Please do not adjust margins
Page 5 of 6
Organic & Biomolecular Chemistry
Journal Name COMMUNICATION
DOI: 10.1039/C9OB00320G
General procedure for the synthesis of compound 4: N-Phenyl-2-
alkynylbenzamide 1 (0.2 mmol), TBAB (0.1 equiv), oxone (2.0
equiv), K2CO3 (3.0 equiv) were added to a test tube, and then solvent
THF:H2O (v/v = 1:1, 2.0 mL) was added. The mixture was stirred at
80 oC overnight. After the disappearance of substrate as indicated by
TLC, the mixture was filtrated and the resulting filtrate was
extracted by EA (3 * 2 mL). The organic layers were combined and
dried by Na2SO4. Then filtration again, evaporation of the solvent
and purification by flash column chromatograph provided the
desired products 4.
and X. Xu, Green. Chem. 2018, 20, 3683; (h) Y. Zheng, M.
Liu, G. Qiu, W. Xie, and J. Wu. Tetrahedron 2019, 75, 1663;
(i) Y. Zong, Y. Lang, M. Yang, X. Li, X. Fan, and J. Wu,
Org. Lett. 2019, 21, doi: 10.1021/acs.orglett.9b00620; (j) X.
Gong, J. Chen, X. Li, W. Xie, and J. Wu, Chem. Asian. J
2018, 13, 2543
.
2
5-exo-dig N-attacked cyclization of o-alkynylbenzamide: (a) D.
Y. Li, K. J. Shi, X. F. Mao, Z. L. Zhao, X. Y. Wu, and P. N.
Liu, Tetrahedron, 2014, 70, 7022; (b) J. Hu, X. Wang, Y.
Hu, S. Yang, and Y. Liang, Green Substainable Chem. 2011,
(Z)-N,3-diphenyl-1H-isochromen-1-imine (2a) (41.6 mg, 70%)
1H NMR (400 MHz, CDCl3) δ 8.40 (d, J = 7.9 Hz, 1H), 7.61 - 7.51
(m, 3H), 7.46 - 7.37 (m, 3H), 7.37 - 7.30 (m, 4H), 7.30 - 7.23 (m,
2H), 7.15 (t, J = 7.4 Hz, 1H), 6.72 (s, 1H);13C NMR (100 MHz,
CDCl3) δ 151.7, 149.8, 146.7, 133.9, 132.5, 132.3, 129.4, 128.7,
128.7, 128.2, 127.5, 125.6, 124.6, 123.6, 122.4, 100.9; HRMS (ESI)
calcd for C21H16NO+: 298.1226 (M++H), found: 298.1225
1
, 165; (c) C. Kanazawa and M. Terada, Asian. J. Chem.,
2009, , 1668; (d) D. Brahmchari, A. K. Akhilesh, and S.
Mehta, J. Org. Chem. 2018, 83, 3339; (e) J. Tan, Y. Tong,
and Z. Chen, Chemistryselect 2018, , 3886; (f) C. Wu, J.
4
3
Wang, X.-Y. Zhang, G.-K. Jia, Z. Cao, Z. Tang, X. Yu, X.
Xu, and W.-M. He, Org. Biomol. Chem. 2018, 16, 5050
6-endo-dig O-attacked cyclization of 2-alkynylbenzamide: (a)
Y. Madich, R. Alvarez, and J. M. Aurrecoechea, Eur. J. Org.
Chem., 2015, 6298; (b) M. Bian, W. Yao, H. Ding, and C.
Ma, J. Org. Chem., 2010, 75, 269; (c) G. Bianchi, M.
Chiarini, F. Marinelli, L. Rossi, and A. Arcadi, Adv. Syn.
Catal. 2010, 352, 136; (d) R. Alvarez, C. Martinez, Y.
Madich, J. G. Denis, J. M. Aurrecoechea, and A. R. de Lera,
Eur. J. Chem., 2010, 16, 12746; (e) G. Liu, D. Ye, D. Zhang,
3
3-phenyl-1H-isochromen-1-one (3a) (white solid, 34.6 mg,
78%)9a,10b
1H NMR (400 MHz, CDCl3) δ 8.30 (d, J = 8.2 Hz, 1H), 7.90 - 7.85
(m, 2H), 7.74 - 7.68 (m, 1H), 7.51 - 7.48 (m, 2H), 7.47-7.45 (m, 1H),
7.45 - 7.41 (m, 2H), 6.95 (s, 1H); 13C NMR (100 MHz, CDCl3) δ
162.3, 153.6, 137.5, 134.9, 131.9, 129.9, 129.6, 128.8, 128.2, 126.0,
125.2, 120.5, 101.8
X. Ding, H. Jiang, and H. Liu, Adv. Synth. Catal., 2009, 351
,
2605; (f) D. Ding, T. Mou, J. Xue, and X. Jiang, Chem.
Commun., 2017, 53, 5279; (g) X. Fu, Y. Meng, X. Li, M.
