4
Tetrahedron
Mitobe, Y.; Ito, S.; Mizutani, T.; Nagase, T.; Sato, N.; Tokita, S.
Bioorg. Med. Chem. Lett. 2009, 19, 4075-4078.
1
1
2. Ge, W.; Zhu, X.; Wei, Y. RSC Adv. 2013, 3, 10817.
3. Sharif, M.; Opalach, J.; Langer, P.; Beller, M.; Wu, X.-F. RSC
Adv. 2014, 4, 8-17.
1
1
4. Kim, N. Y.; Cheon, C.-H Tetrahedron. Lett. 2014, 55, 2340-2344.
5. (a) Zhang, Z.; Wang, M.; Zhang, C.; Zhang, Z.; Lu, J.; Wang, F.
Chem. Commun. 2015, 51, 9205-7; (b) Zhao, D.; Zhou, Y.-R.;
Shen, Q.; Li, J.-X. RSC Adv. 2014, 4, 6486.
Scheme 3. Possible Reaction Process for the Synthesis of
Quinazolinones
quinazolinone in the presence of [V ] species. Simultaneously,
the generated [V ] species is converted to [V ] species with
2
assistance of O .
5+
16. Hu, Y.; Chen, L.; Li, B. RSC Adv. 2016, 6, 65196-65204.
4+
5+
17. (a) Zhou, J.; Fang, J. J. Org. Chem. 2011, 76, 7730-6; (b) Watson,
A. J.; Maxwell, A. C.; Williams, J. M. Org. Biomol. Chem. 2012,
1
0, 240-243; (c) Hikawa, H.; Ino, Y.; Suzuki, H.; Yokoyama, Y.
J. Org. Chem. 2012, 77, 7046-7051; (d) Hakim Siddiki, S. M. A.;
Kon, K.; Touchy, A. S.; Shimizu, K.-i. Catal. Sci. Technol. 2014,
Conclusion
4
1
, 1716; (e) Li, F.; Lu, L.; Ma, J. Org. Chem. Front. 2015, 2,
589-1597.
In conclusion, we reported a simple and efficient method for
the synthesis of quinazolinones using VO(acac) as the catalyst
2
1
1
2
8. (a) Wang, L.; Shang, S.; Li, G.; Ren, L.; Lv, Y.; Gao, S.
J. Org. Chem. 2016, 81, 2189-2193; (b) Wang, L.; Li, J.; Dai, W.;
Lv, Y.; Zhang, Y.; Gao, S., Green Chem. 2014, 16, 2164-2173; (c)
Wang, L.; Bie, Z.; Shang, S.; Lv, Y.; Li, G.; Niu, J.; Gao, S. RSC
Adv. 2016, 6, 35008-35013; (d) Wang, L.; Li, J.; Yang, H.; Lv, Y.;
Gao, S. J. Org. Chem. 2011, 77, 790-794.
9. (a) Hanson, S. K.; Baker, R. T.; Gordon, J. C.; Scott, B. L.; Silks,
L. P.; Thorn, D. L. J. Am. Chem. Soc. 2010, 132, 17804-17816;
(b) Velusamy, S.; Punniyamurthy, T. Org. Lett. 2004, 6, 217-219;
and environmentally friendly dioxygen as the oxidant. In this
protocol, diverse aldehydes and alcohols can be easily reacted
with a series of substituted 2-aminobenzamides under additive-
free conditions, and the corresponding quinazolinones were
obtained in good to excellent yields. The present protocol
provides an efficient and environmentally benign method for the
synthesis of quinazolinones, and it will attract much attention in
academic research and industrial applications.
(
c) Hanson, S. K.; Wu, R.; Silks, L. P. Org. Lett. 2011, 13, 1908-
1911; (d) Jiang, N.; Ragauskas, A. J. J. Org. Chem. 2007, 72,
7
030-7033.
Acknowledgments
0. Wang, L.; Chen, B.; Ren, L.; Zhang, H.; Lü, Y.; Gao, S. Chin. J.
Catal. 2015, 36, 19-23.
We gratefully acknowledge financial support from the
National Natural Science Foundation of China (No 21403219).
21. Du, Z.; Miao, H.; Ma, H.; Sun, Z.; Ma, J.; Xu, J. Adv. Synth. Catal.
2
009, 351, 558-562.
Supplementary Material
References and notes
1
2
.
.
