COMMUNICATIONS
KI-Catalyzed Three-Component Synthesis of 2-Arylquinazolines
tube at 908C. After 4 h, the remaining 70% aqueous TBHP
(82 mL, 0.6 mmol) was added, and then, the reaction mixture
was stirred at 908C for another 20 h. After the reaction had
finished, the reaction mixture was cooled to room tempera-
ture and then directly purified by flash column chromatogra-
phy on silica gel (petroleum ether:ethyl acetate=50:1–30:1)
to afford the desired product 3.
Synthesis of Products 3ia–ja: To a solution of 2-amino-
phenyl ketone 1 (0.3 mmol) in 1.5 mL toluene and 0.5 mL
DMSO were added NH4OAc (70 mg, 0.9 mmol) and FeCl3
(5 mg, 0.03 mmol), followed by 70% aqueous TBHP
(164 mL, 1.2 mmol). Then the Schlenk tube was charged
with N2, and the reaction mixture was stirred at 1008C for
24 h. After the reaction had finished, the reaction mixture
was cooled to room temperature and diluted with ethyl ace-
tate, then washed with brine. The aqueous layers were ex-
tracted with ethyl acetate (3ꢂ5 mL), the combined organic
layers were dried over Na2SO4 and evaporated under
vacuum. The residue was then purified by flash column
chromatography on silica gel (petroleum ether:ethyl ace-
tate=50:1–30:1) to afford the desired product 3.
[4] For recent examples, see: a) R. Vanjari, T. Guntreddi,
K. N. Singh, Org. Lett. 2013, 15, 4908; b) D. L. Priebbe-
now, C. Bolm, Org. Lett. 2014, 16, 1650; c) N. Wang, R.
Li, L. Li, S. Xu, H. Song, B. Wang, J. Org. Chem. 2014,
79, 5379; d) Y. Nishioka, T. Uchida, T. Katsuki, Angew.
Chem. 2013, 125, 1783; Angew. Chem. Int. Ed. 2013, 52,
1739; e) Q. Xue, J. Xie, H. Li, Y. Cheng, C. Zhu, Chem.
Commun. 2013, 49, 3700; f) W. Xiao, J. Wei, C.-Y.
Zhou, C.-M. Che, Chem. Commun. 2013, 49, 4619; g) J.
Ramon Suarez, J. Luis Chiara, Chem. Commun. 2013,
49, 9194; h) X. Zhang, M. Wang, P. Li, L. Wang, Chem.
Commun. 2014, 50, 8006.
[5] For selected examples, see: a) W. Liu, J. T. Groves,
Angew. Chem. 2013, 125, 6140; Angew. Chem. Int. Ed.
2013, 52, 6024; b) J.-B. Xia, C. Zhu, C. Chen, J. Am.
Chem. Soc. 2013, 135, 17494; c) K. L. Hull, W. Q.
Anani, M. S. Sanford, J. Am. Chem. Soc. 2006, 128,
7134.
[6] a) C. Chen, X.-H. Xu, B. Yang, F.-L. Qing, Org. Lett.
2014, 16, 3372; b) B. Du, B. Jin, P. Sun, Org. Lett. 2014,
16, 3032.
[7] F. Kakiuchi, K. Tsuchiya, M. Matsumoto, B. Mizushi-
ma, N. Chatani, J. Am. Chem. Soc. 2004, 126, 12792.
[8] a) M. Ichinose, H. Suematsu, Y. Yasutomi, Y. Nishioka,
T. Uchida, T. Katsuki, Angew. Chem. 2011, 123, 10058;
Angew. Chem. Int. Ed. 2011, 50, 9884; b) P. Novak, A.
Correa, J. Gallardo-Donaire, R. Martin, Angew. Chem.
2011, 123, 12444; Angew. Chem. Int. Ed. 2011, 50,
12236; c) C. Tsukano, M. Okuno, Y. Takemoto, Angew.
Chem. 2012, 124, 2817; Angew. Chem. Int. Ed. 2012, 51,
2763; d) G. Pandey, S. Pal, R. Laha, Angew. Chem.
2013, 125, 5250; Angew. Chem. Int. Ed. 2013, 52, 5146;
e) Y. Minami, K. Yamada, T. Hiyama, Angew. Chem.
2013, 125, 10805; Angew. Chem. Int. Ed. 2013, 52,
10611; f) Y. R. Kim, S. Cho, P. H. Lee, Org. Lett. 2014,
16, 3098; g) Y. Li, Z. Li, T. Xiong, Q. Zhang, X. Zhang,
Org. Lett. 2012, 14, 3522; h) D. Eom, Y. Jeong, Y. R.
