Zhong-Zhen Zhou et al.
COMMUNICATIONS
another portion of 3a (yield: 85 mg, 0.36 mmol). Thus, com-
pound 3a was obtained in 97% yield (230 mg, 0.97 mmol)
under microwave irradiation.
Compounds 3b–l were synthesized in a similar way. All
the compounds were fully characterized by MS and NMR
(1H and 13C) (see Supporting Information). Shown below
are the structural data of new compounds 3f–l.
(75 MHz, DMSO-d6): d=22.0 (Me), 123.8 (C-12), 125.9 (C-
11), 126.1 (C-13 and C-8), 129.6 (C-2 and C-6), 129.9 (C-3
and C-5), 134.3 (C-10), 134.5 (C-14), 137.2 (C-4), 144.0 (C-
1), 145.2 (C-9), 148.8 (C-15), 182.3 (C=O).
2-(4-Chlorobenzoyl)-7-nitrobenzofuran-3-ol (3l): ESI MS:
m/z=340.09
[M+Na]+,
318.32
[M+1]+;
1H NMR
(300 MHz, DMSO-d6): d=7.51 (t, J=7.8 Hz, 1H, H-12),
7.62 (d, J=8.7 Hz, 2H, H-2 and H-6), 8.05 (d, J=8.4 Hz,
2H, H-3 and H-5), 8.33 (d, J=7.8 Hz, 1H, H-13), 8.38 (d,
J=7.8 Hz, 1H, H-11); 13C NMR (75 MHz, DMSO-d6): d=
123.8 (C-12), 126.4 (C-11 and C-8), 129.1 (C-2 and C-6),
130.0 (C-13), 131.6 (C-3 and C-5), 134.3 (C-10), 136.3 (C-1),
137.1 (C-14), 138.1 (C-4), 145.6 (C-9), 149.4 (C-15), 181.2
(C=O).
2-(4-Methoxybenzoyl)-5-methoxybenzofuran-3-ol
(3f):
Negative ESI-MS: m/z=297.07 [MÀH]À; 1H NMR
(300 MHz, CDCl3): d=3.89 (s, 3H, OMe), 3.90 (s, 3H,
OMe), 6.87–6.90 (s and dd, overlapped, 2H, H-11 and H-
13), 6.99–7.04 (m, 2H, H-2 and H-6), 7.65 (d, J=8.7 Hz, 1H,
H-14), 8.30–8.35 (m, 2H, H-3 and H-5); 13C NMR
(100 MHz, CDCl3): d=55.47 (MeO), 55.7 (MeO), 95.7 (C-
11), 113.3 (C-8), 113.4 (C-114), 113.8 (C-2 and C-6), 122.3
(C-13), 127.3 (C-10), 131.5 (C-3 and C-5), 135.4 (C-4), 158.0
(C-15), 162.3 (C-9), 163.2 (C-12), 163.4 (C-1), 176.3 (C=O).
2-(4-Methylbenzoyl)-5-methoxybenzofuran-3-ol (3g): Neg-
ative ESI-MS: m/z=281.09 [MÀH]À;1H NMR (300 MHz,
CDCl3): d=2.45 (s, 3H, Me), 3.99 (s, 3H, OMe), 6.86–6.90
(s and dd, overlapped, 2H, H-11, H-13), 7.31 (d, J=8.1 Hz,
2H, H-3 and H-5), 7.66 (dd, J=8.1 Hz and 0.9 Hz, 1H, H-
14), 8.19 (d, J=8.1 Hz, 2H, H-2 and H-6); 13C NMR
(100 MHz, CDCl3): d=21.7 (Me), 55.7 (OMe), 95.7 (C-11),
113.4 (C-14), 113.5 (C-13), 122.5 (C-8), 129.2 (C-2 and C-6),
129.3 (C-3 and C-5), 131.8 (C-10), 135.6 (C-4), 143.5 (C-1),
158.6 (C-15), 163.7 (C-12 and C-9), 176.9 (C=O).
Acknowledgements
This work was financially supported by Natural Science
Foundation of Guangdong Province (9451051501002541),
Medical Scientific Research Foundation of Guangdong Prov-
ince (B2008103) (ZZZ), Southern Medical University and
Department of Education of Guangdong Province, China
(WHC).
2-(4-Chlorobenzoyl)-5-methoxybenzofuran-3-ol (3h): Neg-
ative ESI-MS: m/z=301.07 [MÀH]À; 1H NMR (300 MHz,
CDCl3): d=3.89 (s, OMe), 6.87–6.91 (m, 2H, H-11 and H-
12), 7.46~7.51 (m, 2H, H-3 and H-5), 7.66 (d, J=9.2 Hz,
1H, H-14), 8.22–8.26 (m, 2H, H-2 and H-6); 13C NMR
(100 MHz, CDCl3): d=55.8 (OMe), 95.7 (C-11), 113.2 (C-
14), 113.8 (C-13), 122.7 (C-8), 128.8 (C-2 and C-6), 130.6 (C-
3 and C-5), 132.8 (C-10), 135.5 (C-1), 138.9 (C-4), 158.9 (C-
15), 164.1 (C-9), 164.5 (C-12), 174.1 (C=O).
