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

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）...

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Published inChinese chemical letters Vol. 28; no. 6; pp. 1243 - 1247
Main Authors Wang, Peng, Liu, Fei, Zhong, Qiu, Zheng, Shi-Long, Chen, Yue, Wang, Guang-Di, He, Ling
Format Journal Article
LanguageEnglish
Published NEW YORK Elsevier B.V 01.06.2017
Elsevier
Subjects
Antiproliferative activity
Benzoxazinones
Chemistry
Chemistry, Multidisciplinary
Copper catalysis
Intramolecular amination
Physical Sciences
Science & Technology
Triazol-3-amid
Intramolecular amination
Triazol-3-amid
Benzoxazinones
Antiproliferative activity
Copper catalysis
INSERTION
AMIDATION
C-H BONDS
FUNCTIONALIZATION
SEROTONIN REUPTAKE INHIBITORS
SUBSTITUENT
AMINATION
2H-1,4-BENZOXAZIN-3-(4H)-ONES
AZIRIDINATION
5-HT1 RECEPTOR ANTAGONISTS
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Summary: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.
Bibliography:11-2710/O6
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
ISSN:1001-8417
1878-5964
DOI:10.1016/j.cclet.2016.12.028