Citation: Li Lingjie, Zhang Jing, Tang Yu, Xu Kaitian, Zhang Yuanming. Catalyst-Free One-Pot Synthesis of 4-Substituted Quinazolines[J]. Chinese Journal of Organic Chemistry, ;2017, 37(10): 2711-2716. doi: 10.6023/cjoc201705021 shu

Catalyst-Free One-Pot Synthesis of 4-Substituted Quinazolines

Department of Chemistry, College of Chemistry and Materials Science, Jinan University, Guangzhou 510632

Corresponding author: Tang Yu, tytang@jnu.edu.cn Zhang Yuanming, tzhangym@jnu.edu.cn
Received Date: 15 May 2017
Revised Date: 5 June 2017
Available Online: 16 October 2017
Fund Project: the National Natural Science Foundation of China 21274083Project supported by the National Natural Science Foundation of China (No. 21274083)

Figures(2)

A novel and catalyst-free one-pot method for the preparation of quinazoline compounds has been reported. Of the prepared 15 quinazoline compounds, three are new compounds. Their yields are among 37%~95%. The effects of electron effect and steric hindrance on the reaction were discussed. A plausible novel mechanism concerning repeating nucleophilic addition and elimination to give quinazoline has been proposed. By this mechanism, the reaction could be applied to acid anhydride instead of N, N-dimethylformamide (DMF).
- quinazoline,
- one-pot,
- catalyst-free,
- Grignard reagent,
- synthesis
1. [1]
  (a) Wattanapiromsakul, C.; Forster, P. I.; Waterman, P. G. Phytochemistry 2003, 64, 609.
  (b) Foster, B. A.; Coffey, H. A.; Morin, M. J.; Rastinejad, F. Science 1999, 286, 2507.
  (c) Doyle, L. A.; Ross, D. D. Oncogene 2003, 22, 7340.
  (d) Deng, Y.; Xu, R.; Ye, Y. Pharm. Sci. 2000, 9, 116.
2. [2]
  (a) El-Azab, A. S.; Al-Omar, M. A.; Alaa, A.-M.; Abdel-Aziz, N. I.; Magda, A.-A.; Aleisa, A. M.; Sayed-Ahmed, M. M.; Abdel-Hamide, S. G. Eur. J. Med. Chem. 2010, 45, 4188.
  (b) Henderson, E. A.; Bavetsias, V.; Theti, D. S.; Wilson, S. C.; Clauss, R.; Jackman, A. L. Bioorg. Med. Chem. 2006, 14, 5020.
  (c) Noolvi, M. N.; Patel, H. M.; Bhardwaj, V.; Chauhan, A. Eur. J. Med. Chem. 2011, 46, 2327.
  (d) Hou, X.; Zhang, J.; Zhao, X.; Chang, L.; Hu, P.; Liu. H. Chin. J. Chem. 2014, 32, 538.
3. [3]
  (a) Chien, T. C.; Chen, C. S.; Yu, F. H.; Chern, J. W. Chem. Pharm. Bull. 2004, 52, 1422.
  (b) Waisser, K.; Gregor, J.; Dostál, H.; Kuneš, J.; Kubicová, L.; Klimešová, V.; Kaustová, J. Farmaco 2001, 56, 803.
  (c) Herget, T.; Freitag, M.; Morbitzer, M.; Kupfer, R.; Stamminger, T.; Marschall, M. Antimicrob. Agents Ch emother. 2004, 48, 4154.
4. [4]
  (a) Kuneš, J.; Bažant, J.; Pour, M.; Waisser, K.; Šlosárek, M.; Janota, J. Farmaco 2000, 55, 725.
  (b) Kumar, A.; Sharma, P.; Kumari, P.; Kalal, B. L. Bioorg. Med. Chem. Lett. 2011, 21, 4353.