(a) Mhaske, S. B.; Argade, N. P. Tetrahedron 2006, 62, 9787-
826; (b) Michael, J. P. Nat. Prod. Rep. 2004, 21, 650-668.
(a) Hour, M.-J.; Huang, L.-J.; Kuo, S.-C.; Xia, Y.; Bastow, K.;
Supplementary data (detailed experimental procedures, and
NMR of compounds) sociated with this article can be found, in
theonline version,
9
Nakanishi, Y.; Hamel, E.; Lee, K.-H. J. Med. Chem. 2000, 43,
4
479-4487; (b) Liverton, N. J.; Armstrong, D. J.; Claremon, D. A.;
Remy, D. C.; Baldvin, J. J.; Lynch, R. J.; Zhang, G.; Gould, R. J.
Bioorg. Med. Chem. Lett. 1998, 8, 483-486; (c) Khan, I.; Ibrar, A.;
Abbas, N.; Saeed, A. Eur. J. Med. Chem. 2014, 76, 193-244; (d)
Jain, K. S.; Bariwal, J. B.; Kathiravan, M. K.; Phoujdar, M. S.;
Sahne, R. S.; Chauhan, B. S.; Shah, A. K.; Yadav, M. R.
Bioorg. Med. Chem. 2008, 16, 4759-4800; (e) Ismail, M. A.;
Barker, S.; Abou El Ella, D. A.; Abouzid, K. A.; Toubar, R. A.;
Todd, M. H. J. Med. Chem. 2006, 49, 1526-1535.
3
.
(a) Sinha, S.; Srivastava, M. Prog. Drug. Res. 1994; pp 143-238;
(b) Arora, D.; Kumar, H.; Malhotra, D.; Malhotra, M.
Pharmacologyonline 2011, 3, 659-668; (c) Alagarsamy, V.; Raja
Solomon, V.; Sheorey, R.; Jayakumar, R. Chem. Biol. Drug. Des.
2
009, 73, 471-479.
4
.
(a) Horton, D. A.; Bourne, G. T.; Smythe, M. L. Chem. Rev.
2
003, 103, 893-930; (b) Connolly, D. J.; Cusack, D.; O'Sullivan,
T. P.; Guiry, P. J. Tetrahedron 2005, 61, 10153-10202; (c) He, L.;
Li, H.; Chen, J.; Wu, X.-F. RSC Adv. 2014, 4, 12065.
5
6
.
.
López, S.; Romero, A.; Salazar, J. Synthesis. 2013, 45, 2043-2050.
(a) Chen, X.; Chen, T.; Ji, F.; Zhou, Y.; Yin, S.-F. Catal. Sci.
Technol. 2015, 5, 2197-2202; (b) Mohammed, S.; Vishwakarma,
R. A.; Bharate, S. B. J. Org. Chem. 2015, 80, 6915-21; (c) Qi, X.-
X.; Song, Z.-Z.; Gong, J.-L.; Fang, Z.-Y.; Wu, X.-F.
Chin. Chem. Lett. 2016, 27, 21-24.
(a) Xu, W.; Jin, Y.; Liu, H.; Jiang, Y.; Fu, H. Org. Lett. 2011, 13,
7
.
1
274-1277; (b) Guo, S.; Li, Y.; Tao, L.; Zhang, W.; Fan, X. RSC
Adv. 2014, 4, 59289-59296.
Wan, C.; Zhang, J.; Wang, S.; Fan, J.; Wang, Z. Org. Lett. 2010,
8
9
1
.
.
1
2, 2338-41.
Li, H.; He, L.; Neumann, H.; Beller, M.; Wu, X.-F. Green Chem.
014, 16, 1336-1343.
0. (a) Liu, X.; Fu, H.; Jiang, Y.; Zhao, Y. Angew. Chem. 2009, 48,
48-51; (b) Zhang, X.; Ye, D.; Sun, H.; Guo, D.; Wang, J.; Huang,
2
3
H.; Zhang, X.; Jiang, H.; Liu, H. Green Chem. 2009, 11, 1881.
1. (a) Abdel-Jalil, R. J.; Voelter, W.; Saeed, M. Tetrahedron. Lett.
1
2
004, 45, 3475-3476; (b) Zheng, Y.; Bian, M.; Deng, X. Q.;
Wang, S. B.; Quan, Z. S. Arch. Pharm. 2013, 346, 119-126; (c)