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The Journal of Organic Chemistry
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(10) (a) Wang, X.; Lerchen, A.; Glorius, F. Org. Lett.
Notes
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2016, 18, 2090. (b) Wang, X.; Jiao, N. Org. Lett.
2016, 18, 2150. (c) Wang, J.; Zha, S.; Chen, K.;
Zhang, F., Song, C.; Zhu, J. Org. Lett. 2016, 18, 2062.
(d) Yuan, H.; Yoo, W. J.; Miyamura, H.; Kobayashi,
S. Adv. Synth. Catal. 2012, 354, 2899. (e) Chen, M.
M.; Zhang, M.; Xiong, B.; Tan, Z. D.; Lv, W.; Jiang,
H. F. Org. Lett. 2014, 16, 6028. (f) Gopalaiah, K.;
Anupama Saini, A.; Devi , A. Org. Biomol. Chem.
2017, 15, 5781.
(11) For a recent review on ironꢀcatalyzed CꢀH bond
activation, see: Shang, R.; Ilies, L.; Nakamura, E.
Chem. Rev., 2017, 117, 9086.
(12) For a review on ironꢀcatalyzed synthesis of hetꢀ
erocycles, see: Krishna C. Majumdar, K. C.; Nirupam
De, N.; Tapas Ghosh, T.; Brindaban Roy, B. Tetraheꢀ
dron 2014, 70, 4827.
(13) (a) An ironꢀcatalyzed oxidative cyanation of terꢀ
tiary amines has been reported: Han W.; Ofial, A. R.
Chem. Commun. 2009, 5024. (b) For an efficient aerꢀ
obic oxidative synthesis of 2ꢀaryl quinazolines via
benzyl C–H bond amination catalyzed by 4ꢀhydroxyꢀ
TEMPO, see: Han, B.; Wang, C.; Han, R.ꢀF.; Yu, W.;
Duan, X.ꢀY.; Fang, R.; Yang, X.ꢀL. Chem. Commun.
2011, 47, 7818. (c) For a review on ironꢀcatalyzed Cꢀ
H oxidations; see; Jia, F.; Li, Z. Org. Chem. Front.
2014, 1, 194. (d) Li, Z.; Yu, R.; Li, H. Angew. Chem.
Int. Ed. 2008, 47, 74977. (e) Liu,W.; Liu, J.; Ogawa,
D.; Nishihara, Y.; Guo, X.; Li, Z. Org. Lett. 2011, 13,
6272. (f) Li, H.; He,Z.; Guo, X.; Li, W.; Zhao X.; Li,
Z. Org. Lett. 2009, 11, 4176.
The authors declare no competing financial interꢀ
est.
ACKNOWLEDGMENT
We would like to acknowledge Mrs. Huawei Ma
and Mrs. Jingjing Shi at Porton (Shanghai) R&D
Center for analytical supports. We also
acknowledge Mr. Peter J. Yao of Janssen R&D at
Cilag AG for helpful discussions during the prepꢀ
aration of this manuscript.
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REFERENCES
(1) (a) Khan, I.; Ibrar, A.; Ahmed, W.; Saeed, A. Eur.
J. Med. Chem. 2015, 90, 124. (b) Alam, M. J.; Alam,
O.; Naim, M. J.; Alam, P. Int. J. Adv. Res. 2015, 3,
1656. (c) Wang D.; Gao, F. Chem. Cent. J. 2013, 7, 1.
(2) For a review on quinazoline marketed drugs, see:
Selvam, T. P.; Kumar P. V. Res. in Pharm. 2011, 1, 1.
(3) (a) Lu, J.; Zhan, X.; Chen, L.; Zhang, L.; Mao, S.
J. Chem. Eng. Data 2014, 59, 2665. (b) Zhang, Y.;
Tortorella, M. D.; Liao, J.; Qin, X.; Chen, T.; Luo, J.;
Guan, J.; Talley, J. J.; Tu, Z. ACS Med. Chem. Lett.
