Chinese Journal of Organic Chemistry >
Facile Synthesis of Benzoxazinone Derivatives via Palladium Catalyzed Intramolecular Amination
Received date: 2017-03-06
Revised date: 2017-04-08
Online published: 2017-04-21
Supported by
Project supported by the National Natural Science Foundation of China (No. 21572149) and the Young National Natural Science Foundation of China (Nos. 21402133, 21403148).
Benzoxazinone and its derivatives are well-known as a broad-spectrum of physiological activities compounds. Herein we report a novel approach for the synthesis of benzoxazine derivatives via a N,O-bindentate directing assisted Pd-catalyzed intramolecular amination reactions. Various benzoxazinone derivatives are obtained in moderate to good yields. The directing group can be removed under mild condition, highlighting potential synthetic utility of this method.
Zhou Panpan , Guan Mingyu , Zhang Jingyu , Xu Fan , Zhao Yingsheng . Facile Synthesis of Benzoxazinone Derivatives via Palladium Catalyzed Intramolecular Amination[J]. Chinese Journal of Organic Chemistry, 2017 , 37(8) : 2028 -2033 . DOI: 10.6023/cjoc201703012
[1] Sawada, Y.; Yanai, T.; Nakagawa, H.; Tsukamoto, Y.; Yokoi, S.; Yanagi, M.; Toya, T.; Sugizaki, H.; Kato, Y.; Shirakura, H.; Watanabe, T.; Yajima, Y.; Kodama, S.; Masui, A. Pest Manage. Sci. 2003, 59, 36.
[2] (a) Anderluh, P. S.; Anderluh, M.; Ilaš, J.; Mravljak, J.; Dolenc, M. S.; Stegnar, M.; Kikelj, D. J. Med. Chem. 2005, 48, 3110.
(b) Rajitha, C.; Dubey, P. K.; Sunku, V.; Piedrafita, F. J.; Veeramaneni, V. R.; Pal, M. Eur. J. Med. Chem. 2011, 46, 4887.
[3] Macchiarulo, A.; Costantino, G.; Daniele Fringuelli, D.; Vecchiarelli, A.; Schiaffella, F.; Fringuelli, R. Biol. Med. Chem. 2002, 10, 3415.
[4] (a) Feng, R.; Houseman, J. G.; Downe, A. E. R. Pestic. Biol. Physiol. 1992, 42, 203.
(b) Campos, F.; Atkinson, J.; Arnason, J. T.; Philogéne, B. J. R.; Morand, P.; Werstiuk N. H.; Timmins, G. J. Chem. Ecol. 1988, 14, 989.
(c) Campos, F.; Atkinson, J.; Arnason, J. T.; Philogéne, B. J. R.; Morand, P.; Werstiuk N. H.; Timmins, G. J. Chem. Ecol. 1989, 15, 1989.
[5] Huang, M. Z.; Huang, K. L.; Ren, Y. G.; Lei, M. X.; Huang, L.; Hou, Z. K.; Ou, X. M. J. Agric. Food. Chem. 2005, 53, 7908.
[6] Holly, F. W.; Cope, A. C. J. Am. Chem. Soc. 1944, 66, 1875.
[7] (a) Russell, V. M.; Koenig, J. L.; Low, H. Y.; Ishida, H. J. Appl. Polym. Sci. 1998, 70, 1413.
(b) Shen, S. B.; Ishida, H. J. Polym. Sci., Part B:Polym. Phys. 1999, 37, 3257.
(c) Takeichi, T.; Kawauchi, T.; Agag, T. Polym. J. 2008, 40, 1121.
(d) Xiang, H.; Ling, H.; Wang, J.; Song, L.; Gu, Y. Polym. Compos. 2005, 26, 563.
[8] Hamilton, R. H.; Bandurski, R. S. Cereal Chem. 1962, 39, 107.
[9] (a) Zuniga, G. E.; Argandona, V. H.; Niemeyer, H. M.; Corcuera, L. J. Phytochemistry 1983, 22, 2665.
(b) Erich, G.; Wolfgang, E.; Bacher, A.; Frey, M.; Gierl, A. Phytochemistry 1997, 45, 715.
