. HRMS (ESI) calcd for C15H20N2O
[M+H]+: 245.1648, found: 245.4645.
State Key Laboratory for Oxo Synthesis and Selective Oxidation, Lanzhou
Institute of Chemical Physics, Chinese Academy of Sciences, Lanzhou,
730000, Fax: 86 931 827 7088; Tel: 86 931 496 8278; E-mail:
† Electronic Supplementary Information (ESI) available: [NMR copies of
benzolxazole derivatives and the products]. See DOI: 10.1039/b000000x/
1
(a) Oxazoles: Synthesis, Reactions and Spectroscopy, Part A, ed. D.
C. Palmer, John Wiley & Sons, Hoboken, NJ, 2003; (b) Oxazoles:
Synthesis, Reactions and Spectroscopy, Part B, ed. D. C. Palmer,
John Wiley & Sons, Hoboken, NJ, 2004; (c) Y. Ikeda, H. Nonaka, T.
Furumai, H. Onaka and Y. Igarashi, J. Nat. Prod., 2005, 68, 1061;
(d) P. Wipf, Chem. Rev., 1995, 95, 2115; (e) Z. Jin, Nat. Prod. Rep.,
2009, 26, 382.
Compound 4ab8
85
30 1H NMR (400 MHz, CDCl3) δ 7.35 (d, J = 7.3 Hz, 1H), 7.28 –
7.18 (m, 1H), 7.14 (t, J = 7.2 Hz, 1H), 7.02 – 6.91 (m, 1H), 3.58
(q, J = 7.1 Hz, 4H), 1.28 (t, J = 7.1 Hz, 6H). 13C NMR (101 MHz,
CDCl3) δ 162.2, 148.8, 143.6, 123.7, 119.9, 115.8, 108.4, 42.9,
13.4. GC-MS (EI):190.1
90 2
K. G. Liu, J. R. Lo, T. A. Comery, G. M. Zhang, J. Y. Zhang, D. M.
Kowal, D. L. Smith, L. Di, E. H. Kerns, L. E. Schechter and A. J.
Robichaud, Bioorg. Med. Chem. Lett., 2009, 19, 1115.
35 Compound 4ac6f
3
(a) A. Armstrong and J. C. Collins, Angew. Chem., Int. Ed., 2010, 49,
2282; (b) M. Zhang, Synthesis, 2011, 3408.
1H NMR (400 MHz, CDCl3) δ 7.35 (d, J = 7.7 Hz, 1H), 7.25 (d, J
= 6.4 Hz, 1H), 7.14 (t, J = 7.6 Hz, 1H), 6.98 (t, J = 7.7 Hz, 1H),
95 4
(a) J. P. Wolfe, S. Wagaw, J.-F. Marcoux, S. L. Buchwald, Acc.
Chem. Res., 1998, 31, 805; (b) J. F. Hartwig, Acc. Chem. Res., 2008,
41, 1534; (c) S. V. Ley, A. W. Thomas, Angew. Chem., Int. Ed.,
2003, 42, 5400.
4.24 (dt, J = 13.4, 6.7 Hz, 2H), 1.38 (d, J = 6.8 Hz, 12H). 13
C
NMR (101 MHz, CDCl3) δ 162.0, 148.4, 123.7, 119.8, 115.5,
40 108.4, 58.4, 20.8. GC-MS (EI): 218.1.
5
S. H. Cho, J. Y. Kim, J. Kwak and S. Chang, Chem. Soc. Rev., 2011,
40, 5068.
Compound 4ad7
100
1H NMR (400 MHz, CDCl3) δ 7.37 (dd, J = 12.1, 4.8 Hz, 1H),
7.28-7.21 (m, 1H), 7.19-7.08 (m, 1H), 7.04-6.86 (m, 1H), 3.79-
3.51 (m, 4H), 2.11-1.93 (m, 4H). 13C NMR (100 MHz, CDCl3) δ
45 160.9, 149.0, 143.6, 123.8, 120.0, 115.9, 108.5, 47.41, 25.6.
HRMS (ESI) calcd for C11H12N2O [M+H]+: 189.1022, found:
189.1025.
6
(a) D. Monguchi, T. Fujiwara, H. Furukawa and A. Mori, Org. Lett.,
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Chem. Soc., 2010, 132, 6900; (d) S. H. Cho, J. Y. Kim, S. Y. Lee
and S. Chang, Angew. Chem., Int. Ed., 2009, 48, 9127; (e) J. Y. Kim,
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9899; (f) S. Guo, B. Qian, Y. Xie, C. Xia and H. Huang, Org. Lett.,
2011, 13, 522; (g) N. Matsuda, K. Hirano, T. Satoh and M. Miura,
Org. Lett., 2011, 13, 2860; (h) J. Wang, J.-T. Hou, J. Wen, J. Zhang
and X.-Q. Yu, Chem. Commun., 2011, 47, 3652. (i) Y. Li, Y. Xie, R.
Zhang, K. Jin, X. Wang and C. Duan, J. Org. Chem., 2011, 76, 5444;
(j) Y. Li, J. Liu, Y. Xie, R. Zhang, K. Jin, X. Wang and C. Duan,
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50, 11511.
(a) T. Froehr, C. P. Sindlinger, U. Kloeckner, P. Finkbeiner and B. J.
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105
110
Compound 4cb7
1H NMR (400 MHz, CDCl3) δ 7.23 (d, J = 7.9 Hz, 1H), 7.07 (s,
50 1H), 6.95 (d, J = 7.7 Hz, 1H), 3.63 (s, 4H), 2.39 (s, 3H), 2.02 (s,
4H). 13C NMR (100 MHz, CDCl3) δ 160.8, 149.2, 141.1, 129.9,
124.4, 115.3, 109.1, 47.3, 25.6, 21.4. HRMS (ESI) calcd for
C12H14N2O [M+H]+: 203.1179, found: 203.1175.
7
115 8
Compound 4db7
55 1H NMR (400 MHz, CDCl3) δ 7.31 (d, J = 1.9 Hz, 1H), 7.14 (d, J
= 8.4 Hz, 1H), 6.96-6.91 (m, 1H), 3.67-3.63 (m, 4H), 2.06-1.97
(m, 4H). 13C NMR (100 MHz, CDCl3) δ 161.6, 147.6, 144.9,
129.1, 119.8, 116.0, 109.0, 47.4, 25.5. HRMS (ESI) calcd for
9
120 10 S. Liu, R. Chen, X. Guo, H. Yang, G. Deng and C. Li, Green Chem.,
2012, 14, 1577.
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