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Design, synthesis and biological evaluation of novel 6,7,8,9‐tetrahydro‐2‐(2‐aryloxypyrimidin‐4‐yl)‐2 H ‐[1,2,4]triazolo[4,3‐ a ]azepin‐3(5 H )‐ones
Author(s) -
Wang YiFeng,
Liu WeiMin,
Zhu YouQuan,
Zou XiaoMao,
Hu FangZhong,
Yang HuaZheng
Publication year - 2006
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570430520
Subject(s) - chemistry , yield (engineering) , hydrazine (antidepressant) , elemental analysis , proton nmr , carbon 13 nmr , stereochemistry , medicinal chemistry , combinatorial chemistry , organic chemistry , chromatography , materials science , metallurgy
A series of novel 6,7,8,9‐tetrahydro‐2‐(2‐aryloxypyrimidin‐4‐yl)‐2 H ‐[1,2,4]triazolo[4,3‐ a ]azepin‐3(5 H )‐ones were designed and efficiently synthesized. Their structures were determined by IR, 13 C and 1 H NMR, mass spectroscopy, and elemental analysis. These compounds were screened for herbicidal activities against rape and barnyard grass. Compounds 5a‐5f and 5m exhibited moderate herbicidal activity against rape. In addition, the synthesis of the intermediate 1‐(azepan‐2‐ylidene)‐2‐(2‐chloropyrimidin‐4‐yl)‐hydrazine ( 3 ) was studied and the reason for the low yield in the initial procedure is discussed as well.