Citation: Wang Peng, Liu Fei, Zhong Qiu, Zheng Shi-Long, Chen Yue, Wang Guang-Di, He Ling. Chemoselective synthesis and cytotoxic activity of a series of novel benzo[1, 4]oxazin-3-one derivatives[J]. Chinese Chemical Letters, ;2017, 28(6): 1243-1247. doi: 10.1016/j.cclet.2016.12.028 shu

Chemoselective synthesis and cytotoxic activity of a series of novel benzo[1, 4]oxazin-3-one derivatives

Wang Peng ^a ,
Liu Fei ^a ,
Zhong Qiu ^b,c ,
Zheng Shi-Long ^b,c ,
Chen Yue ^d ,
Wang Guang-Di ^b,c,, ,
He Ling ^a,,

a.
Key Laboratory of Drug-Targeting and Drug-Delivery Systems of the Ministry of Education, Department of Medicinal Chemistry, West China School of Pharmacy, Sichuan University, Chengdu 610041, China
b.
RCMI Cancer Research Center, Xavier University of Louisiana, New Orleans 70125, USA
c.
Department of Chemistry, Xavier University of Louisiana, New Orleans 70125, USA
d.
Department of Nuclear Medicine Affiliated Hospital, Luzhou Medical College, Luzhou 646000, China

Corresponding author: Wang Guang-Di, gwang@xula.edu He Ling, lhe2001@sina.com
Received Date: 20 September 2016
Revised Date: 8 November 2016
Accepted Date: 28 November 2016
Available Online: 8 June 2016

Figures(4)

That tetraacetonitrile copper perchlorate catalyzes intramolecular amidation of arenes was found to be a new strategy for construction of nitrogen-containing heterocycles and resulted in the formation of a series of novel benzo[1, 4]oxazin-3-one derivatives from N-(1, 3-diphenyl-1H-1, 2, 4-triazol-5-yl)-2-phenoxyacetamides. This approach of heterocyclic construction proceeds in a chemoselective manner in which only benzo[1, 4]oxazin-3-one derivatives were obtained by C-N bonds formation with cheap and simple copper salt catalyst under mild conditions in moderate to good yields. The biological assay of some of benzo[1, 4]oxazin-3-one derivatives showed that they had moderate antiproliferative activity toward MDA-MB231 and HeLa cancer cell lines.
- Intramolecular amination,
- Copper catalysis,
- Benzoxazinones,
- Triazol-3-amid,
- Antiproliferative activity
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