Kim, E. Lee, W. Choi, P. H. Lee, Org. Lett. 2013, 15,
5210.
Acknowledgements
This work was supported by the National Natural Science
Foundation of China (21272114, 91313303), and the National
Natural Science Fund for Creative Research Groups
(21121091).
References
[1] For reviews, see: a) S. A. Girard, T. Knauber, C. J. Li,
Angew. Chem. 2014, 126, 76; Angew. Chem. Int. Ed.
2014, 53, 74; b) B.-J. Li, Z.-J. Shi, Chem. Soc. Rev. 2012,
41, 5588.
[9] a) T. Xiong, Y. Li, X. Bi, Y. Lv, Q. Zhang, Angew.
Chem. 2011, 123, 7278; Angew. Chem. Int. Ed. 2011, 50,
7140; b) L. Gu, C. Jin, J. Guo, L. Zhang, W. Wang,
Chem. Commun. 2013, 49, 10968; c) T. Nanjo, C. Tsu-
kano, Y. Takemoto, Org. Lett. 2012, 14, 4270.
[10] D. Zhao, T. Wang, J.-X. Li, Chem. Commun. 2014, 50,
6471.
[11] For reviews, see: a) A. Witt, J. Bergman, Curr. Org.
Chem. 2003, 7, 659; b) J. P. Michael, Nat. Prod. Rep.
2008, 25, 166.
[12] For reviews, see: a) I. Khan, A. Ibrar, N. Abbas, A.
Saeed, Eur. J. Med. Chem. 2014, 76, 193; b) D. J. Con-
nolly, D. Cusack, T. P. OꢀSullivan, P. J. Guiry, Tetrahe-
dron 2005, 61, 10153.
[13] a) C. U. Maheswari, G. S. Kumar, M. Venkateshwar,
R. A. Kumar, M. L. Kantam, K. R. Reddy, Adv. Synth.
Catal. 2010, 352, 341; b) H. Yuan, W.-J. Yoo, H. Miya-
mura, S. Kobayashi, Adv. Synth. Catal. 2012, 354, 2899;
c) B. Han, X.-L. Yang, C. Wang, Y.-W. Bai, T.-C. Pan,
X. Chen, W. Yu, J. Org. Chem. 2012, 77, 1136.
[2] For recent examples, see: a) B. Schweitzer-Chaput, A.
Sud, A. Pinter, S. Dehn, P. Schulze, M. Klussmann,
Angew. Chem. 2013, 125, 13470; Angew. Chem. Int. Ed.
2013, 52, 13228; b) Y. N. Wu, P. Y. Choy, F. Mao, F. Y.
Kwong, Chem. Commun. 2013, 49, 689; c) M.-B. Zhou,
C.-Y. Wang, R.-J. Song, Y. Liu, W.-T. Wei, J.-H. Li,
Chem. Commun. 2013, 49, 10817; d) S.-L. Zhou, L.-N.
Guo, S. Wang, X.-H. Duan, Chem. Commun. 2014, 50,
3589; e) H. Yang, H. Yan, P. Sun, Y. Zhu, L. Lu, D.
Liu, G. Rong, J. Mao, Green Chem. 2013, 15, 976; f) F.
Xiong, C. Qian, D. Lin, W. Zeng, X. Lu, Org. Lett.
2013, 15, 5444.
[3] For recent examples, see: a) J. Feng, S. Liang, S.-Y.
Chen, J. Zhang, S.-S. Fu, X.-Q. Yu, Adv. Synth. Catal.
2012, 354, 1287; b) G. Majji, S. Guin, A. Gogoi, S. K.
Rout, B. K. Patel, Chem. Commun. 2013, 49, 3031;
c) S. K. Rout, S. Guin, W. Ali, A. Gogoi, B. K. Patel,
Org. Lett. 2014, 16, 3086; d) H. Liu, G. Shi, S. Pan, Y.
Jiang, Y. Zhang, Org. Lett. 2013, 15, 4098; e) S. K.
Rout, S. Guin, K. K. Ghara, A. Banerjee, B. K. Patel,
Org. Lett. 2012, 14, 3982; f) S. K. Rout, S. Guin, A.
Banerjee, N. Khatun, A. Gogoi, B. K. Patel, Org. Lett.
2013, 15, 4106.
[14] a) Z. Chen, J. Chen, M. Liu, J. Ding, W. Gao, X.
Huang, H. Wu, J. Org. Chem. 2013, 78, 11342; b) L. Ye,
L. Yu, L. Zhu, X. Xia, Molecules 2013, 18, 13860.
Adv. Synth. Catal. 0000, 000, 0 – 0
ꢁ 2014 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
5
ÞÞ
These are not the final page numbers!