[10] (a) Rajachandrashekar, V.; Vineel, B. G.; Venkataiah S. Pharm. Chem. 2014, 6, 7.
(b) Rajitha, C.; Dubey, P. K.; Dubey, P. K.; Sunku, V.; Veeramaneni, V. R.; Pal, M. J. Heterocycl. Chem. 2013, 50, 630.
(c) Armitage, M.; Bret, G.; Choudary, B. M.; Kingswood, M.; Loft, M.; Moore, S.; Smith,S.; Urquhart, M. W. J. Org. Process Res. Dev. 2012, 16, 1626.
(d)Macías, F. A.; Marín, D.; Bastidas, A.O.; Chinchilla, D.;Simonet, A. M.; Molinillo, J. M. G. J. Agric. Food Chem. 2006, 54, 991.
(e) Ramesh, C.; Raju, B. R.; Kavala, V.; Kuo, C. W.; Yao, C. F. Tetrahedron 2011, 67, 1187.
(f) Gangloff, A. R.; Brown, J.; Jong, R.; Dougan, D. R.; Grimshaw, C. E.; Hixon, M.; Jennings, A.; Kamran, R.; Kiryanov, A.; Connell, S.; Taylor, E. J. Biol. Med. Chem. Lett. 2013, 23, 4501.
(g) Sams, A. G. Hentzer, M.; Mikkelsen, G. K.; Larsen, K.; Bundgaard, C.; Plath, N.; Christoffersen, C. T.; Andersen, B. B. J. Med. Chem. 2010, 53, 6386.
[11] (a) Sharifi, A.; Barazandeh, M.; Abaee, M. S.; Mirzaei, M. Terahedron Lett. 2010, 51, 1852.
(b) Brahma, K.; Das, B.; Chowdhury, C. Terahedron 2014, 70, 5863.
(c) Konda, S.; Raparthi, S.; Bhaskar, K.; Munaganti, R. K.; Guguloth, V.; Nagarapu, L.; Akkewar, D. M. Bioorg. Med. Chem. Lett. 2015, 25, 1643.
(d) Borate, H. B.; Maujan, S. R.; Sawargave, S. P.; Chandavarkar, M. A.; Vaiude, S. R.; Joshi, V. A.; Wakharkar, R. D.; Ramkilyer. Bioorg. Med. Chem. Lett. 2010, 20, 722.
[12] Zuo, H.; Li, Z. B.; Ren, F. K.; Jalck, J. R.; Meng, L. J.; Ahn, C.; Shin, D. S. Terahedron Lett. 2008, 64, 9669.
[13] Chen, D. B.; Shen, G. D.; Bao, W. L. Org. Biomol. Chem. 2009, 7, 4067.
[14] Min, E. Z.; Wu, W. Green Chemistry and Chemical Engineering, Chemical Industry Press, Beijing, 2000, pp. 22~24(in Chinese). (闵恩泽, 吴巍, 绿色化学与化工, 北京, 化学化工出版社, 北京, 2000, pp. 22~24.)
[15] (a) Zaitsev, V. G.; Shabashov, D.; Daugulis, O. J. Am. Chem. Soc. 2005, 127, 13154.
(b) Shabashov, D.; Daugulis, O. J. Am. Chem. Soc. 2010, 132, 3965.
[16] (a) Kim, J.; Sim, M.; Kim, N.; Hong, S. Chem. Sci. 2015, 6, 3611.
(b) Castro, L. C. M.; Chatani, N. Chem. Eur. J. 2014, 20, 4548.
[17] Chen, G.; Shigenari, T.; Jain, P.; Zhang, Z. P.; Jin, Z.; He, J.; Li, S. H.; Mapelli, C.; Miller, M. M.; Poss, M. A.; Scola, P. M.; Yeung, K. S.; Yu, J. Q. J. Am. Chem. Soc. 2015, 137, 3338.
[18] Guan, M. Y.; Pang. Y. B.; Zhang, J. Y.; Zhao, Y. S. Chem. Commun. 2016, 52, 7043.
[19] He, G.; Lu, C. X.; Zhao, Y. S.; Nack, W. A.; Chen, G. Org. Lett. 2012, 14, 2944.
/
| 〈 |
|
〉 |