  (c) Balakumar, C.; Lamba, P.; Kishore, D. P.; Narayana, B. L.; Rao, K. V.; Rajwinder, K.; Rao, A. R.; Shireesha, B.; Narsaiah, B. Eur. J. Med. Chem. 2010, 45, 4904.
  (d) Alafeefy, A. M.; Kadi, A. A.; Al-Deeb, O. A.; El-Tahir, K. E.; Al-jaber, N. A. Eur. J. Med. Chem. 2010, 45, 4947.
5. [5]
6. [6]
  (a) Gilchrist, T. L. J. Chem. Soc., Perkin Trans. 1 1998, 3, 615.
  (b) Connolly, D. J.; Cusack, D.; O'Sullivan, T. P.; Guiry, P. J. Tetrahedron 2005, 61, 10153.
7. [7]
  (a) Panja, S. K.; Dwivedi, N.; Saha, S. Tetrahedron Lett. 2012, 53, 6167.
  (b) Yan, Y.; Xu, Y.; Niu, B.; Xie, H.; Liu, Y. J. Org. Chem. 2015, 80, 5581.
  (c) Bandaru, M.; Sabbavarapu, N. M.; Pavan, A. K.; Akula, A. K.; Durga, N. Y. V. Eur. J. Chem. 2012, 3, 252.
8. [8]
  (a) Han, B.; Wang, C.; Han, R.-F.; Yu, W.; Duan, X.-Y.; Fang, R.; Yang, X.-L. Chem. Commun. 2011, 47, 7818.
  (b) Zhang, J.; Yu, C.; Wang, S.; Wan, C.; Wang, Z. Chem. Commun. 2010, 46, 5244.
  (c) Zhang, J.; Zhu, D.; Yu, C.; Wan, C.; Wang, Z. Org. Lett. 2010, 12, 2841.
9. [9]
  Huang, C.; Fu, Y.; Fu, H.; Jiang, Y.; Zhao, Y. Chem. Commun. 2008, 44, 6333.
10. [10]
  Malakar, C. C.; Baskakova, A.; Conrad, J.; Beifuss, U. Chem.-Eur. J. 2012, 18, 8882. doi: 10.1002/chem.v18.29
11. [11]
  Yan, Y.; Wang, Z. Chem. Commun. 2011, 47, 9513. doi: 10.1039/c1cc12885j
12. [12]
  Duan, T.; Zhai, T.; Liu, H.; Yan, Z.; Zhao, Y.; Feng, L.; Ma, C. Org. Biomol. Chem. 2016, 14, 6561. doi: 10.1039/C6OB00625F
13. [13]
  Wen, Y.-M.; Chen, G.-F.; Tang, Y.; Chen. J.; Yang J.; Zhang, Y.-M. Chin. J. Org. Chem. 2015, 35, 2545.
14. [14]
  Maitraie, D.; Yakaiah, T.; Srinivas, K.; Reddy, G. V.; Ravikanth, S.; Narsaiah, B.; Rao, P. S.; Ravikumar, K.; Sridhar, B. J. Fluorine Chem. 2006, 127, 351. doi: 10.1016/j.jfluchem.2006.01.003
15. [15]
  Yang, C.-H.; Fang, K.-H.; Su, W.-L.; Wang, S.-P.; Su, S.-K.; Sun, I.-W. J. Organomet. Chem. 2006, 691, 2767. doi: 10.1016/j.jorganchem.2006.02.034
16. [16]
  Higashino, T.; Takemoto, M.; Hayashi, E. Chem. Pharm. Bull. 1985, 33, 1351. doi: 10.1248/cpb.33.1351
17. [17]
  Kita, Y.; Higashida, K.; Yamaji, K.; Iimuro, A.; Mashima, K. Chem. Commun. 2015, 51, 4380. doi: 10.1039/C5CC00258C
18. [18]
  Yang, Y. Synthesis 2016, 48, 2255. doi: 10.1055/s-00000084
19. [19]
  Yan, Y.; Zhang, Y.; Feng, C.; Zha, Z.; Wang, Z. Angew. Chem., Int. Ed. 2012, 51, 8077. doi: 10.1002/anie.v51.32
20. [20]
  Quattrini, M. C.; Fujii, S.; Yamada, K.; Fukuyama, T.; Ravelli, D.; Fagnoni, M.; Ryu, I. Chem. Commun. 2017, 53, 23358.
21. [21]
  Bergman, J.; Brynolf, A.; Elman, B.; Vuorinen, E. Tetrahedron 1986, 42, 3697. doi: 10.1016/S0040-4020(01)87338-5
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