JOURNAL OF CHEMICAL RESEARCH 2018 89
132.1, 131.0, 129.0, 126.1, 124.8, 123.2, 121.4, 121.3, 120.1, 111.9; MS
m/z (%): 228 (M+). Anal. calcd for C14H9ClO: C, 73.53; H, 3.97; found:
C, 73.70; H, 4.07%.
13C NMR (100 MHz, CDCl3): δ 142.1, 140.2, 132.3, 132.2, 131.9, 129.4,
129.3, 129.2, 124.2, 115.9; MS m/z (%): 465 (M+). Anal. calcd for
C22H12Br2O2: C, 56.44; H, 2.58; found: C, 56.61; H, 2.53%.
1-Phenylnaphtho[2,1-b]furan25 (Table 2, entry 7): Yellow oil;
3,8-Diphenylnaphtho[2,1-b:6,5-b′]difuran (Table 2, entry 13):
yield 0.224 g (92%,); IR (KBr) (υ cm−1): 3039, 1661, 1602, 1479,
Brown oil; yield 0.266 g (74%); IR (KBr) (υ cm−1): 3011, 1669, 1489,
1
1
1405; H NMR (400 MHz, CDCl3): δ 8.05 (d, J = 8.3 Hz, 1H), 7.99
1464; H NMR (400 MHz, CDCl3): δ 7.80 (d, J = 8.1 Hz, 1H), 7.74
(d, J = 8.0 Hz, 1H), 7.82 (d, J = 9.0 Hz, 1H), 7.75 (d, J = 9.0 Hz, 1H),
7.73 (s, 1H), 7.66 (dd, J = 8.0, 1.4 Hz, 2H), 7.59–7.52 (m, 3H), 7.49 (td,
J = 7.8, 1.2 Hz, 1H), 7.41 (td, J = 8.0, 1.2 Hz, 1H); 13C NMR (100 MHz,
CDCl3): δ 153.2, 141.7, 133.1, 130.9, 129.9, 128.9, 128.6, 128.4, 127.9,
126.0, 125.9, 124.5, 124.4, 123.4, 120.8, 112.7; MS m/z (%): 244 (M+).
Anal. calcd for C18H12O: C, 88.50; H, 4.95; found: C, 88.69; H, 5.02%.
1-(4-Bromophenyl)naphtho[2,1-b]furan25 (Table 2, entry 8): Yellow
oil; yield 0.260 g (81%); IR (KBr) (υ cm−1): 3050, 1657, 1604, 1481,
1451; 1H NMR (400 MHz, CDCl3): δ 7.72 (s, 1H), 7.70 (d, J = 7.1 Hz,
2H), 7.53 (d, J = 8.5 Hz, 2H), 7.48 (d, J = 7.9 Hz, 1H), 7.44 (d,
J = 8.5 Hz, 2H), 7.31–7.22 (m, 3H); 13C NMR (100 MHz, CDCl3): δ
153.2, 141.7, 132.4, 131.8, 131.5, 131.0, 130.0, 129.4, 129.0, 127.9, 126.2,
126.1, 125.0, 124.5, 123.2, 112.7; MS m/z (%): 322 (M+). Anal. calcd
for C18H11BrO: C, 66.89; H, 3.43; found: C, 66.71; H, 3.38%.
(d, J = 8.1 Hz, 1H), 7.64–7.57 (m, 3H), 7.47–7.41 (m, 2H), 7.39–7.35
(m, 1H), 7.24–7.21 (m, 3H), 7.17–7.10 (m, 2H), 7.08–7.04 (m, 2H),
6.96–6.95 (m, 1H); 13C NMR (100 MHz, CDCl3): δ 155.8, 141.4, 132.1,
131.0, 129.0, 126.1, 124.8, 123.2, 121.3, 120.1, 111.9; MS m/z (%): 360
(M+). Anal. calcd for C26H16O2: C, 86.65; H, 4.47; found: C, 86.48; H,
4.35%.