(Z)-N-phenyl-3-methyleneisobenzofuran-1-imine (4a) (38.1 mg,
86%)
Stepien, and P. J. Chemielewski, Chem. Commun. 2018, 54
,
1H NMR (400 MHz, CDCl3) δ 7.95 - 7.90 (m, 1H), 7.79 - 7.73 (m,
1H), 7.67 - 7.61 (m, 1H), 7.59 - 7.48 (m, 3H), 7.44 - 7.34 (m, 3H),
2510; (h) X. Li, B. Liu, P. J. Chmielewski, X. Xu, J. Org.
Chem. 2012, 77, 8206
5.24 - 7.21 (m, 1H), 4.82 - 4.78 (m, 1H); 13C NMR (100 MHz, 4 (a) J. S. S. Neto, D. F. Back, and G. Zeni, Eur. J. Org. Chem.,
CDCl3) δ 166.7, 143.1, 136.2, 134.5, 132.3, 129.8, 129.3, 128.9,
128.1, 128.0, 123.6, 120.0, 90.5; HRMS (ESI) calcd for C15H12NO+:
222.0913 (M++H), found: 222.0913
2015, 1583; (b) S. Mehta, T. Yao, and R. C. Larock, J. Org.
Chem., 2012, 77, 10938; (c) C. Schlemmer, L. Andernach, D.
Schollmeyer, B. F. Straub, and T. Opatz, J. Org. Chem., 2012,
77, 10118; (d) S. Mehta, J. P. Waldo, and R. C. Larock, J. Org.
Chem., 2009, 74, 1141; (e) B. S. Chinta, H. Sanapa, K. P.
Vasikarla, and B. Baire, Org. Biomol. Chem. 2018, 16, 3947;
5 (a) X. Zhang, C. Yang, D. Zhang-Negrerie, and Y. Du, Chem.
Eur. J., 2015, 21, 5192; (b) T. M. Ha, B. Yao, Q. Wang, and
Acknowledgement
Financial supports from the Natural Science Foundation of
China (Nos: 21502069, 21502075 and 21772067), the Natural
Science Foundation of Zhejiang (LY19B020004), China
postdoctoral science foundation (2018M630396) and the
program of Qingjiang Excellent Young Talents of JXUST (No.
JXUSTQJYX2017004) is gratefully acknowledged.
J. Zhu, Org. Lett., 2015,
7, 1750; (c) K. Dev and R. Maurya,
RSC Adv., 2015, , 13102; (d) J. Dong, F. Wang, and J. You,
5
Org. Lett., 2014, 16, 2884; (e) B. Yao, Q. Wang, and J. Zhu,
Angew. Chem., Int. Ed., 2012, 51, 5170; (f) Y. Luo and J.
Wu, Chem. Commun., 2011, 47, 11137; (g) D. Ding, G. Zhu,
and X. Jiang, Angew. Chem. Int. Ed. 2018, 57, 9028;
Notes and references
6 Transitional metal-catalyzed 5-exo-dig O-attacked cyclization
of 2-alkynylbenzamide, see: (a) Y. Madich, R. Alvarez, and
J. M. Aurrecoechea, Eur. J. Org. Chem., 2014, 6263; (b) M.
Jithunsa, M. Ueda and O. Miyata, Org. Lett., 2011, 13, 518; (c)
R. Mancuso, I. Ziccarelli, D. Armentano, N. Marino, S. V.
Giofre, and B. Gabriele, J. Org. Chem., 2014, 79, 3506; (d) B.
1 For selected reviews on synthetic applications using dual-
functionalized synthons, 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) M. Pirnot, Y.-
M. Wang, and S. Buchwald, Angew. Chem., Int. Ed., 2016,
Yao, C. Jaccoud, Q. Wang, J. Zhu, Eur. J. Chem., 2012, 18
,
5864; (e) Z.-Y. Yan, C.-M. Tan, X. Wang, F. Li, G.-L. Cao,
X.-M. Chen, W.-S. Wu, and J.-J. Wang, Synlett, 2011, 1863; (f)
X. Bantreil, A. Bourderioux, P. Mateo, C. E. Hagerman, M.
Selkti, E. Brachet, and P. Belmont, Org. Lett., 2016, 18, 4814;
55, 48; (d) A. Fuerstner, Angew. Chem., Int. Ed., 2013, 52
,
2794. Examples, see: (e) C. Wu, Z. Wang, Z. Hu, F. Zeng,
X.-Y. Zhang, Z. Cao, Z. Tang, W.-M. He, and X.-H. Xu,
Org. Biomol. Chem. 2018, 16, 3177; (f) L. –Y. Xie, S. Peng,
F. Liu, J.-Y. Yi, M. Wang, Z. Tang, X. Xu, and W.-M He,
This journal is © The Royal Society of Chemistry 20xx
J. Name., 2013, 00, 1-3 | 5
Please do not adjust margins