2015, 6, 1086. (c) Duncton, M. A.; Estiarte, J. M. A.;
Johnson, R. J.; Cox, M.; O'Mahony, D. J. R.; Edꢀ
wards, W. T.; Kelly, M. G. J. Org. Chem. 2009, 74,
6354. (d) Zeng, Q.; Wang, J.; Cheng, Z.; Chen, K.;
Johnström, P.; Varnäs, K.; Li, D. Y.; Yang, Z. F.;
Zhang, X. J. Med. Chem. 2015, 58, 8200.
(4) Minkovsky, N., Berezov, A. Curr. Opin. Investig.
Drugs 2008, 9, 1336.
(5) Amer, M. S.; Browder, H. P. Proc. Soc. Exp. Biol.
Med. 1971, 136, 750.
(6) Gunasekara, N. S.; Faulds, D. Drugs 1998, 55,
423.
(7) Hoegenauer, K.; Soldermann, N.; Stauffer, F.;
Furet, P.; Graveleau, N.; Smith, A. B.; Hebach, C.;
Hollingworth, G. J.; Lewis, I.; Gutmann, S.; Rummel,
G.; Knapp, M.; Wolf, R. M.; Blanz, J.; Feifel, R.;
Burkhart, C.; Zécri, F. ACS Med. Chem. Lett. 2016,
7, 762.
(8) (a) Khan, I.; Zaib, S.; Batool, S.; Abbas, N.; Ashꢀ
raf, Z.; Iqbal, J.; Saeed, A. Bioorg. Med. Chem. 2016,
24, 2361.
(14) Chen, C.ꢀy.; Tang, G.; He, F.; Wang, Z.; Jing, H.;
Faessler, R. Org. Lett. 2016, 18, 1690.
(15) Quazodine was prepared from 1ꢀ(2ꢀaminoꢀ4,5ꢀ
dimethoxyphenyl)ꢀpropanone and DMF in 55% yield:
Byford, A.; Goadby, P.; Hooper, M.; Kamath, H. V.;
Kulkarni, Sheshgiri N. Indian J. Chem. 1988, 27B,
396.
(16) Compound 15j was employedd as a precursor to
the axially chiral quinazolineꢀcontaining ligands and
was prepared in 53% yield via a Suzuki coupling reꢀ
action, see: Connolly, D. J.; Lacey, P. M.; McCarthy,
M.; Saunders: C. P.; Carroll,A.ꢀM.; Goddard, R.;
Guiry, P. J. J. Org. Chem. 2004, 69, 6572.
(17) Bergman, J.; Brynolf, A.; Vuorinen, E.
Tetrahedron 1986, 42, 3689.
(18) Yang, T.; Zhu, H.; Yu, W. Org. Biomol. Chem.
2016, 14, 3376.
(19) Likhar, P. R.; Arundhathi, R.; Kantam, M. L.;
Prathima, P. S. Eur. J. Org. Chem. 2009, 31, 5383.
(20) Hikawa, H.; Koike, T.; Izumi, K.; Kikkawa, S.;
Azumaya, I. Adv. Synth. Catal. 2016, 358, 784.
(b) Kikelj, D. Product class 13:
quinazolines. Sci. Synth. 2004, 16, 573.
(9) For recent examples, see: (a) Mani Ramanathan,
M.; Liu, S.ꢀT. J. Org. Chem. 2017, 82, 8290 and refꢀ
erences cited therein. (b) Zhang, Z.ꢀH.; Zhang, X.ꢀN.;
Mo, L.ꢀP.; Li, Y.ꢀX.; Ma, F.ꢀP. Green Chem. 2012,
14, 1502. (c) Yao, S.; Zhou, K.; Wang, J.; Cao, H.;
Yu, L.; Wu, J.; Qiu, P.; Xu, Q. Green Chem. 2017,
19, 2945.
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