DOI: 10.1039/C7OB00845G
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Organic & Biomolecular Chemistry
1
For selected reviews, see: (a) V. P. Boyarskiy, D. S.
Ryabukhin, N. A. Bokach, and A. V. Vasilyev, Chem.
Rev., 2016, 116, 5894; (b) Z. Zheng, Z. Wang, Y. Wang,
and L. Zhang, Chem. Soc. Rev., 2016, 45, 4448; (c) H.
Yoshida, ACS Catal., 2016, 6, 1799; (d) M. Pirnot, Y.-M.
Wang, and S. Buchwald, Angew. Chem., Int. Ed., 2016, 55,
48; (e) M. Heravi, M. Tamimi, H. Yahyavi and T.
Hosseinnejad, Curr. Org. Chem., 2016, 20, 1591; (e) L.
Ackermann, Acc. Chem. Res., 2014, 47, 281; (f) R.
Chinchila, and C. Najera, Chem. Rev., 2014, 114, 1783; (g)
A. Fuerstner, Angew. Chem., Int. Ed., 2013, 52, 2794.
For selected examples, see: (a) G. Qiu and J. Wu Chem.
Record. 2016, 16, 19; (b) L. He, H. Nie, G. Qiu, Y. Gao
and J. Wu, Org. Biomol. Chem. 2014, 12, 9045; (c) H.
Wang, Y. Kuang, and J. Wu, Asian J. Org. Chem. 2012, 1,
302.
4-Bromo-3-butyl-1H-isochromen-1-one (4e)4d (39.4 mg, 70%)
60
65
70
75
80
85
90
95
00
05
10
15
20
1H NMR (400 MHz, CDCl3) δ 8.27 (d, J = 7.8 Hz, 1H), 7.91 –
7.71 (m, 2H), 7.64 – 7.39 (m, 1H), 2.82 (t, J = 7.7 Hz, 2H), 1.80 –
5 1.68 (m, 2H), 1.50 – 1.38 (m, 2H), 0.96 (t, J = 7.3 Hz, 3H). 13
NMR (100 MHz, CDCl3) δ 161.55, 155.76, 136.33, 135.33,
129.71, 128.44, 125.67, 120.22, 101.14, 33.19, 28.95, 22.23,
13.78.
C
10 4-Bromo-7-methyl-3-phenyl-1H-isochromen-1-one (4f) (52.3 mg,
83%)
2
1H NMR (400 MHz, CDCl3) δ 8.15 (s, 1H), 7.75 (d, J = 8.2 Hz,
1H), 7.83 – 7.73 (m, 2H), 7.68 – 7.62 (m, 1H), 7.50 – 7.41 (m,
3H), 2.52 (s, 3H). 13C NMR (100 MHz, CDCl3) δ 161.39, 150.90,
15 139.72, 136.66, 134.21, 132.80, 130.04, 129.65, 129.55, 128.06,
126.63, 120.37, 101.42, 21.23. HRMS (ESI) calcd for
3
4
M. A. Oliver and R. D. Gandour, J. Org. Chem. 1984, 49,
558.
Iodocyclization of o-alkynylbenzoates: (a) T. Yao and R.
C. Larock, J. Org. Chem. 2003, 68, 5936; (b) T. Yao and
R. C. Larock, Tetrahedron Lett. 2002, 43, 7401; (c) S.
Mehta, J. P. Waldo, and R. C. Larock, J. Org. Chem. 2009,
74, 1141; (d) M. Peuchmaur, V. Lisowski, C. Gandreuil, L.
T. Maillard, J. Martinez and J.-F. Hernandez, J. Org.
Chem. 2009, 74, 4158; (e) A. K. Verma, V. Rustagi, T.
Aggarwal, A. P. Singh, J. Org. Chem. 2010, 75, 7691; (f)
A. K. Verma, T. Aggarwal, V. Rustagi, and R. C. Larock,
Chem. Commun. 2010, 46, 4064; (g) J. Barluenga, L.
Llavona, M. Yus, and J. M. Concellon, Tetrahedron Lett.
1991, 47, 7875.
+
C16H12BrO2 : 315.0015 (M++H), found: 315.0018
4,7-Dibromo-3-phenyl-1H-isochromen-1-one (4g) (57.0 mg, 75%)
20 1H NMR (400 MHz, CDCl3) δ 8.48 (d, J = 2.0 Hz, 1H), 7.94 (dd,
J = 8.6, 2.2 Hz, 1H), 7.85 (d, J = 8.6 Hz, 1H), 7.82 – 7.76 (m, 2H),
7.56 – 7.40 (m, 3H). 13C NMR (100 MHz, CDCl3) δ 159.85,
152.19, 138.50, 135.50, 132.39, 132.21, 130.41, 129.60, 128.49,
128.16, 123.04, 121.80, 100.57. HRMS (ESI) calcd for
+
25 C15H9Br2O2 : 378.8964 (M++H), found: 378.8969
4-Iodo-3-phenyl-1H-isochromen-1-one (4h)4a (65.4 mg, 94%)
1H NMR (400 MHz, CDCl3) δ 8.29 (d, J = 7.9 Hz, 1H), 7.92 –
7.85 (m, 1H), 7.85 – 7.76 (m, 1H), 7.73 – 7.64 (m, 2H), 7.61 –
30 7.52 (m, 1H), 7.51 – 7.42 (m, 3H). 13C NMR (100 MHz, CDCl3)
δ 161.54, 154.76, 146.33, 138.14, 135.71, 135.20, 131.51, 130.18,
129.97, 129.72, 129.25, 128.08, 120.23.