3,8-Bis(4-bromophenyl)naphtho[2,1-b:6,5-b′]difuran (Table 2,
entry 14): Brown oil; yield 0.391 g (76%); IR (KBr) (υ cm−1): 3009,
1669, 1491, 1466; 1H NMR (400 MHz, CDCl3): δ 8.14 (d, J = 8.0 Hz,
1H), 7.88 (d, J = 7.9 Hz, 1H), 7.72–7.60 (m, 7H), 7.44–7.41 (m, 2H),
7.38–7.34 (m, 1H), 7.33–7.30 (m, 2H); 13C NMR (100 MHz, CDCl3): δ
155.9, 141.1, 132.0, 131.7, 125.1, 124.6, 123.9, 123.2, 122.4, 117.4, 109.9;
MS m/z (%): 515 (M+). Anal. calcd for C26H14Br2O2: C, 60.26; H, 2.72;
found: C, 60.48; H, 2.67%.
3,5-Diphenylbenzo[1,2-b:5,4-b′]difuran26 (Table 2, entry 11):
Yellow oil; yield 0.202 g (65%); IR (KBr) (υ cm−1): 3014, 1659,
1
Received 29 November 2017; accepted 26 December 2017
Paper 1705127
Published online: 16 February 2018
1601, 1481, 1405; H NMR (400 MHz, CDCl3): δ 8.09 (s, 2H), 7.86
(s, 1H), 7.77 (s, 1H), 7.59 (d, J = 8.4 Hz, 4H), 7.50 (m, 4H), 7.39 (m,
2H); 13C NMR (100 MHz, CDCl3): δ 155.1, 151.7, 130.3, 129.1, 128.9,
127.9, 127.4, 125.1, 121.9, 118.5; MS m/z (%): 310 (M+). Anal. calcd for
C22H14O2: C, 85.14; H, 4.55; found: C, 85.31; H, 4.48 %.
References
Analytical and spectroscopic data for the unknown compounds
1
A. Hiremathad, M.R. Patil, K.R. Chethana, K. Chand, M.A. Santos and
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3-(4-Bromophenyl)-5-fluorobenzofuran (Table 2, entry 5): Yellow oil;
yield 0.246 g (85%); IR (KBr) (υ cm−1): 3041, 1676, 1648, 1579, 1476,
1461; 1H NMR (400 MHz, CDCl3): δ 7.97 (d, J = 8.6 Hz, 2H), 7.73 (s,
1H), 7.59 (d, J = 8.6 Hz, 2H), 7.35–7.29 (m, 1H), 6.96–6.90 (m, 2H);
13C NMR (100 MHz, CDCl3): δ 155.3, 150.2, 142.5, 132.0, 131.7, 130.3,
129.1, 128.1, 117.5, 113.2, 110.0, 109.7; MS m/z (%): 289 (M+). Anal.
calcd for C14H8BrFO: C, 57.76; H, 2.77; found: C, 57.58; H, 2.82%.
3-(4-Bromophenyl)-5-chlorobenzofuran (Table 2, entry 6): Yellow
oil; yield 0.256 g (84%); IR (KBr) (υ cm−1): 3051, 1635, 1605, 1489,
1451; 1H NMR (400 MHz, CDCl3): δ 7.97 (d, J = 8.6 Hz, 2H), 7.72 (s,
1H), 7.66 (s, 1H), 7.59 (d, J = 8.6 Hz, 2H), 7.33 (d, J = 8.8 Hz, 1H), 7.08
(d, J = 8.8 Hz, 1H); 13C NMR (100 MHz, CDCl3): δ 152.1, 142.0, 140.3,
132.1, 131.7, 129.7, 126.8, 125.5, 123.5, 123.1, 121.7, 112.0; MS m/z (%):
305 (M+). Anal. calcd for C14H8BrClO: C, 54.67; H, 2.62; found: C,
54.80; H, 2.70%.
2
3
4
H. Khanam, Eur. J. Med. Chem., 2015, 97, 483.
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R. Salmon, J. Buisson, B. Zafrani, L. Aussepe and R. Royer, Carcinogenesis,
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8
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M.M. Heravi and V. Zadsirjan, Adv. Heterocycl. Chem., 2015, 117, 261.