2-Benzoyl-7-nitrobenzofuran-3-ol (3i): ESI-MS: m/z=
306.04 [M+Na]+, 284.06 [M+1]+; 1H NMR (300 MHz,
DMSO-d6): d=7.53~7.60 (t and t, overlapped, 3H, H-2, H-
6 and H-12), 7.67 (t, J=7.2 Hz, 1H, H-1), 8.08 (d, J=
6.9 Hz, 2H, H-3 and H-5), 8.33 (d, J=7.8 Hz, 1H, H-13),
8.38 (d, J=7.8 Hz, 1H, H-11); 13C NMR (75 MHz, DMSO-
d6): d=123.9 (C-12), 126.0 (C-11), 126.3 (C-13 and C-8),
129.0 (C-2 and C-6), 129.8 (C-3 and C-5), 133.4 (C-10), 134.4
(C-1), 137.2 (C-14), 137.4 (C-4), 145.4 (C-9), 148.8 (C-15),
182.8 (C=O).
2-(4-Methoxybenzoyl)-7-nitrobenzofuran-3-ol (3j): ESI
MS: m/z=336.11 [M+Na]+, 314.22 [M+1]+; 1H NMR
(300 MHz, DMSO-d6): d=3.83 (s, 3H, OMe), 7.10 (d, J=
8.4 Hz, 2H, H-2 and H-6), 7.52~7.59 (m, 1H, H-12), 8.18 (d,
J=8.4 Hz, 2H, H-3 and H-5), 8.29 (d, J=7.5 Hz, 1H, H-13),
8.37 (d, J=7.8 Hz, 1H, H-11); 13C NMR (75 MHz, DMSO-
d6): d=56.3 (OMe), 114.4 (C-2 and C-6), 123.8 (C-12), 125.8
(C-11), 126.1 (C-8), 129.4 (C-13), 129.5 (C-10), 132.3 (C-3
and C-5), 134.3 (C-14), 137.2 (C-4), 145.1 (C-9), 148.8 (C-
15), 163.7 (C-1), 181.2 (C=O).
2-(4-Methylbenzoyl)-7-nitrobenzofuran-3-ol (3k): ESI
MS: m/z=320.13 [M+Na]+, 298.10 [M+1]+; 1H NMR
(300 MHz, DMSO-d6): d=2.43 (s, 3H, Me), 7.37 (d, J=
8.1 Hz, 2H, H-2 and H-6), 7.55 (t, J=8.1 Hz, 1H, H-12),
8.02 (d, J=7.8 Hz, 2H, H-3 and H-5), 8.31 (d, J=7.8 Hz,
1H, H-13), 8.38 (d, J=8.1 Hz, 1H, H-11); 13C NMR
References
[1] a) A. Stroba, F. Schaeffer, V. Hindie, L. L. Garcia, I.
Adrian, W. Frohner, R. W. Hartmann, R. M. Biondi, M.
Engel, J. Med. Chem. 2009, 52, 4683–4693; b) K. Tsuchi-
kama, Y. K. Hashimoto, K. Endo, T. Shibata, Adv.
Synth. Catal. 2009, 351, 2850–2854; c) S. Mahboobi, A.
Sellmer, H. Hçcher, C. Garhammer, H. Pongratz, T.
Maier, T. Ciossek, T. Beckers, J. Med. Chem. 2007, 50,
4405–4418; d) W. Huang, M. Z. Liu, Y. Li, Y. Tan, G. F.
Yang, Bioorg. Med. Chem. 2007, 15, 5191–5197; e) B.
Gabriele, R. Mancuso, G. Salerno, M. Costac, Adv.
Synth. Catal. 2006, 348, 1101–1109; f) E. Bellur, P.
Langer, J. Org. Chem. 2005, 70, 7686–7693; g) K. Ando,
E. Tsuji, Y. Ando, N. Kuwata, J. Kunitomo, M. Yamashi-
ta, S. Ohta, S. Kohno, Y. Ohishi, Org. Biomol. Chem.
2004, 2, 625–635.
[2] a) E. Martin, B. Felix, S. Alessandro, R. Subho, S.
Goutam, S. K. Kumar, S. Rohit, S. Sudhir, Patent WO
2005061476A2, 2005; Chem. Abstr. 2005, 143, 115430;
b) M. Gerard, L. Caroline, K. Micheline, Patent FR
2862646A1, 2005; Chem. Abstr. 2005, 143, 7588; c) H. A.
Pershadsingh, D. E. Levy, Patent WO 2000000194A1,
2000; Chem. Abstr. 2000, 132, 73666.
[3] a) W. A. Mosher, A. D. Serridgaen, D. D. Lipp, J. Org.
Chem. 1972, 37, 2402–2405; b) F. Gatta, G. Settimj, J.
Heterocycl. Chem. 1984, 21, 937–943; c) M. G. Joshi,
K. N. Wadodkar, Indian J. Chem. Sect. B 1981, 20, 930–
931; d) D. Kevin, R. Paul, S. Robert, T. Allyson, W.
David, A. Lee, US Patent 6,297,238 B1, 2001; Chem.
Abstr. 2001, 135, 272953.
[4] a) T. A. Geissman, A. Armen, J. Am. Chem. Soc. 1955,
77, 1623–1627; b) B. Bryant, D. L. Haslam, J. Chem.
Soc. 1965, 2361–2364; c) B. Bryant, J. Chem. Soc. 1965,
5140–5141.
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Adv. Synth. Catal. 2010, 352, 1909 – 1913