5. Bronst acid-triggered cyclization of o-alkynylbenzoates: (a) M.
Hellal, J.-J. Bourguignon, and F. J.-J. Bihel, Tetrahedron
Lett. 2008, 49, 62; (b) M. Jacubert, O. Provot, J.-F. Peyrat, A.
Hamze, J.-D. Brion, and M. Alami, Tetrahedron 2010, 66,
3775; (c) M. Jacubert, A. Hamze, O. Provot, J.-F. Peyrat, J.-
D. Brion, and M. Alami, Tetrahedron Lett. 2009, 50, 3588;
(d) G. Le Bras, A. Hamze, S. Messaoudi, O. Provot, P.-B.
Le Calvez, J.-D. Brion, and M. Alami, Synthesis 2008, 1607.
6. Lewis acid-triggered cyclization of o-alkynylbenzoates: (a) D.
J. Faizi, A. Issaian, A. J. Davis, and S. A. Blum, J. Am.
Chem. Soc. 2016, 138, 2126; (b) A. Speranca, B. Godoi, S.
Pinton, D. Back, P. Menezes, and G. Zeni, J. Org. Chem.
2011, 76, 6789; (c) A. Nagarajan, and T. R.
Balasubramanian, Indian J. Chem., Section B: Org. Chem.
Including Med. Chem. 1987, 26B, 917; (d) Z. Li, J. Hong, L.
Weng, and X. Zhou, Tetrahedron 2012, 68, 1552; (e) K.
Komeyama, K. Takahashi, and K. Takaki, Org. Lett. 2008,
10, 5119.
7. Transitonal metal-catalyzed cyclization of o-alkynylbenzoates:
(a) Y. Liang, Y.-X. Xie, and J.-H. Li, Synthesis 2007, 400;
(b) M. Jithunsa, M. Ueda, and O. Miyata, Org. Lett. 2011,
13, 518; (c) T. Sugioka, E. Yoneda, K. Onitsuka, S.-W.
Zhang, and S. Takahashi, Tetrahedron Lett. 1997, 38, 4989;
(d) H. Wang, X. Han, and X. Lu, Tetrahedron 2013, 69,
8626; d) P. Zhang, D. Chen, G. Song, K. He, and X. Li, J.
Org. Chem. 2012, 77, 1579; (e) J. Zhang, X. Han, and X. Lu,
J. Org. Chem. 2016, 81, 3423; (f) W.-R. Chang, Y.-H. Lo,
C.-Y. Lee, and M.-J. Wu, Adv. Synth. Catal. 2008, 350,
1248.
4-Chloro-3-phenyl-1H-isochromen-1-one (4i)7b (33.4 mg, 65%)
35 1H NMR (400 MHz, CDCl3) δ 8.36 (d, J = 7.9 Hz, 1H), 7.97 (d, J
= 8.1Hz, 1H), 7.90 – 7.81 (m, 3H), 7.66– 7.58 (m, 1H), 7.56 –
7.43 (m, 3H). 13C NMR (100 MHz, CDCl3) δ 160.91, 150.40,
135.93, 135.33, 131.40, 130.19, 129.83, 129.32, 129.11, 128.20,
124.03, 120.49, 111.29.
40
Financial supports from the Natural Science Foundation of
China (Nos: 21502069 and 21502075), the Natural Science
Foundation of Zhejiang Province (Nos: LY14B02008 and
LQ15B020006), the Ph.D. Scientific Research Starting
45 Foundation of Jiaxing University (No: 70515015) and
Summit Program of Jiaxing University for Leading Talents
are gratefully acknowledged.
Notes and references
a.
School of Metallurgical and Chemical Engineering, Jiangxi
8. (a) Y. Li, G. Li, and Q. Ding, Eur. J. Org. Chem. 2014, 5017;
(b) G. Dai, J. Chang, J. Luo, S. Dong, N. Aratani, B. Zheng,
K.-W. Huang, H. Yamada, and C. Chi, Angew. Chem., Int.
Ed. 2016, 55, 2693; (c) M. Alami, F. Liron, M. Gervais, J.-F.
Peyrat, and J.-D. Brion, Angew. Chem., Int. Ed. 2002, 41,
1578; (d) H. Kusama, H. Funami, and N. Iwasawa, Synthesis
2007, 2014; (e) H. Kusama, H. Funami, J. Takaya, and N.
Iwasawa, Org. Lett. 2004, 6, 605
50 University of Science and Technology, 86 Hongqi Road, Ganzhou 341000,
China; Email: liujbgood@hotmail.com
b.
College of Biological, Chemical Science and Engineering, Jiaxing
University, 118 Jiahang Road, Jiaxing 314001, China. Email:
11110220028@fudan.edu.cn (G. Qiu)
55 † Electronic Supplementary Information (ESI) available: [Experimental
procedure, characterization data, 1H and 13C NMR spectra of compounds 3 and
4. See DOI: 10.1039/b000000x/
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