M.M. Heravi, V. Zadsirjan, H. Hamidi and P.H.T. Amiri, RSC Adv., 2017,
7, 24470.
10 P. Tharra, and B. Baire, Chem. Commun., 2016, 52, 14290.
11 V.P.R. Lingam, D.H. Dahale, K. Mukkanti, B. Gopalan and A. Thomas,
Tetrahedron Lett., 2012, 53, 5695.
1-(Biphenyl-4-yl)naphtho[2,1-b]furan (Table 2, entry 9): Yellow
oil; yield 0.285 g (89%); IR (KBr) (υ cm−1): 3026, 1669, 1486, 1460;
1H NMR (400 MHz, CDCl3): δ 8.01 (d, J = 8.4 Hz, 1H), 7.88 (d,
J = 7.6 Hz, 1H), 7.72 (s, 1H), 7.70–7.60 (m, 9H), 7.44–7.29 (m, 5H);
13C NMR (100 MHz, CDCl3): δ 153.2, 141.8, 132.0, 130.9, 130.8, 130.4,
130.2, 129.0, 128.9, 127.7, 127.5, 127.3, 127.1, 126.0, 125.3, 124.4,
124.1, 123.4, 112.7; MS m/z (%): 320 (M+). Anal. calcd for C24H16O: C,
89.97; H, 5.03; found: C, 89.78; H, 4.95%.
12 J.H. Lee, M. Kim, and I. Kim, J. Org. Chem., 2014, 79, 6153.
13 M.J. Moure, R. SanMartin and E. Dominguez, Angew. Chem. Int. Ed.,
2012, 51, 3220.
14 N. Sakiyama, K. Noguchi and K. Tanaka, Angew. Chem. Int. Ed., 2012,
51, 5976.
15 C. Huo, J. An, X. Xu, X. Jia, X. Wang and L. Kang, Tetrahedron Lett.,
2013, 54, 1145.
16 K. Sonogashira, Y. Tohda and N. Hagihara, Tetrahedron Lett., 1975, 16,
4467.
1-(Naphthalen-2-yl)naphtho[2,1-b]furan (Table 2, entry 10): Yellow
oil; yield 0.253 g (86%); IR (KBr) (υ cm−1): 3002, 1659, 1605, 1392;
1H NMR (400 MHz, CDCl3): δ 7.98 (s, 1H), 7.91 (d, J = 8.3 Hz, 2H),
7.88–7.85 (m, 2H), 7.83–7.81 (m, 1H) 7.72–7.63 (m, 4H), 7.49–7.46
(m, 2H) 7.36–7.32 (m, 1H), 7.24–7.20 (m, 1H); 13C NMR (100 MHz,
CDCl3): δ 153.3, 141.9, 133.5, 132.9, 129.6, 130.8, 130.6, 128.9, 128.5,
128.2, 128.1, 127.9, 126.5, 126.3, 126.1, 126.0, 124.4, 123.2, 112.7; MS
m/z (%): 294 (M+). Anal. calcd for C22H14O: C, 89.77; H, 4.79; found:
C, 89.59; H, 4.84%.
3,5-Bis(4-bromophenyl)benzo[1,2-b:5,4-b′]difuran (Table 2, entry
12): Yellow oil; yield 0.312 g (67%); IR (KBr) (υ cm−1): 3018, 1667,
1607, 1491, 1452; 1H NMR (400 MHz, CDCl3): δ 9.70 (s, 2H), 7.78 (d,
J = 8.4 Hz, 4H); 7.66 (d, J = 8.4 Hz, 4H), 7.57 (s, 1H), 7.37 (s, 1H);
17 R. Jindal and A.S. Surya, Curr. Green Chem., 2015, 2, 135.
18 R.L. Vekariya, J. Mol. Liq., 2017, 227, 44.
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24 G. Liu and X. Lu. Tetrahedron, 2008, 64, 7324.
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26 Z. Chen, X. Wang, W. Lu and J. Yu. Synlett, 1991, 1991, 121.