Man‐Yun Liu, De-Qing Shi
Mar 1, 2014
Citations
1
Influential Citations
4
Citations
Journal
Journal of Heterocyclic Chemistry
Abstract
A series of novel N-{5-[2-(4,6-dimethoxy-pyrimidin-2-yloxy)-phenyl]-[1,3,4]thiadiazol-2-yl}2-aroxy-propanamides were designed and synthesized by the multistep reactions. 2-(4,6-Dimethoxy-pyrimidin-2-yloxy)-benzaldehyde (1) reacted with aminothiourea to yield 2, which undergoes ring closure to give 5-[2-(4,6-dimethoxy-pyrimidin-2-yloxy)-phenyl]-[1,3,4]thiadiazol-2-amine (3) in the presence of ferric chloride in refluxing ethanol. 3 reacted with 2-aroxy-propionyl chlorides to give the target compounds 4a, 4b, 4c, 4d, 4e, 4f, 4g, 4h, 4i in moderate to good yields. Their structures were confirmed by IR, 1H-NMR, EIMS, and elemental analyses. The preliminary bioassay indicated that some of them displayed moderate to good selective herbicidal activity against Brassica campestris L. at the concentration of 100 mg/L. However, these compounds did not possess inhibitory activity against Echinochloa crus-galli at the tested concentrations.