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ChemComm
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COMMUNICATION
Journal Name
transition-metal catalyst without the use of an additional (11) (a) Z. Ma, Y. Hano, T. Nomura, Heterocycles 2005, 65, 2203;
initiator/oxidant. This transformation produced a broad range of
DOI: 10.1039/C9CC06160F
(b) J. L. Liang, H. C. Cha, Y. Jahng, Molecules 2011, 16, 4861.
quinazolinones as well as fused quinazolinones in good to excellent
yields under simple reaction conditions. Applying this strategy, a
concise synthesis of Rutaecarpine and its derivatives has been
accomplished without muti-steps process. Further studies to
understand the mechanism for the reaction are currently underway
in our laboratory.
We thank Jiangsu Key Laboratory of Advanced Catalytic Materials
and Technology (BM2012110), Advanced Catalysis and Green
Manufacturing Collaborative Innovation Center in Changzhou
University.
(12) (a) A. Ibric, S. Eckerstorfer, M. Eder, I. Louko, L. Tunjic, P.
Heffeter, H. H. Schueffl, B. Marian, N. Haider,
Molecules 2019, 24, 716; (b) A. Cagir, S. H. Jones, R. Gao, B. M.
Eisenhauer, S. M. Hecht, J. Am. Chem. Soc. 2003, 125, 13628;
(c) V. Gonzalez-Ruiz, I. Pascua, T. Fernandez-Marcelo, P.
Ribelles, G. Bianchini, V. Sridharan, P. Iniesta, M. T. Ramos, A.
I. Olives, M. A. Martin, J. C. Menendez, PLoS One 2014, 9,
e95998.
(13) (a) Y. Liu, W. Xu, X. Wang, Org. Lett. 2010, 12, 1448; (b) L.-N.
Liang, R. An, T. Huang, M. Xu, X.-J. Hao, W.-D. Pan, S. Liu,
Tetrahedron Lett. 2015, 56, 2466; (c) D. Nishiyama, A. Ohara,
H. Chiba, H. Kumagai, S. Oishi, N. Fujii, H. Ohno, Org. Lett. 2016,
18, 1670; (d) L. Zhang, Y. Wang, Z.-J. Yao, S. Wang, Z.-Y. Yu, J.
Am. Chem. Soc. 2015, 137, 13290; (e) S. Guven, M. S. Ozer, S.
Kaya, N. Menges, M. Balci, Org. Lett. 2015, 17, 2660; (f) X.-F.
Kong, F. Zhan, G.-X. He, C.-X. Pan, C.-X. Gu, K. Lu, D.-L. Mo, G.-F.
Su, J. Org. Chem. 2018, 83, 2006; (g) F. Xie, Q. Chen, R. Xie, H.
Jiang, M. Zhang, ACS Catal., 2018, 8, 5869; (h) C. Lu, Z. Su, D.
Jing, S. Jin, L. Xie, L. Li, K. Zheng, Org. Lett. 2019, 21, 1438.
(14) W. R. Bowman, M. R. J. Elsegood, T. Stein, G. W. Weaver, Org.
Biomol. Chem. 2007, 5, 103.
Notes and references
(1) (a) Y. Yamamoto, Chem. Soc. Rev. 2014, 43, 1575; (b) G. Albano,
L. A. Aronica, Eur. J. Org. Chem. 2017, 48, 7204; (c) G. Albano,
L. A. Aronica, Synthesis 2018, 50, 1209; (d) I. Muthukrishnan,
V. Sridharan, J. Carlos Menéndez, Chem. Rev. 2019, 119, 5057.
(2) (a) J. P. Michael, Nat. Prod. Rep. 2008, 25, 166; (b) J. P. Michael,
Nat. Prod. Rep. 2007, 24, 223; (c) S. B. Mhaske, N. P. Argade,
Tetrahedron 2006, 62, 9787; (d) D. J. Connolly, D. Cusack, T.
P. O’Sullivan, P. J. Guiry, Tetrahedron 2005, 61, 10153; (e) S.
Gatadi, T. V. Lakshmi, S. Nanduri, Eur. J. Med. Chem.
2019, 170, 157.
(3) (a) J. Bergman, S. Bergman, J. Org. Chem. 1985, 50, 1246; (b)
W. F. Chiou, J. F. Liao, C. F. Chen, J. Nat. Prod. 1996, 59, 374; (c)
Y. Li, T. Feng, P. Liu, C. Liu, X. Wang, D. Li, N. Li, M. Chen, Y. Xu,
S. Si, ACS Med. Chem. Lett. 2014, 5, 884; (d) J.-K. Son, H. W.
Chang, Y. Jahng, Molecules 2015, 20, 10800; (e) K.-M. Tian, J.-
J. Li, S.-W. Xu, Pharmacol. Res. 2019, 141, 541.
(4) (a) S. Jia, C. Hu, T. Jayakumar, J.-R. Sheu, J. Exp. Clin.
Med. 2011, 3, 63; (b) S. Jia, C. Hu, Molecules 2010, 15, 1873.
(5) (a) C. Lee, J. Liao, S. Chen, C. Yen, Y. Lee, S. Huang, S. Huang, C.
Lin, Front. Pharmacol. 2019, 10, 91; (b) G. Huang, A.
Drakopoulos, M. Saedtler, H. Zou, L. Meinel, J. Heilmann, M.
Decker, Bioorg. Med. Chem. Lett. 2017, 27, 4937; (c) Y.-H. Li, Y.
Zhang, L.-Y. Peng, X.-N. Li, Q.-S. Zhao, R.-T. Li, X.-D. Wu, Natur.
Prod. Bioprosp. 2016, 6, 291.
(6) (a) Y.-C. Chen, X.-Y. Zeng, Y. He, H. Liu, B. Wang, H. Zhou, J.-W.
Chen, P.-Q. Liu, L.-Q. Gu, J.-M. Ye, ACS Chem. Biol.
2015, 10, 1570; (b) Y.-C. Chen, X.-Y. Zeng, Y. He, H. Liu, B.
Wang, H. Zhou, J.-W. Chen, P.-Q. Liu, L.-Q. Gu, J.-M. Ye, ACS
Chem. Biol. 2013, 8, 2301.
(15) X. Pan, T. D. Bannister, Org. Lett. 2014, 16, 6124.
(16) C. Zhang, C. De Kanta, R. Mal, D. Seidel, J. Am. Chem. Soc. 2008,
130, 416.
(17) (a) L. Liu, J. Qiang, S. Bai, H.-L. Sung, C. Miao, J. Li, Adv. Synth.
Catal. 2017, 359, 1283; (b) J. Li, S. Bai, Y. Li, Z. Wang, X. Huo,
L. Liu, J. Org. Chem. 2018, 83, 8780; (c) L. Liu, S. Bai, Y. Li, X.-D.
Ding, Q. Liu, J. Li, Adv. Synth. Catal. 2018, 360, 1617; (d) L. Liu,
S. Bai, Y. Li, L.-X. Wang, Y. Hu, H.-L. Sung, J. Li, J. Org. Chem.
Morelli, M. Lissia, L. A. Aronica, ChemistrySelect 2019, 4, 2505.
(18) (a) H. Jin, L. Huang, J. Xie, M. Rudolph, F. Rominger, A.S.K.
Hashmi, Angew. Chem., Int. Ed. 2016, 55, 794; (b) S. Yu, G.
Tang, Y. Li, X. Zhou, Y. Lan, X. Li, Angew. Chem., Int. Ed. 2016,
55, 8696; (c) R. L. Sahani, R. S. Liu, Angew. Chem. Int. Ed. 2017,
56, 12736; (d) J. Li, E. Tan, N. Keller, Y.-H. Chen, P. M.
Zehetmaier, A. C. Jakowetz, T. Bein, P. Knochel, J. Am. Chem.
Soc. 2019, 141, 98; (e) Mokar, B. D.; Jadhav, P. D.; Pandit, Y. B.;
Liu. R.S. Chem. Sci. 2018, 9, 4488; (f) S. Kim, Han, S.H.; Mishra,
N. K.; Chun, R.; Jung, Y. H.; Kim, H. S.; Park, J. S.; Kim, I. S. Org.
Lett. 2018, 20, 4010.
(7) (a) T. Jayakumar, J.-R. Sheu, J. Exp. Clin. Med. 2011, 3, 63; (b)
J.-R. Sheu, Y.-C. Kan, W.-C. Hung, C.-H. Su, C.-H. Lin, Y.-M. Lee,
M.-H. Yen, Thromb. Res. 1998, 92, 53; (c) J. R. Sheu, W. C.
Hung, C. H. Wu, Br. J. Haematol, 2000, 110, 110; (d) J. R. Sheu,
Y. C. Kan, W. C. Hung, Thromb. Res, 1998, 92, 53.
(19) (a) K. A. Jensen, F. Friediger, Kgl. Danske Videnskab. Selskab,
Mat.-Fys. Medd. 1943, 20, 1; Chem. Zentr. 1944, I, 416; (b) T. R.
Matthew, B. Martin, Y. P. Alena, U. Anja, D. Arne, K. N. Houk, S.
Daniel, J. Am. Chem. Soc. 2014, 136, 6123.
[20] (a) G. Del Re, Tetrahedron1960, 10, 81; (b)G. Berthier, G. Del
Re, J . Chem. Sac. 1965, 3109.
[21] M. Decker, Eur. J. Med. Chem. 2005, 40, 305.
(8) (a) J. Ma, L. Chen, J. Fan, W. Cao, G. Zeng, Y. Wang, Y. Li, Y. Zhou,
X. Deng, Eur. J. Med. Chem. 2019, 168, 146; (b) Z. Chen, G. Hu,
D. Li, J. Chen, Y. Li, H. Zhou, Y. Xie, Bioorg. Med. Chem.
2009, 17, 2351; (c) C.-P. Hu, L. Xiao, H.-W. Deng, Y.-J. Li, Planta.
Medica. 2003, 69, 125.
(9) K. Huber, F. Bracher, Naturforsch., B., 2007, 62, 1313.
(10) Q. Liu, W. Zheng, H.-Y. Sang, J.-X. Chen, Chinese J. Med. Chem.
2006, 16, 20.
4 | J. Name., 2012, 00, 1-3
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